26 August, 2014

How to Keep Your Friends

Table of Contents

How to Keep Your Friends


Part 1: Building a Great Network

Structural Analysis of One’s Social Network

The Environment Factor

How to Be a Good Friend

Starting with Generosity

Building Trust

Showing Gratitude

Establish Relevancy

Part 2: Planning Social Interactions

Planning a Date

On Spontaneity

Argument for 1-on-1 interaction

If you must go threesome or more

Post Date Procedures

Handing Out Rejection

Part 3: Increasing Your Collision Rate

Liking Their Facebook Posts

Offering Help

Asking for Help

Asking Them For Advice

“…Reminded me of You”

Going to High Collision Places

“My Calendar Told Me To Say Hi to You”

Inviting Yourself to Events

Some Softwares for Staying in Touch with Friends

Bonus: Advice for Incoming Freshmen

Conclusion: Make Time for Your Friends!

How to Keep Your Friends

Keeping your friends is difficult. I have made quite a number of friends (and I’m sure you have too), but I really haven’t been able to stay in touch with a majority of them. My Facebook was like a graveyard of past relationships, a relic of my former social life. There is a plethora of resources online and in print that teaches you how to make friends, and I think they’re worth a read. However, I haven’t seen many (if any) materials that focus specifically on retaining your friends, and I think keeping one’s network of friends is important. I’ve had a lot of trouble keeping in touch with everyone, and often I have lost friends because of my ineptitude to stay in touch with them. I don’t want this to happen to people. I want everyone to cherish the friendship and connections they have and be able to scale the size of their networks without compromising the quality of each relationship. If people stopped losing the friends they have, then people wouldn’t feel so lonely to compel them to constantly seek new friends (although new friends are always nice)!

If you ever feel like you’re not as close to your high school friends, this guide is for you.

If you ever bump into someone you lost touch with and have to make that awkward decision on whether or not to pretend to know then, then you should read this.

If you’re in a new environment and are making tons of friends, this is for you too.

If you share the struggles of staying in touch with everyone and want to keep new friends you meet, read on!


Maintaining a Social Network could be crudely broken down into three parts of the guide. Being a good friend, planning out social interactions, and increasing your collision rate.

Part 1: Building a Great Network means creating a social network that is fairly low-maintenance. A bad network could mean spending all your time with your time catering to a specific person or group you don’t particularly fit in with. A great network is a network in which someone who can resume the same level of intimacy and friendliness with his friends even after a hiatus of not seeing each for a while or keeping a distance away. A bad network is one in which you constantly lose touch with people left and right, and people thinking you don’t want to be friends with them.

Part 2: Planning Your Social Interaction is a new form of handling one’s vast social network. This isn’t an Amish community anymore, you’re no longer just dealing with the 150 people in your village, your network could span hundreds to possibly even thousands of people. You have to find some way to organize everyone. Well, thank goodness for Google Calendar (or whatever calendaring software you use). Social interactions are much more manageable now that you know exactly who to reach out to and when. Never forget an appointment and never lose a friendship.

Part 3: Increasing Your Collision Rate: Having to keep everyone on your forefront of your head is very hectic. How does one remember how to stay in touch with someone? What are some easy ways to keep cycling through various peoples in your lives? How do you increase your “bumping into” rate?

Note: My personal objective for writing this guide is to inform the general public because I think it’s valuable knowledge. Another more selfish reason is that I hope my old friends and possibly strangers read this and reach out to me so I don’t have to do all the work reaching out to them. So if you would like to talk to me, please do so! I’m friendly!

Let’s start!

Part 1: Building a Great Network

Not everyone can start at this point, but if you’re still building a network or if you’re still meeting new people (which you always should anyways), it is always better to set the initial relationship as a friendly and maintainable one. This section starts off with a discussion of the structure a good social network, followed by the meat of this section on how to be a good friend that makes you accessible, trusted, and remembered.

Structural Analysis of One’s Social Network

Most individuals either choose to have several close friends that they always hang out with, or have tons of acquaintances that that they cycle through. Each network has its advantages and disadvantages.

Having close friends is no doubt essential to one’s social and personal well being.  They are most likely there for you when you are sick or if you need a ride from the airport. They are very emotionally accessible, which means you can comfortably talk to them without a long “easing-in” time. They have a strong relevancy in the forefront of your mind and theirs. You guys spend a lot time with each other.

However, the most important disadvantage to having a circle a close friends is the fragile nature of these relationship when things go wrong. For example, I noticed that people may make bad choices in choosing their “close friends”. Many times the foundation of a close friendship is structurally unsound. For example, a friendship built on prior history is unlikely to last, like childhood friends who grow up with vastly incompatible personalities and interests. They may stick together because “they’ve been best friends since 2nd grade,” but that shouldn’t be the main reason why person A would want to be with person B. Another foundational trap people may fall through when deciding close friends is people’s desire for comfort. A friend may not be your close friend, but he’s the closest relationship you got, so therefore you call him your close friend. Another friend you may not particularly like, but he lives on your floor or he’s in your class so he’s accessible. I don’t think this is a good model for choosing your close friends. If you fall into these traps, you can end up in subpar relationships. Not only that, due to your complacency in the relationship (desire for comfort exceeds desire for quality friendships), you’re less likely to look for new connections that can save you from your disastrous relationships.

Only having a group of close friends is dangerous because the consequences of anything going wrong compounds the damage multifold. Suppose you date someone within your group of friends, and you break up. Now, if this causes friction within your circle of friends and you become ousted by the group, you have much less social support since you didn’t take the time to build other connections. Similarly, this is the main reason why the November rule exists. The November rule is an unspoken rule in most college campus that roughly follows the saying: “Never date a freshman until November 1st of the school year.” The idea is that if a freshman jumps into a relationship so early in their educational career without building a robust network of friends, they are likely to suffer more if the relationship goes awry due to the lack of social investment. The other reason is the misattribution fallacy, which means the excitement of novel experiences is misdirected at an individual, believing that their lover is the source of the physiological arousal, but I digress.

Taking a grim example, stability is often the justification individuals in abusive relationships use. They tend to incorrectly believe that at least they’re with someone or that they couldn’t do any better. The thought of being alone scares them enough to choose to deal with a bad relationship than try a new one. I think having close friends is so important that one should not put up with unsatisfactory relationships. 

Jumping to the other end of the network quality spectrum is the “acquaintances with everyone, friends with none” guy. A wide-network can be useful since your network reach tends to be span very widely across various groups. It solves the problem of only having a small group of friends. If things go wrong, you can just join a different group, or hang out with different people.

At the same time, these types of networks tend to spread resources particularly thin and damage each individual relationship. It’s hard to devote much time to anyone and most relationships end up only skin deep. These individuals, who don’t belong in any one group, can actually feel much lonelier in group settings even if they’re surround by people they know. They lack the intimacy and closeness of developing stronger friendships, and therefore constantly have trouble finding someone to connect to. They tend stick to formalities like the “Hello! How are you doing? Fine. Thank You. Bye” routine when they see their friends. If you employ a large-spanning social network, be prepared to be excluded from a lot of group events, gossip, and “bonding  time” because people assume you’re not really part of their group, you’re just a social butterfly.

I current have a social network that is a good mix of friends whom I’m extremely close to as well as a fairly large accessible network. I employ Pareto’s principle when it comes to friends. I roughly spend 80% of my time with 20% of my friends, and divvy the rest of my time with the rest of my friends. Most of trouble with maintaining this network comes from staying in touch with the larger outer circle of friends that I don’t spend as much time with. Part 2 and Part 3 of the guide are the most directly relevant sections to the “outer circle” of friends.

The Environment Factor

Contrary to what many people tell you, environment plays a big role in how your social life is structured. The size and quality of your social ecosystem forces you to adapt in certain ways. This will be most notable in Part 3: Increasing Your Collision Rate, but will also touch upon Part 2. Just to illustrate the point using an example, consider the difference between living in a college setting versus a working setting. You are less likely to bump into a fellow friend when you’re working, and more likely than not coordinating activities will be more difficult (fewer clubs, longer distances between individuals). I’m not going to enumerate the ways to adapt to each environment or demographic. I trust in your intuition on what it takes to adjust accordingly. If you have questions, you can ask me :)

How to Be a Good Friend

Being a good friend is so integral to one’s relationship health because it withstands the tests of distance, time, and other complications. Being a good friend means people are comfortable talking to you after 2 years of silence. It means your friends will approach you to talk about sensitive or vulnerable issues. Vice versa, it entails you having less friction to reach out to people. Overall, it means you maintain similar levels of intimacy from each successive meetings, independent of distance, time, and other complications.

Starting with Generosity

One of the key points to building great friendships is to offer help. My friend Gerald has once told me to build a network out of generosity, not out of potential benefits. When those words came out of Gerald’s mouth, I thought it was more agreeable but less doable. “What can I offer to others that will be valuable to them?” I thought. But you would be surprised. Generosity doesn’t always have to come in the form of financial benefits or “networking.” In 90% of the friendships I’ve made, “generosity” simply comes from your ability to listen to their problems and to empathize with them. We are stuck in such a self-centered and narcissistic culture that we failed to consider the feelings and problems of others. So many people just want someone to listen, and this indulgence is something everyone can provide but rarely anyone does.

Once I got the chance to catch up with my friend Alton, and before I could even talk about our personal lives, he asked me what are some of the problems I have right now. I told him my problems, and I told him there wasn’t much he could do to help me. He knew he couldn’t do much to help my personal issues, but he actually sat down, took out a piece of paper, and tried to see how I could tackle this personal problem. I felt so grateful after the meeting and I went back to talk to him about why he chose to help me. He said, “Shortly after meeting someone, I will push to find 3 ways in which I can help them.” I never forgot the help I received from him, so I’m sure people you’ve helped are less-than-likely to forget you if you help them too. Also, remember, everyone has problems on their forefront. There is not a single human being who doesn’t have a problem. 

If you want to solidify an acquired facebook friend to more of a close friend, find something actionable and planned out for the next week or so. If it’s someone you want to learn from, ask them if they have a short while for some coffee next week. If it’s a newly met friend, ask them if they want to join you to go swing dancing. If it’s a cute girl (or guy if you’re a girl), make plans then and there to meet up sometime in the future. People have to feel like meeting you isn’t just another facebook friend in their list or a business card in their rolodex. Even if they can’t make the event, they appreciate your offer to include them in your social life. 

Friendship comes from offering friendship. These friendships do much better to stand the test of time and distance. By offering yourself to them at any time or circumstances, they are more likely to reach out to you despite other barriers. A friendship based on something external, like being on the same soccer team or attending the same class and school, is sound only in the premise of the environment. Once the soccer team dissolves or if you both graduate, you’re more than likely going to grow distant from those contacts. When the premise of the relationship is gone, so will your relationship.

Building Trust

Trust is pretty important when it comes to friendships. Yet it could be hard to build. From my personal experiences, people usually are “generous with [their] friendliness, but stingy with [their] trust” (Dale Carnegie). Building trust is actually pretty easy. Just don’t do anything to lose their trust with you. If you’re friendly and genuine, then people are inclined to trust you. You’re not really trying to build trust as much as you are trying not to lose anyone’s trust. You already know how to build trust, I don’t have to tell you. Be accountable, be honest, and don’t betray anyone. That’s all there is to it. When stakes are high, a track record of consistency and trust will be tremendously helpful.

Showing Gratitude

Showing gratitude is so important. People love to hear that they mattered in your life, that they made a positive impact in your lives. I sure as hell do. That’s how the yearbook industry stays in business. Students pay exorbitant prices for yearbooks every year just so they can run around and fish for thank you notes from their peers. After paying probably upwards of $500 on yearbooks throughout my academic life, I’m sitting here thinking, 1) Why do I have to pay $100 to receive and give thanks to people 2) Why do I have to wait until the end of the year to show my gratitude to my friends and family? 

Why aren’t yearbooks and Thanksgiving runions as effective at building friendships as they should be? Not that they aren’t but there are some flaws. Having artificial reminders and specific time periods to give thanks often makes give gratitude a formality rather than an organic response. If someone shoves a yearbook in your hands, you are more than inclined to write something thankful rather than not. When it’s Thanksgiving, you’re more likely to remember to thank your friends. They would still appreciate your yearbook comment on that time he helped you on your homework assignment, but wouldn’t he have liked that note more when he didn’t expect it and when the gratitude was still relevant?

Show gratitude, and be specific. Saying “Thanks” is a formality that has deteriorated into a knee-jerk response. Saying “Thank you so much for helping me out with that math problem. A similar problem showed up on the test and I knew exactly how to solve it. You really did me a solid.” is much more specific and memorable to the individual. Don’t be a leech, offer help in return! The previous response should be followed by a generous offer like “if you ever need help with your English essay [or whatever you can offer him]. Let me know!”  If you lack skills, offer to buy them their next cup of coffee or lunch. They will be more likely to help you or appreciate your friendship. My old roommate used to bow to me every week or so or give me a hug to thank me for being his roommate. I’m always so flattered, and it gives depth to the relationship past simply being roommates. 

Establish Relevancy

Many people fail to convert a casual encounter into a lasting friendship. Consider when I meet someone at a party. I get along with one of the hosts of the party. I was nice to them, I built trust (however much I could in a night), I was generally happy for them to be around, yet we never really talked to each other afterwards. What happened?

I see this problem as a failure to establish relevancy in a relationship. More likely than not, in most one-time encounters, you’re going to forget why you should see this person again. Part of the reason is that we never really established what future encounters would entail. Is it naturally implied that because we attended a party together, that we should continue to be friends the next day? No, not necessarily.

So it is your responsibility to establish relevancy in a relationship. Why should you ever want to see him again? Why should he ever want to see you again? Make it an essential point to establish a reason to see them again, or at least keep in touch with them. The easiest way for me to establish relevancy is to define a relationship. What is my future relationship with this individual? Is it a mentor-mentee relationship? Is it a potential romantic relationship? Soccer buddies? Business partners? Partners in crime? Although most close friends tend not to fall so neatly into individual categories, it’s a quick and dirty way to get the ball rolling on friendships. I generally suggest future interactions based on this pre-defined relationship.

Here are some examples that illustrate establishing relevancy in a given context



– “Hey, mind if I ask you questions about buying clothes if I have any?”

– “Hey, if you ever need help with website-design. Let me know, okay?”

Potential Romantic Relationship:

– “I would like to get to know you better. Let’s get coffee sometime.”

– “I like ____ too! Let’s go _____ together!”

Business Partners:

– “Hey do you want to meet up a separate time to talk about this awesome idea I have?”

– “I might need your help with this one part of my project.”

– “Let’s talk next week and sort out where our interests may align.”

Common Interests

– “Let’s play league of legends!”

– “Let’s play frisbee!”

– “Let’s study together!”


Really you can say anything (within reason) that offers a future engagement. At the very least, it associates you with something memorable for the other person. If you say you’re good with Excel, your new friend will remember you next time he’s making a spreadsheet. If you like Lana Del Rey or Snoop Dog, you’re more likely to come to mind when your friend purchases Outside Land tickets. Engage to meet up with them sometime in the next week or so. That will be the optimal time between the first and second encounter. 

There are other tips for building a strong foundation for a friendship as well, which I will cover some time in the future. Frankly, there are tons of books and resources on how to make friends. Offering generosity, building trust, showing gratitude, and establishing relevance are probably your four best tools for making strong friends. If you master those four qualities of a good friend, you’re already 90% of the way there.

Part 2: Planning Social Interactions

I’m a big advocate of staying in touch with friends more methodologically rather than free form. The key is that you have stay organized but flexible. I’ve made many mistakes in which my friends relied on me to reach out to them, to which I disappointed them so dearly that I’ve managed to lose contact with many of them. One example is when you bump into your friend on the street. You guys exchange greetings, and before you guys part, one of you says, “Hey let’s hang out some time!” “Of course!” Is usually the typical response. After your interaction, nothing happens. Here’s a table of what will happen based on your choice of action.



Remember, Waiting

Remember, Followup





Remember, Waiting




Remember, Followup





So you’re on the column side and you have three choices: Forget, Remember and wait, or Remember and Followup. Your friend, symmetrically, has three options as well. The results are the cross reference cell of the two chosen actions.

Commentary on each cell:

(1): You both forget to follow up with each other. No biggie. No one’s feelings is hurt. But is that actually true? Once you remember in the future (perhaps when you do want to hangout or want something from them), you’ll remember the moment when you guys said you would catch up, but never followed through. Now you don’t know whether you’re in square (1) or (2) because you don’t know whether your friend was waiting for you to follow up or not. They could’ve forgotten you too, which signals to you they don’t want to hang out with you. They could have been waiting for your initiative to ask them to go your to the party, but felt rejected when you never reached out. It’s never good to forget. Your ass could only be saved if your friend reaches out to you to invite you to his next event.

(2): Your friend is butt hurt because you didn’t call him back or invite him to that event you went to. He feels betrayed because he spent his Friday night flipping through the Facebook photos you posted at that party he wasn’t invited to. Friendship broken. One would think it’s not a big deal, and that your friend is being bitter about it, but it’s really painful to be excluded, so much so that psychologists have found similar areas of the brain activated by rejection and physical pain.

(3): Your friend is a saint. He saved your ass by inviting you to play frisbee.

(4)/(5): You’re waiting for your friend to reach out to you. You don’t know whether he forgot or actually doesn’t want to hang out with you. You spent sleepless night wondering whether he’s really your friend or just there exchanging formalities when he bumped into you.

(6): Your friend once again followed through with his promise. You love him more because you were doubting his friendship for a second there but now you know you’ll be true friends forever

(7): You reach out to your friend, who forgot about your promise. If he actually doesn’t want to hang out with you, that’s fine. If he does, then you guys have a date!

(8): You call your friend, who picks up on the first ring because he was expecting you to invite him to your new house party. He feels grateful he wasn’t excluded.

(9): You guys are both bros/gals and deserve medals!

For much of my life, I’ve managed to fall into the 1,2,4,5 cells. I ended up in 1 and 2 because I don’t have very good organization skills. Sometimes 4 and 5 occur because I don’t have anything planned or because I was hoping they would invite me to their parties, without contributing my social life as well.

In short, it was a disaster. Since I have a resting bitch face, often times when people see me and realize I fell through on my promise to hang out with them, they look at my bitch face and think to themselves “James doesn’t want to hang out with me. He’s just yanking my chain.” And there goes a friendship.

Planning a Date

Since most of your friends are so unorganized and commonly forget to catch up and meet up with people, you’re going to be the one reaching out and doing most of the work. Don’t worry, it’s actually not that much.

Let’s start at the point when you and your friend bump into each other, and now you are about to part. The conversation should end like this on your side (if it doesn’t, you initiate it like this):

Lines are numbered for future references 

1 You: “Hey I gotta go soon, but let’s catch up sometime!”

2 Your friend: “Yeah! Definitely!”

3 (Usually the conversation ends there and you guys part, but you’re going to take initiative right now).

4 You: “How does tomorrow for lunch at the dining commons sound for you?”

5 Your friend: “Oh, sorry, I have a midterm on Thursday I really gotta study for.”

6 (Now you feel disappointed and will probably say “Oh, that’s ok, let’s do some other time then.” Instead you will say)

7 You: “Oh that’s understandable. You gotta study when you gotta study. When are you going to be available?

8 Your friend: “Oh. I don’t know yet. I have to hear back from my boss’s work schedule. He won’t get back to me until later this week.”

9 You: “Sounds good! I’ll check back in with you on Friday then!”

10 Your friend: “Sounds great! Bye!”


Here is some commentary on the social interaction. This is probably a worst-case scenario so you know how to handle it properly.

 1: You are initiating interest in your friend. You are reaching out to him to basically want to spend more time with him. He will most likely be flattered at your request.

2: Your friend agrees to this arrangement. Even though he says “Yeah! Definitely!” all excited, he’s probably too lazy to try to set anything up himself. You know how people are.

3: Here’s a potential breaking point where you might lose him. People tend not to do very well with setting up dates. The whole “What should we do? Where should we go? When should we do this?” boyfriend/girlfriend scenario sets up. And most of the time people are too lazy to figure out the details. It’s not the limited choice that usually creates a deadlock, but rather the paralysis of choice. You’re going to break through the static and take leadership.

4: You offer a concrete lunch date. It’s hard to reject a lunch date. Everyone’s gotta eat some time right? It’s better to eat with someone than without. If time’s too pressing, offer a 15 minute coffee break or talk. The idea is a low-commitment, get-to-know-each-other get together. Offering a concrete time and location allows him to set up a date just by saying “yes.” Otherwise, you would have to discuss all available options, and that results in too much stalling for making official plans.

5: Your friend pushes you aside again. Try to collect your nerves and not get angry at him. Unavailability is usually not a sign of malice, as much as rejection hurts for us. Offer him another option.

6: A lot of people lose steam here too. “Let’s put it on the backburner” usually leads to a deadend. Nothing’s going to remind you to get a date going again. He’s obviously too lazy to set anything up, and now you are too. So you have to ask him for his availabilities.

7: Now the ball’s at his court, he’ll give you a list of options, in which case you can pick and choose one and work from there.

8: Your friend throws a curveball. Not knowing?! Yep, that’s most young adults for you. Even most adults have an agenda that only extends to the next meal. He’s probably sensing that you’re either too clingy or trying really hard to reach out to him. He’s probably either creeped out or flattered.

9: Calm his nerves a bit by saying, “that’s ok,” it’s not that big of a deal. Focus on the positives, leave him an option and tell him to keep his head up for open slots reserved for you. Tell him you’ll check back in again when he knows. He doesn’t want to do any of the work.

10: You guys say goodbye.

Now this is the worst case scenario (A simple “no” would’ve been a lot clearer than trying to figure out his intentions). If your friend continually pushes back, he/she might actually be too busy to hang out with you, and that communicates to you that he/she is too busy to have a friendship, and doesn’t want to hang out with you. That’s is the worst of the worst cases.


In each of these steps there is a potential outlet for advancement, and that’s where your Google calendar comes in. 

Now looking at the bright side. If you friend says yes at:

4: Awesome! You have a date. Put this calendar appointment on your Google calendar so you don’t forget to attend.

8: If he gives you a list of times available. It’s also good to check in to see when you are available as well. Plan accordingly and set up something on your calendar.

10: If all else fails, you promised to check back in with him some time in the future. Put this future date on your calendar so it can remind you to check back in with your friend. Look up Google Tasks or Remember The Milk for task lists.

The beauty of this integration is that it takes literally 10 seconds to check in with someone over Facebook. You will know exactly when to check in, and hardly anyone would flake an appointment in the future. You’re not forgetting anyone and you’re not pressuring anyone into going out of their way to hang out with you. 

If you however, miss out your friend in any of those 10 lines, you are lost, and have to do something (usually more taxing) to recuperate to revive your friendship.

Google calendar is your friend. When you have to keep track of multiple people, this tool comes in really handy. 

On Spontaneity

I expect some to react to this framework with distaste, the main argument being that it effectively kills spontaneity and organic development in a relationship and reduces the relationship to something akin to a weekly chore.

I disagree. And I’ll address these points.

“Planning kills spontaneity”

No it doesn’t. Who says you had to choose one or another? You can have both. Planning ahead solves the pain point of not having an organized way of making time for your friends. If you want to hang out with friend A, but have to study for a test right now, it would be more advisable to make plans in the future (or else you might forget later). I’m not trying to make a claim on which system is superior. I just want to point out that the question inherently assumes that they’re mutually exclusive when in reality you can have both. Make spontaneous plans too if that’s more suiting for you. I never told you to stop doing that.

“Planning kills organic development”

What does relationship development mean to you? It is measured in the number of hours spent together? Or the number of stories you share with each other? Or could it not be measured at all? Planning is the precursor to relationship building. Planning facilitates the process of having more face-to-face interactions, nothing more, nothing less. It does not touch much less dictate the contents of the meeting. That is all up to you. The fear of inorganic is well founded, but only on the basis of the interaction. Planning is a minor part of relationship development, and only concerns itself with making face-to-face time happen.

“Planning reduces the relationship to something akin to a weekly chore.”

Like the previous argument, planning does dictate the contents/results of an interaction. If making the effort to meet your friends feels like a chore, maybe it’s time to reevaluate what people you would want to consider as friends worthwhile of your time and effort. 

Once again, I’m not condemning spontaneity. This is a false dichotomy. You can have both planned and spontaneous interactions with your friends. I do too! I cancel plans to play late-night frisbee, I call friends 30 minutes before I’m heading to the beach. I move around my schedule to accommodate an interesting conversation that extended past my allotted time. I plan if I can’t be spontaneous, and I’m spontaneous if the situation seems fit.

Argument for 1-on-1 interaction

I’m a big advocate for the 1-on-1 interaction. Bro-dates or just a normal friend date. It takes out a lot of the complexity with group dynamics and allows your conversations to go past skin deep. Basically 1-to-1 interaction grants you more freedom and allows you to give all your attention to the person across the table. It’s also a lot less of a hassle to plan when you’re only working with two schedules.

If you must go threesome or more

If you must, here’s my suggestion: start with two people. Once you have a time/location set up, then invite other people. That way you know something will happen no matter how many people show up, and you don’t have to keep track of so many people’s schedules because it’s either you can attend, or you can’t. Groups tend to be indecisive, so start small, and expand and make changes necessary. Once again, having to organize everything together is tough, but doable.

Another difficulty you must face when it comes to groups is that you have to be aware of group dynamics. There’s always a 3rd, 4th, 5th, nth wheel out there. You do not want to exclude everyone. You have to make sure everyone feels like they belong there. That means engaging them even though they are quiet or shy.

Groups are less conducive to deeper conversations, so when you’re in a large group, focus more on having fun and building bonds through activities than through conversation. Remember, your attention is divided so it’s hard to cater to everyone’s emotional needs. Narrow the emotional spectrum band and just focus on the positives.

Post Date Procedures

I generally follow up with a quick thank you after the date. I reference a couple of points (or inside jokes) that came up during the date. It continues to establish the relevancy of the relationship. If I have something planned for the future with this friend (like a future concert I would like to attend with him or another event), now is usually the time I start inviting him. Otherwise, I put a task item with his name 2-3 weeks into the future, just to remind me to check in with him. What this prevents is false closure. False closure is the feeling that we ended on good terms. Yes, we ended a hangout on good terms, but often that implies that we don’t need to hang out anymore, or that all that is to say has been said. Not true! Like making new friends, it’s easy to forget to keep in touch with them in the future. Remind your future self to say hi and catch up again!

Handing Out Rejection

Every so often, you reject someone who in turn believes you don’t want to hang out with them. That’s most likely not your case. You probably made prior plans or have a commitment or simply am not interested in doing a particular activity with them. I’ve certainly have trouble rejecting people in fear of them either taking offense or retaliating (not inviting me to events). I try my best to let them down easily. Here are some tips:

  • Thank them for inviting you: Showing gratitude to your friends shows that you value them as a friend and sincerely appreciate their invitation to want to spend more time with you.

  • Be Honest, Be Firm: Trying to lie your way out of hanging out with someone is not only dishonest in building a relationship, it’s also really hard to pull off. Being honest and being firm communicates 2 points to your friend. 1: I value this relationship, which is the reason why I know I can be honest and straightforward with you and 2: I’m rejecting the proposal, I’m not rejecting you as a person. Sometimes it helps to say those exact words.

  • Don’t be Condescending: “Oh that’s so cute, Sally wants to hang out with me.” People get very offended when you become condescending in your rejection. You are not better than the other person. No one is begging on their knees to hang out with you, so don’t act like it’s so.

  • Offer a Substitute: If you rejected the hangout because you aren’t available that day, ask if they want to hang out a different day. If you don’t like the activity, offer a different activity. Asking people to hang out is like a tennis match, when someone asks you to hang out with them, the ball’s on your court now. Reciprocating an offer shows that you want to hang out with them. People rarely want to act like the desperate ones so usually they will stop asking you after a couple of times (usually just once). If you need to remind yourself, use Google tasks.

Of course if you really don’t want to hang out with the person, ignore my advice. There are people you want to spend time with, and people who you don’t. You don’t need to be friends with everyone.

Part 3: Increasing Your Collision Rate

So you want to find excuses to reach out to people and catch up huh? No one wants someone who reaches out to them out of the blue. It triggers a “salesman” vibe. They often will think “What does James want from me? Maybe he wants me to get him a job or do him a favor.” Don’t worry. Here are some timeless excuses for reaching out to someone after a quiet period.

Liking Their Facebook Posts

You know there is that period in your life when you cared about how many likes you got for your super witty status about how boring your homework is. Well, most people have not grown out of it yet (even me). People will constantly check their notifications to see who has liked their statuses/photos/links/younameit.

Staying on the forefronts of their mind is as simple as clicking a button, the like button. If you want to reach out to them (and trust me, you want to, the benefits are ten folds), send them a Facebook message and ask them if they want to catch up. It comes out so organically they won’t even realized you stalked their profile.

I often take advantage of the reverse situation too. If someone likes my post/photos/links, I can usually use that as an excuse to make plans with them. A like on your status indicates that your presence is felt by the person who liked your content, which introduces a small dose of relevancy that you can use to initiate conversation.

Offering Help

Gerald once told me that he once got free conference tickets for a conference he couldn’t attend, so he spent 10 minutes emailing his friends asking him if they would like to go. Almost no work, but people really appreciated his offer to help.

Although you may not always be given free goods to give away, you can always look for ways to help out your friends. If your friend complain about his homework, ask if he needs help. If you and your friend are meeting up somewhere, offer him or her a ride there and back. A favor as simple as offering to help him clean his room (thanks Patrick!) or “can I get you a cup of water?” shows that you care. 

When you identify ways to help other people without asking for anything in return, people can appreciate your presence and your commitment to keep a relationship healthy. It’s very little effort on your behalf but to them it could make or break them. I got a job offer for an internship over the summer from Google because my friend reached out to me to offer me a referral to their program. He spent 5 minutes writing an email that fundamentally changed my life forever. I had a similar process with Pinterest too. A 2 minute email my friend wrote got me the summer internship I could only dream of. I, too, offer job referrals and opportunities to my friends whom I think would benefit from it. People really appreciate anything you can give them.

Mandatory Nice Guy Note: Listen, you are offering help and giving help because you are a kind and generous person and you value the relationship with the person, not the value the person brings to the table. You can tell a lot about a person by the way he treats the people who don’t have anything material to offer in their lives. If a hiring manager sees a prospective employee compliment his shoes, but treats his secretary like crap, then he knows the person’s only consequentially nice to him to get that job. Similarly, if you treat relationships differently based on how much value a person brings you, most people can easily spot that type of Machiavellian behavior. 

There is a fine line between being kind and being nice. Being nice is a formality, a social ritual, if you will, to obtain an end goal or state. Being kind is a conscious effort to promote your friends and build a relationship.

Asking for Help

Ask for help if you need it. That’s what friends are for right? Being raised in an Asian family for most of my life, I was taught to believe that you should never ask for help from anyone. “We don’t want to owe them anything.” My mother would say, out of goodwill and cultural norms.

But as I grew up I have come to learn that it isn’t necessarily true. Many of your friends genuinely want to help you, it’s a burden that they are willing take on. Just like the previous section, your friends want to offer help to show that they care about you, and when you reject their offer or don’t seek their help, it could actually come off as hostile.

Asking for help demonstrates your vulnerability. It shows that you are human and need other people to make you happy. It offers an opportunity for your friends to show that they matter in your life, by helping you. Playing the image of being “perfect” and “independent” has lost its meaning in a friendship. No one wants a “perfect” friend who doesn’t need anyone. Perfect is an unachievable status that only stinks of inauthenticity and fakeness. The new perfect is perfectly human, and asking for help is one way of showing that you value your friendships.

If people see that you don’t want to owe them anything, then they see it as you seeing the relationship as a transactional relationship. “James doesn’t want him to owe me anything. He think I’m going to ask for something in return.” This breeds distrust, which is not good. It also says “James doesn’t want anything to do with me.” Which is also not ideal. 

Ask for help often! But under 3 conditions. First, you have to show gratitude upon being helped. Your friend is trying to communicate that he cares about you as a friend to do this favor for you, and you should acknowledge his attempt to win your gratitude. If you are truly thankful for him, say it! My friend Anthony calls me about the computer science difficulties he has almost every week, and often I spend a good amount of time helping him through his problem sets. Why do I do it? Because Anthony sincerely shows his gratitude for my help. He says thank you and “that was a lot of help” and texts me heart emoticons. After all these gestures, I couldn’t help but feel appreciated that he looks up to me for computer science help. He asks me because he knows I am willing to help him because I am his friend, and he acknowledges my generosity like no other.

The second condition is to either not ask for favors too often or too big. Asking for too many favors would make your friend think you’re taking advantage of them, so don’t do it so often that it would annoy your friend. Don’t ask for favors too big (or try not to). It’s not that it would ruin a relationship, but it would definitely put strain on it. 

The third condition is to reciprocate. If you’ve been violating the second condition too much, even the debts a bit by giving help back, or offering help back. If you have good friends, they will ask you anyways when they need help. If they are polite, then you should be the one initiating the offer to help. A gratitude followed by an offer to help is usually the best way to go about reciprocating. “Thanks for babysitting my cat. Let me know if you ever need me to babysit your dog. I’d be happy to do it.” That’s good because you’re communicating that you understand that he went out of his way to accommodate you, and you in return, maybe not immediately, are willing to go out of your way to accommodate him as well. Often times I let my friends pay for my meal, because then I get to say, “Thanks for paying for my meal. The next meal’s on me!” Now I’m not rejecting their friendliness, and on top of that, I’ve secured another time to hang out with my friend.

Asking Them For Advice

Being asked for advice is one of the biggest ego boost you can get, and you often can ask for advice from practically anyone. Anecdotally, everyone has something to say about dating, so asking for dating advice always leads to interesting conversations. If not, ask for professional advice. I’ve played the “fanboy of ___” card way too many times on high-profiled entrepreneurs that I’ve gotten free meals and time with them. They always have fewer people reach out to them than you would expect. Like I’ve said before, many people just want someone to listen to. 

Follow the “Asking for Help” conditions as necessary.

“…Reminded me of You”

If something or someone reminded you of another person, it’s probably a good idea to send a quick text or Facebook message informing them rather than letting it slide. It shows that the other person’s still on your forefront and you still think about them. Since it comes organically, it genuinely means they were on the forefront of your mind. 

If you’re reaching out without a reason. Make something up. “I just saw your twin” is nice and easy (although it may prompt the response “pics or it didn’t happen”). “I had a dream about you last night” is more visceral, and even flirty if you want to turn it that way.

Going to High Collision Places

I tend to like to study where I am most likely going to see my friends. I usually end up in my local coffee shop, my dorm lounge, or even my university plaza. If I see a friend. Bam! “Hey how’s it going? Let’s catch up! When are you free?” And there you go, a lunch or dinner date.

Going to high collision places doesn’t just entail studying. Anywhere where you will most likely meet people, go there. Find people, say hi, and make appointments. 

“My Calendar Told Me To Say Hi to You”

Do you know you can practically say anything to hang out with your friends? Yep, in all brutal honesty, I say this sometimes. No one has ever called me out for being inauthentic or mechanical in my methods. They’re usually just happy I thought of them and want to spend time with them.

Inviting Yourself to Events

I always shied away from inviting myself to events. I always assumed that if someone didn’t invite me, it was because they didn’t want me there. I’ve come to understand that that is not always the case. Sometimes people forget and want you there. I myself even forget, even with a methodical system of keeping track of my friends. Other times people are afraid of rejection, and don’t ask you. 

The key though is being able to differentiate between someone who is forgetful versus someone who just doesn’t want you there. Sometimes it is hard to tell. If the person gives me the right cues though, I would see if I could invite myself. It’s an extension that could fail miserably though. 

I have a friend who was going to go backpacking with his group of friends without me, and I felt a bit excluded and hurt because I thought that he didn’t want me there. But after some conversation, it turned out that my friend didn’t realize I was the kind of person who would be down to go backpacking. It was only when I nudged myself into the event that he realized that I would be interested in going.

Some Softwares for Staying in Touch with Friends

Some people prefer taking the software route. I’ve tried some of these. Some I still use, other I get out of touch. I think a simple Google calendar and Facebook messaging is good enough for me. But for those who want to embrace the bleeding edge of technology:

Mingly: Contact management system that notifies you when it’s your friends birthday or if your friends change jobs (and things related to the whole “It’s your friend’s special day”). It allows you to easily set up reminders to touch base with people. The initial set up time was too much for me so I abandoned it. Also, they lock up a lot of premium features for a price.

Boomerang for Gmail: It’s a pretty good software for sending emails at a certain time. You can set a reminder in case your contact doesn’t respond for a certain amount of time.

Newsle: Tells you whenever your friends end up on the news. It’s pretty neat but usually there are about 5 people in your social circle who dominate the news. Usually it ends up being college athletics or some startup your friend founded or something. Still pretty neat when you can congratulate them or if you actually spot them on the news before they do.

Refresh: More for networking. It brings all the information you can find about the person from the web to your Gmail inbox. So you can refer to that witty status your friend posted when you email him. It brings context to conversations, and with context comes relevancy. This is more for networking as well. 

Bonus: Advice for Incoming Freshmen

I’m including this section because I always like giving “Things I Wish I Knew When I Was ___” types of advice. Also since it’s the beginning of the school year, and freshmen are quite conducive to making a large amount of friends in their first couple of weeks, and subsequently, hemorrhaging 80% of them throughout the school year. In bullet point fashion:

  • First off, it’s pretty natural to lose around 40-70% of your friends during your freshman year. If you’re not losing that many friends in college, you’re certainly not making enough of them. The difference between my mistake and this was that I didn’t consciously get to choose who I got to keep, and friendships were therefore subjugated to logistics, like being in the same class or living in the same dorm.

  • The key to college students’ heart (especially upperclassmen) is through dorm food. No college student can not deny free food. Want to meet the president of a club? Offer a meal at a dining common. 90% of the time they will accept, and you’ll get great 1-on-1 time with them.

  • No more cliques. Make friends with individuals, not with collective groups. Groups form from individuals, not the other way around. Here’s an example to illustrate my point: You’re not really friends with everyone in Dodgeball Club just because you joined Dodgeball Club and attend meetings. Group membership is correlative to making friends, but make sure to extend that extra effort to know each individual.

  • Take notes on people when you get their contact information. For example, “James Maa: Talks a lot about computer science. Has a pet rabbit.” It’ll help you remember them better. Put it on your calendar to touch base in a week. Check out Mingly or Refresh if you want the technological infrastructure for this.

  • Introduce friends to friends. Form connections. Be the guy who knows everyone. When you connect everyone, people will connect you too.

  • Everyone says to avoid people who table or flyer, but sometimes it’s pretty nice to say hi to them and talk to them, even if they’re trying to sell you something. You become Mother Teresa relative to all the other people too busy to chat.

  • Stay out of your dorm room for as long as possible. It’s much harder to meet people when you’re indoors. Attend as many events as possible.

  • Misery loves company, so organize lots of study parties, and attend a lot of them too.

  • Please, please make an effort to remember people’s names. Practice often, and be shameless to admit when you forget.

  • Screw jaded upperclassmen. They’re not worth your time.

  • Rejection: It’s painful, but not that painful, so do it.

  • Be a freshmen: I’m a junior now so I don’t get to act super friendly and annoying without cause. You guys are supposed to be overtly friendly and try to make friends with everyone, so act like it to your advantage.

Conclusion: Make Time for Your Friends!

Once again, my past self has led me into the trap that there is little to no balance in life. Social-Sleep-School, choose two.

I used to try to keep myself busy when people didn’t invite me to events. It was more of an immature lashing out through resentment rather than a rational choice to spend Friday nights alone. I would promise myself that while people were out having fun, I would get ahead in life and show them who’s wrong to exclude me. But because it was acted out of resentment and disappointment, I usually wouldn’t get anything done. I would often end up watching TV or surfing the internet because I couldn’t work with all the emotions bottled inside of me.

Looking back, I missed out on a lot of friendships and opportunities because people either assumed I was busy or they thought I didn’t want to hang out with them (they most likely perceived my passive aggressive behavior) and therefore didn’t invited me to their events. Me, being butthurt, would further isolate myself from their social lives.

This vicious cycle was not healthy, and I’m afraid too many people are falling into this trap of holding such a pessimistic view on relationships. It’s natural for people to forget, don’t mistake ignorance for malice.

Then at one point I thought I really was busy. It was no longer resentment that lead me to narrow my social circle, but rather my prioritization of my personal success over my social life. I thought I could work hard now, and earn my friends later. But it doesn’t work that way. Many of my friends didn’t appreciate that I prioritized my own success over our relationship, and many backed down out of an non-reciprocal relationship in which all I wanted the companionship and support of the friend without offering anything in return. People were right to leave me, I was a poisonous person at one point.

I’m making a change, and so should you. Make time for your friends! You have to eat, don’t you? Well, so do they! Eat lunch with your friends! Exercise with your friends, do homework with your friends. Set something up, be in each others’ presences. It doesn’t take a lot of time or energy to maintain a relationship, and speaking from a strictly selfish perspective, there is so much to gain from your friendships! You will learn so much from your peers, you will gain so many contacts, and in general your life will be so much happier and exciting when you can actually have shared experiences!

Right now is not the time to put aside friendships for your own success, because success cannot be achieved without friends helping you along the way. Think about this interesting fact about the college and high school environment: Right now will probably be the only time where the environment is setup for you to make and keep friends. You are all placed in a geographically close area, forced to interact with each other, and share a common interest and age group. It will be hard to find such an environment so conducive to friendship at any other time or place in your life. Cherish your opportunities! Cherish your friends! Cherish your friends!

The Best of Luck to All of You!

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8 Responses

  1. Jon says:

    I found this on reddit, and I think it’s really insightful! You’re saying a lot of things that I had to figure out for myself, and some things I hadn’t thought about too. It’s good to see it all laid out logically like this. Thanks!

  2. nick huffman says:


  3. Mimi says:

    This is a really great article. James Maa, you’re a great person, and I love how you took the time to write out this article and help people, or just to help by giving advice. I really like that. Keep up the good work!

  4. Saiham Sharif says:

    thanks for writing this out! i’m leaving for a college in a few days and i’m glad i read this.

  5. Anonymous says:

    I absolutely love this guide, thank you so much for spending the time to do this! I’ve honestly never found social advice that resonated with me like this before.

  6. Anonymous says:

    If only I had real life friends and If only I didn’t have anxiety, this sounds like it would be a great guide.

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