#259: Do you feel “chosen” by your friends?
On friendship in your thirties (and beyond)
Morning!
Today I’ll be answering a question and teeing up a discussion on friendship in your thirties. When I was writing in my twenties, I found myself fielding questions and covering the topic of friendship all the time—it’s very much in the air at that age. But I’ve actually found that managing friendships in my thirties has been just as rich, surprising, and challenging, only with slightly different points of focus, and potentially fewer scripts. The below question I received spoke to me for a few reasons, so I wanted to use it today as topical inspiration:
“I’m in my mid 30s and I’ve never had a best friend—never been someone’s automatic first call, their person. I’ve done a lot of work on myself and I have real friendships now, but I still never feel chosen. I watch my friends prioritize each other and I’m always on the outside looking in. Is this something that can change, or is there a point where you have to accept this is just who you are?
I’ve always had big friend groups that shifted with different seasons of my life, but I’ve never had a person. I had a codependent relationship with an ex where we both desperately wanted that best-friend dynamic, and he became everything to me, which ended badly. Since then I’ve done real work on myself: therapy, dropping the ‘cool girl’ act, finding people who actually match my energy. I have genuinely close friendships now. But I still never feel chosen. I watch my friends make plans without me, and it stings in a way I can’t shake.
Is this something that can change, or do some people just never become someone’s person?”
I’m so sorry you’re feeling this way. While my own hangups take a different shape, I relate to many of the sentiments you shared here! If my years thinking about this topic have taught me anything, it’s that everyone has a friend hangup of some kind.
As someone who’s historically been very best-friend-oriented and only now feels slightly more group-oriented, it’s been fascinating for me to experience the upsides and downsides of both. I can’t tell you how often I felt inadequate for not having a consistent “crew” as a younger person—I assumed people who had one were somehow more lovable or higher functioning than I was. I had a similar insecurity about the fact that I hadn’t done a good job of staying close with old friends, and had a way of “resetting” according to my geographical environment, which is another habit I’ve since broken and see differently now. The overarching lesson has been that different friendship formats are suitable for different personalities at different times and in different circumstances. There isn’t one ideal setup, and more importantly, it’s impossible to reap the benefits from every setup at the same time. There are always trade-offs.
Years ago, a friend told me she envied how many new friends I’d made in my late twenties. To me, her connections felt so old and steeped in tradition, like she had an entire network she’d grown up with, a family. It made me feel flighty in comparison. I told her I’d always admired her deep connections, and she explained that while she did value her old friendships, she also felt a bit stagnated by them, stuck in her childhood self. She admired how I’d reinvented, and thought my social world reflected that back at me. It was a transformative moment for both of us, to recognize that both of our circumstances came with challenges but also had benefitted us in ways we didn’t always appreciate.
In your question, you mention a lot of friendship achievements: You’ve fostered big friend groups throughout your life (I’m impressed by this!), you’ve let them shift with the seasons, you’ve explored the topic in therapy, you’ve committed to being authentic and finding authentic connections, and now have genuinely close friendships that feel “real.” I’m not just hyping you up, these are signs that you are socially high functioning. Many people are trying to develop the skills you’ve both exhibited naturally and also learned to put in practice. Your longing is no less valid for it, but I do think you should feel proud.
A few ideas passed through my head while considering your predicament. The first was triggered by your mention of codependence. Although I felt envious of big friend groups as a younger person, I was obsessed with having a best friend. This was not always healthy. I was after the exact relationship you described: being someone’s automatic first call, their everything, and vice versa. Only later did this occur to me as pathological, an expression of my fear of being left out or behind. I only felt safe if I could claim a best friend and also hold the title, anything less felt risky. Today I find myself much more resistant to this idea: It’s not always healthy or realistic to winnow your energies that way, or expect it of someone else. In the same way it can be harmful to a romantic relationship to expect them to be everything, the same can be true of friendships. When I find myself overly eager to designate someone a best friend, I now recognize that impulse as fear-based.
One of the ways this lesson has more materially manifested for me is learning to let go when I feel left out. Obviously there are limits to this—exclusion can be cruel in some circumstances—but as I get older, I’ve really tried to set down the calculator. I’m not saying I never get a stomach ache upon hearing of friends doing something that I might have expected the invite for (or an extension of this: the dreaded group chat without you!), but I’ve gotten the pains down to a cool five minutes. The pep talk is always the same: Unless I doubt the genuine affection and care of these friends, it’s no big deal. Sometimes plans come together when you’re not around, sometimes they cohere around an experience or quality you don’t share, sometimes people have history together and want to revel in that, or any number of harmless reasons they might hang out without you. This is not an indictment of you. The golden rule applies: Sometimes you want to hang out with certain friends without everyone you mutually love being there, and it’s not meant as a slight.
Before I move on to more actionable ideas, I also want to talk a bit about social roles in friendship. Something I’m regularly making (and remaking) peace with is that I’m more likely to be the planner/inviter than the invitee. It sounds like you may fall in the same camp. This role comes with so many (I’ll say it!) admirable strengths, but carries risks of feeling unwanted and small. When I was younger, and sometimes even now, nothing seemed a surer sign that you were loved and liked than being invited to lots of things. But I’ll never forget when a friend of mine who embodied that quality said that they felt the opposite—my role as the planner, they said, radiated confidence and self-respect. They felt nervous initiating social plans, and this made them feel small. Every social role has their cross to bear.
So far this answer has focused on letting go, but I do want to give space to the possibility that this desire of yours is not pathological or capable of being resolved intellectually. Maybe it feels grounded and instructive regarding how you ought to prioritize right now. If you’ve historically been wired to be part of a friend group versus fostering deeper one-on-one relationships, there might be a few things you could do differently to encourage more depth. Apologies in advance if these are obvious, but my best tips off the top:
1) Spend time together that’s unstructured. Not just coffees or dinners planned three weeks in advance, but ambling around for an afternoon, running errands, keeping each other company while you clean out your closet, etc. Drop-bys are a big part of this IMO—going to something near their apartment? Ask to stop by beforehand to say hi!
2) Tell them your secrets. Being overly private is anyone’s right, but I do think it inhibits the development of super deep connective tissue. Hear and keep their secrets too.
3) Ask for and offer favors. This one can be really tough, but you’ll know you’ve broken through when they lean on you in a pinch. I never forgot my friend’s advice to always help your friends move: Not only is it a kindness, but it’s very bonding to do something difficult and sweaty together (then revel in it afterwards).
4) Communicate informally and spontaneously. FaceTime when you’re bored, or after they’ve had a big night to ask how it went. Text them things that remind you of them. (Obviously don’t continue if these don’t feel natural and aren’t being enthusiastically received.)
5) Be willing to be a mess in front of them (literally, emotionally), and receive them in kind. My friend Gyan1 has a great bit of advice about not cleaning up too much before your friend comes over. I don’t always follow this, but I try to keep the spirit in mind: If you want to be known, let yourself be seen.
6) Make the plans happen that you want to happen. You can wish that someone else had the idea or took the initiative, but there’s no use wasting energy wishing someone else did something you’re just as capable of. So plan the trip or the weekend or the class. Build the friendships you want to have.
With the right person, a lot of this will click. With someone more suited to a different role in your life, it might not. I say that because sometimes the right person just hasn’t come along yet. I’ve been really surprised by how many friends I’ve made in my thirties, when I expected those to primarily take root in my twenties. But those friendships also look different than I might have expected. Whereas some have immediately struck me as a “best friend,” I find myself way less fixated on this designation, and a lot more appreciative of more idiosyncratic styles of friends. “Best” isn’t everything, nor necessarily sustainable. The longer I’m around and the more life shifts I’ve been privy to—in myself and in others—the more open I’ve become to the logic of reasons and seasons. I used to see friendship as this sort of linear project, and now I understand it much more cyclically. There are winters, springs, summers, falls. They all serve their purpose.
I hope that, whatever you might take away from this, you give yourself credit for what you’ve built. As inundated as we all are with cultural models for what a fulfilling social life looks like, I think it’s imperative that we pause and take stock of what we do have—not in comparison to other people or some ideal we’ve seen in movies—but in the vacuum of our personal lives. Maybe you really do want a best friend, or maybe you’ve just been led to believe you were faulty for not having one. Regardless, remember there are no friendship boxes to check. Even if there were, they wouldn’t stay checked for long. Friendship is an evolving organism—impossible to pin down, and all the better for it.
I’d love to hear about your experience with friendship in your thirties. I didn’t fit this into the above, but I think having a kid has brought up a lot regarding friendship for me: the distance I feel from old friends without kids, the distance I feel from new mom friends with whom I don’t share history, but also the joys of going through this transformative experience with both groups. There’s a lot there! I’m really interested in the way our big life choices impact friend dynamics at this age. In your twenties so many friendships feel solid and impermeable, or else flighty and unreliable, only to be totally inverted by life changes. It’s fascinating. If you have thoughts for the questioner or general thoughts on friendship as you age, please share. I’ve opened up the comments to everyone:
Last Friday’s 15 things, including five pieces on Iran. ROTW was how to get fiber—STUNNED BY THIS RESPONSE BTW. So many fiber warriors in my comments?! I learned so much. Podcast on Wednesday was a Voice Note on a quote I read last week that got stuck in my head and made me think differently about an internal struggle.
I’ll see you on Wednesday for Dear Danny!
Haley
Gyan actually wrote a book on friendship! Friendship First, by Gyan Yankovich.



Excellent recommendations and post. I am in my mid 40s and used many of these tips to find great adult friends who had more time for friendship (I dont have children, so my kid friends while great, just didnt have the bandwidth).
I second, you can do all these things and the friend just doesnt click. Keep moving. Don't try to make a stiff connection work. Your people will be glaringly obvious when you find them.
pls do a voice note with gyan! eager for more on this topic; both the evolution of friendships as we age and something I’m desperate for more models of: conflict with friends!
I’ve had a hard time in my early 30s as close friends begin to have kids. despite many offers of practical support and a whole lot of flexibility, I feel auto de-prioritized compared to the ease of being with bio family. *i think* so much of it is caught up in the ability to feel messy, vulnerable. it’s been, at times, heartbreaking & yet impossible to not feel irrational given how much their lives have shifted.
I really loved the book “radical intimacy” Sophie K. Rosa for wisdom and critiques of how capitalism has shaped the nuclear family and the domestic sphere to keep us isolated from one another. would love love to deepen this with convos and any recommended texts!