Ahoy, Captain!

I (she/her) have lived in a new city for three years, and have made no friends. Or, rather, no outside-of-work friends. I work in a wonderful place with the loveliest people I ever expect to meet, but that delightful cameraderie hasn’t translated to IRL hangouts– for me, at least. It’s the kind of place where two coworkers will go on a weeklong trip abroad together.

Making friends has never come easy to me. I live alone, I travel alone, I don’t really go out, and when I do, it’s always by myself. Most of the time, I’m okay with it, but after three years… it’s like, okay, let’s get someone else in here.

I’m part of an occasional trio (like, we gave ourselves a name and everything) with two other coworkers, “Patrick” (he/him) and “Tess” (she/her), who I’d like to become actual real life friends with. They’re both about three years older than me and are closer to each other than they are to me– they’ll occasionally have lunch with just the two of them, at least one Sunday brunch, and Tess will hang out at Patrick’s desk (which I used to share with him; that’s how we all got close). It stings a little to be excluded, but we still get on really well when we’re together.

How can I ask them if they want to be friends with me outside of work, when I’m still unsure whether they genuinely want me around or whether they think of me as the pudgy, weird little sister?

Thanks a million,

The Lost Musketeer

Dear Lost Musketeer,

You can’t turn work friends into real friends by asking with just the right words, but there is a way to find out if a work friendship can flourish outside of work: Invite your work friends to do specific fun things with you outside of work every now and then and see how it goes.

Not “would you like to be my friend” (too much pressure) or “would you like to hang outside of work sometime*?” but “I want to go the new [art exhibit][movie][free concert][craft fair][try out this new board game][go see this author read][play Pokémons] after work on Thursday night, want to join me?”

A review of low-pressure invitations for beginners:

Pick something low-cost, low stakes, and logistically easy.

Choose something you would enjoy enough to do anyway by yourself (vs. trying to suss out the other person’s exact niche interests and cater to that).

For coworkers, after-work plans are a good place to start. Sometimes people have to rush home to walk the dog (or are otherwise Done For The Day), so don’t take it personally if that doesn’t work all the time for everyone, but sometimes adding an hour onto a thing you already have to do is easier to agree to than the prospect of scheduling a weekend day.

*Suggest a specific day and time and activity right from the start when you make the invite , because: Are you inviting people to Do A Fun Thing Together or are you inviting them to a group project called Let’s Possibly Work On Making Some Plans Someday, those are not the same things at all. The ambiguous “sometime” invitation is the worst for anxious people because when the other person says yes to “sometime” but then makes no moves to make a plan, you have to ask them again to make the actual plan and start the whole waiting/rejection cycle over again. You’re the one who wanted to Do Stuff, so do the work of suggesting some specific Stuff. Specifics make it easy to say “yes” or “no” to whatever it is and make an alternate “I really want to hang out with you but not Thursday, is Wednesday possible?” plan.

, because: Divide and conquer. If your “trio” hasn’t become an outside-of-work trio in three years, maybe don’t start there. Instead, think about inviting just Tess or just Patrick to something the first few times vs. keeping “the trio” together. It’s okay for them to hang out with each other and not invite you (it’s not something they’re doing at you), it’s also okay for you to develop friendships with them that are different from the vibe you all have together.

you), it’s also okay for you to develop friendships with them that are different from the vibe you all have together. Take your time, go slow, don’t put pressure on anybody (incl. yourself) for a certain outcome. If someone wants to keep a solid, enjoyable work friendship as just a work friendship, it doesn’t mean they don’t genuinely like you or automatically mean that they see you as a “weird pudgy little sister.” Not everybody crosses the streams, not everybody crosses the streams with everybody else, so resist the urge to strategize too much or obsess.

That’s it. The only way to know if someone you like will want to hang out outside of work sometime is to ask them to do stuff. Do they say yes? Do they seem glad you asked? When you ask do they say stuff like, “I’m so glad you asked!” or does it get weird and quiet or do they suddenly become a font of elaborate excuses?

Do they actually show up when they say yes? Is it fun when they do? If they can’t hang when you suggest something, do they suggest alternate plans, do they invite you to things sometimes, too, and make it easy to hang out? Does it feel natural and easy and fun to hang out with them outside of work the way it does at work? Do you feel good and relaxed and happy around them? If so, great. That’s a start.

Try inviting them once or twice and then, if it doesn’t happen or the response isn’t favorable, stop. If you feel like you’re doing a lot of work but receiving no reciprocity, stop. If you’re having trouble taking “no” for an answer, stop. If anything about what’s happening is not making you feel good, stop. And – this is key – if they say no to an invitation or if an outside-of-work friendship with Tess and Patrick doesn’t seem likely to happen in general, BE COOL. Specifically, continue being pleasant and friendly and easy to work with when you’re at work, show them you can take “no” for an answer and that you aren’t going to pressure them about it or make it difficult, show them that you still like them as coworkers, and do your best not to take it personally. Three years of having cool, friendly coworkers who aren’t outside-of-work friends isn’t a punishment or a failure if it doesn’t morph into something closer.

I include this warning because there are some things in your letter that give me pause, specifically where you say “it stings a little to be excluded” when Tess and Patrick hang out by each other’s desks and have lunch together or note that they’d had “at least one Sunday brunch.” You are obviously much more invested in Tess and Patrick than they are in you, which makes this project of trying to “turn work friends into real friends” automatically risky. But two work friends are hanging out together when they feel like it isn’t “excluding” you, it has nothing to do with you either way, and you wouldn’t be “excluding them” if you did the same with either of them or other coworkers. Patrick and Tess don’t know they are your only friends (or the closest thing you’ve got), that’s not on them, and “the trio” can have duos inside it without hurting anyone or being unfair. Monitoring their friendship and time together (and seeing it as something that probably “should” include you all the time instead of just some of the time and something that hurts when it doesn’t) is not going to be a good basis to build on. So for best results, I want you to resist this framing and habit with everything you’ve got. Pressure and obligation are the enemies of affection, you do not want to add those things into a what is now a pleasant work friendship.

Additionally, you didn’t ask for general making friends advice but I’m recommending some anyway. If you want to have a richer social life and form new habits around making friends, there are many things you can do and control that don’t depend at all on Tess and Patrick. This has bearing on the problem of wanting to become closer friends with them, specifically, because the less pressure you put on yourself to make something happen with them the easier time you’ll have being chill and open to whatever happens. If they remain your only/best options, everything you do to connect with them is going to have higher stakes than it would if they were just one part of your social life. Working on expanding your social life in general is going to give you a richer field of options and take pressure off any one person to sustain you.

You can still take advantage of the social culture of your workplace in a way that doesn’t put pressure on Tess and Patrick. For example:

Make a point of showing up to work parties and casual after-work or outside events arranged by other coworkers when you are invited. You may already do this, but sometimes I get letters from people who have stopped getting invited places but also never go when they are invited or stopped going when they used to be invited so it’s easy for organizers to assume they don’t want to come. If you’re in one of those impasses, break it!

Make a point of getting to know the most outgoing and social people in your office. Who is driving that camaraderie that’s so great?

Invite nice coworkers – beyond Tess & Patrick, and think widely in terms of age – to lunch every now and then or to do the odd weekend or after hours thing. You don’t have to wait to be invited, and you don’t have to agree to lifelong friendship or give someone a kidney to eat a sandwich with somebody for 30 minutes or grab a drink after work now and again and get to know them a little bit better. You don’t sound to me like someone who is in the habit of seeking out company, which definitely is an okay way to be, but you have a safe, friendly lab to practice in and you’ve indicated that you’d like more company, so use what you’ve got!

If a particular coworker generally does a lot of work organizing fun events, say thank you. “I appreciate you putting this together, I had fun, thank you.”

Offer to help next time they’re arranging something. Move chairs around sometimes. Hang decorations. Make the grocery store run. Be the person who suggests the new lunch spot or bar to try.

Be one of the people who welcomes in new people, shows them around, gets to know them, and trains them on work projects. You know what it’s like to be new in town and new to the company, I bet you have a lot to offer, so pay it forward.

Outside of work, it’s time to try the stuff we write about in all the posts about making friends:

Please know, you’re not alone in being more alone than you want to be and wanting to do something about that. There are other adults who want to make new friends and who aren’t sure where to start, this is a skill we all acquire at different paces and one that we have to revisit and relearn over and over again in life. Being lonely doesn’t mean there’s something wrong with you, it’s not a life sentence, the further we get from our school years and being grouped by age, the harder it all gets. Take heart.

You aren’t alone in wanting to meet new people and make friends specifically in the town where you live right now. It’s Friday today. Chances are there are some lovely nerds in your city optimistically setting board games out on cafe tables, hanging art on gallery walls and putting out plates of charmingly cubed cheese, putting finishing touches on this week’s bar trivia questions, setting up the sound system for the comedy open mic, finalizing the “will call” list for the theater performance, wondering if they’ll ever find a rogue for their D&D game, collecting donations at the food pantry, and working to get candidates on the ballot or write postcards to voters right now while I’m writing this. Just because you haven’t branched out and found these social outlets yet doesn’t mean it always has to be like that. There is Stuff To Do, waiting for you to show up and do it, chances are you won’t have to invent it from scratch.

For best results find a hobby group, class, MeetUp, sport, church, choir, community theater company, social dance class, improv troupe, volunteer organization, etc. that interests you. Something you’ve always wanted to try, something that sounds neat. Something that meets once a week and is open to all.

Assuming nothing terrible happens and it’s not immediately full of assholes the first time you go, go back at least three or four times before you make a decision about whether it’s really for you. If you’re slow to warm up to people, think of it as giving yourself the gift of some time to come to a simmer (and vice versa, since you’re probably not the only shy person or person who is out of the habit of connecting).

Find the most outgoing people at the events you do go to. The kind of extroverts who go to the trouble of setting up hobby groups LIKE meeting new folks and LIKE introducing them to each other, you’re not bothering anyone by asking them to introduce you or show you the ropes. Appreciate your local extroverts!

As with work events, thank the organizers. If you can, offer to help in a way that’s easy and sustainable for you.

Don’t give yourself the goal of “make friends.” It’s too much too soon. Give yourself goals like, “meet three people and learn their names.” Pay attention to who makes you feel good, who you like. Don’t worry so much about being liked – Patrick and Tess like you, so chances are other people will grow to like you too if they get to know you a little bit. The reasons people like you are part of you, even when your current favorite people aren’t around.

Small Talk will happen, might as well get good at asking and answering a few basic questions about what you like doing and what other people like doing. In my opinion you have an excellent Small Talk For Meeting New People story: “I moved here three years ago but it’s like I’m brand new, since I spend most of my time working and I haven’t gotten to know the place yet. These days I’m trying to leave work at work and get out more, so I’m asking everyone I meet to tell me good spots to hang out.” “I moved here three years ago and I met so many great people at work it was easy to not have to work very hard at making friends, but now that I’m settled I’m trying to branch out more. Where would you send somebody who just moved to town that’s great for meeting new people?” You could ask your most social coworkers this, too, like, “Hey, everyone here is so friendly and cool, when I was new in town it was so easy to just look to this place for people to hang out with, but I’m really trying to get out more this year. Where would you send someone who was brand new in town and trying to make new friends?”

See also: “What are you nerdy about these days?” “What’s your favorite place around here to show off to visitors and new people?” “When you first moved here how long did it take you to feel like it was home?” “You didn’t grow up here? When you moved, what was the best thing you did that helped make new friends and be a part of the community?” “I really want to learn how to ________. Know anybody who teaches that/groups for beginners?”

When people you meet do invite you to more stuff, start saying “yes” and showing up instead of defaulting to doing things alone. Even if the hosts aren’t best friend material, they may know your “best friend” material, for example I met Commander Logic at a Halloween Party where we’d both been somewhat dragged away from being in the middle of the same much-anticipated book. There’s no substitute sometimes for showing up. If whatever it is is not your scene, eat a snack, say some pleasantries, thank the person for inviting you, and go home. Give yourself victory points and a treat for making the effort, trust that Netflix will still be there for you in an hour. Try again another time.

When you start to click with someone at the group things, invite them to hang out solo and see how it goes.

Use social media…socially. To follow up with people you meet and like, to RSVP to events, to get to know people in a casual, ongoing way that requires little effort.

Pace yourself, be nice to yourself, pay attention to your own pleasure and comfort levels, and give yourself lots of time and chances. You’re doing a hard thing, so don’t be hard on yourself.

I hope you get what you want from all of this and I’m wishing you a more social 2020 both at work and away from it.