Ask Alex: How to make friends and… That’s it.

Hi there Alex!

What are the best ways for post-college young adults to make friends in a new city? I moved to Portland about 3 years ago for a job. I’ve joined some clubs, tried online dating, taken a few classes, and attended just about any event that has piqued my interest since I moved here.Still, I am struggling to find a friend I can call up on a random Tuesday night and meet up for dinner or drinks. It’s incredibly frustrating. I know part of it is because at this point in my life (late 20s) people are pairing up at an incredible rate and focusing on starting families, however I can not be the only single person in my age group in this city. As pessimistic as it sounds, it feels like everyone has their group of friends set already and inviting a new person into that group isn’t a priority. Where are all the late-20/early-30-year-olds who want new friends hanging out?

I cannot be the only person in this city who is in this position! What do I do? I feel like I’ve tried everything! I’m beginning to feel desperate!

Lonely in Portland

This is such a great question, thank you. You not the only person in this position; as you will see, this is an issue that many have struggled with and put a plenitude of thought into. Thinking on this has made me consider my own approaches to meeting people and making and maintaining friendships for the first time in a very long time and so I appreciate your giving me the opportunity to do so. Because of this, I was equally curious to see how others would approach this conundrum and so I posted an iteration of the question to my Facebook wall to get insight from the community there. Over 40 people offered their experiences, ideas, methods and insights.

It sounds like you are pretty good at getting in front of people. This is a great start. I used to be incredibly good at this, but as I have gotten older, it has been more difficult for a number of reasons. Before any event, I go through the following nerve-racking exercise:

•    In the first half hour: Profuse sweating. Nervous belly. Hide in bathroom to get a grip on hyperventilation.
•    After I come down: Oh, this is actually pretty cool. This person is great. Oh! So and so is up to this! Neat! Why don’t I talk to these people / come to this place more often?

Beyond my emergent social anxiety, I have had a lot of luck with meeting folks through going to events and helping to organize them as well. My most recent solid friendship came from a board position I had with Portland Greendrinks, and it took said friend and I a couple of years of knowing each other before we turned a passive friendship into something more by collectively putting forth more effort. The part of friendship I tend to be bad at is follow-through. I am great at meeting and engaging people a couple of times, but I can be disorganized and aloof and so being sure to reach out as much as I expect to be reached out to—or being as inviting as I would like people to be to me—has proven to be a hurdle in the past. I have gotten better at this over time, and have certainly sparked new friendships as a result. I have also revitalized some friendships that had, for one reason or another, become anemic over the past handful of years.

Further, in approaching friendship cultivation, it is important to be honest with yourself about what you are looking for in a friend, and about what you are able to bring to the table. Understanding what you are looking for and what you have to offer can make easier the process of deciding upon which acquaintances you are willing to turn into friendships. As my wife has said of making friends, “If you are looking for someone to text back and forth with, I am not your girl. If you are looking for someone who would bail you out of jail at two in the morning, let’s hang out.” This knowledge has helped her to better understand who to pursue as friends and who to continue considering friendly acquaintances.

It is also worth mentioning that, coupled or single, it can just be difficult to make friends these days. We are all incredibly busy, and expectations to be working all the time—even when we are not at the work place—are certainly intensifying. Further, and maybe because of this in part, there has been a rise of passive acquaintanceship due to ambient social media familiarity. In other words, we think we know someone, or have an idea of what is going on in the lives of those in our networks, but we don’t necessarily proceed with taking these connections to the next level.

Finally, the following responses address the question more generally, and while they might not be helpful for your particular conundrum, they could be helpful for onlookers. They are largely about meeting people, but there are also a good deal of insights on pursuing and maintaining friendships. This sort of crowd-sourced raw data dump is not one I will frequently employ, but I found it appropriate to answer this question as thoroughly as possible by way reaching out to a community of friends (and friends of friends).


Note: SO MANY THANKS to everyone who weighed in!


Kate: I don’t think it’s because of pairing up, it’s because we’re all just so damn busy trying to keep up.

Jenny: Few aspects to this, forgive the paragraphs. Sounds like this person wants to break into a ‘group’ of friends. Busting into a clique is hard, and maintaining that dynamic once in is harder. Maybe they should focus on cultivating a few (or several) individual friendships instead, and accept that the intensity of friendships changes in adulthood. Everyone is juggling families, jobs (or trying to find jobs), and we all have to be a lot more flexible with scheduling. Who I get to hang out with now morphs and I just roll with it. That said, they need to initiate and follow through to make a connection happen. If you meet someone cool, and you say, we should do coffee, then follow up and make coffee happen. S/he should evaluate if they’re an introvert or an extrovert. Introverts do better with one-on-one friendship activities (coffee, a film) vs. parties, pot lucks, athletics. If they are an introvert & are forcing themselves to go to parties and networking that way, they may not be their best self in those situations, impeding their intent to make friends. More thoughts, based on, “Still, I am struggling to find a friend I can call up on a random Tuesday night and meet up for dinner or drinks.” This being Portland, where many are struggling w/cash flow, meeting up for dinner/drinks becomes a bit tricky. (I can’t afford to go out to dinner.) It’s hard for close friends to admit times are tough, much less to a new person. That said, plenty of foodies are navigating these times; maybe join a foodie group? Or pitch a lower-cost activity to new acquaintances, in case it’s the money thing in the way: for example, The Nick has $5 films on Tuesdays. Voila, Tuesday fun, without the awkward money talk. More: venture outside your peer group. Welcome younger & older acquaintances.

Elise: It is also important to remember that meaningful friendships take time and effort. One cannot assume they will just be absorbed into the group. Ask for her number, find him on Facebook. Ask if the person wants to go see this movie. You have to be willing to work for it. You know, without being an overbearing stalker.

Emer: As someone in a similar position, I can attest to how challenging it is to make friends in a new place—let alone Maine. I grew up in NY state, where people are initially hostile, but warm up and invite you into their circle within minute—whereas in Maine, people are really nice initially, but it takes years to get invited to inner circle events.

Marya: I’m not single, but since my husband and I moved here we’ve both made friends. Some haven’t “stuck” but it is always worth a try. You do have to put some efforts in and roll the dice a bit. Sometimes you’ll hang out with someone a few times, or even longer, and it just won’t end up working, but then sometimes the opposite will occur.

Thomas: Strangely enough, I sorta feel like the large influx of (mostly young-ish) people “from away” to Portland over the last decade (which is GREAT) may contribute to this wariness to the extent it actually exists. Maybe people think everyone here is a die-hahd Mainah and is less likely to interact as a result. One thing about being involved with Greendrinks I’ve realized is there are a LOT of young people in Portland who are not local by birth who are out there trying to meet people and trying to make it work from a career perspective at the same time.

Jessie: I’m 30 and friends I made in my 20s when I moved here have sorta moved away leaving me to fend for myself, I am horrifically introverted with a strong desire to be social with low-maintenance besties. I met a couple like-minded individuals through events, stalking on Facebook and twitter, and friends of friends. Drinking helps, for both being social and the loneliness. Meeting people is easy. Maintaining friendships when you have weeks and weeks of anti-social fall-off-the-earth probably-haven’t-showered-in-days bout…

Michael: It seems to come down to different strokes, for different folks. Everyone has their own unique scale of sociability, life experiences, and frankly wants and desires. How to build relationships that are, for lack of a better term, mutually beneficial is tricky. It’s hard to find a tailor made fit, in an off the rack world In essence who we get along with and what might be a fulfilling friendship is quite finite. (Yeah you can have a host of “drinkin buddies” and/or acquaintances that for most of us turn out to be a bit of fun but ultimately fickle, and shallow) I’m lucky, it’s been easy for me in Portland built primarily around the music scene and some great new friends in that space and the “network” just kinda grew with off shoots in the media and professional world, business owners and the movers and shakers in this kooky town. Being a Boston transplant the biggest takeaway is Portland kinda requires a more gentle, organic pace if you will. Most folks have no effs to give regarding what you did, or who you did or how many trophies you have from “away”. Which is kinda cool. But it’s been a pretty consistent growth of friends but that’s over almost six years. Maybe Portlanders are a bit wary? Lastly I think most people are looking for that special someone or to couple up if you will. If you’re fortunate you find that someone, and then other challenges come up with how to enjoy a new relationship to the fullest while still nurturing and cultivating friends — who are also coupled up or looking to do so. Advice? Take it easy. Drag your ass out, and explore something new every week. HELP OUT! There’s a TON of events and groups and goings on that are always looking for new energy and help.


Esther: I joined in my new city! I went to one event, it was really great! Gotta get to another one.

Jenny: Way back in the day, I placed an ad for friends in the Casco Bay Weekly, and made one of my life friends that way. Never hurts to ask for what you want.

Nikki: Join an event that requires you to talk and share some personal information. This will help get the ball rolling and break the ice. Ive been to a few events where someone has said one thing that’s stuck and lead to a great conversation.

Scott: Start issuing invitations instead of waiting for them. Dinner parties are great because you can throw together people who don’t know each other already and then everyone is in the position of getting to know each other. When I lived in Portland I did a dinner party every Friday evening for years. There were a handful of regulars and then I’d invite any interesting people I met along the way in life, usually at my favorite coffee shop (Green Mountain) or other places where I’d run into new people. Several of my favorite people in the world went from coffee shop acquaintances to close friends by this method.

Bernadette: I struggled with this big time when I moved to Nashville. Finally, I found a running club that goes to the bar (and is generally social with one another outside of running) that is where I found the bulk of my close friends. Seems kind of silly, I know, but I kind of can’t imagine what would have happened had I not headed out one day…or without my Wednesday 2-for-1 beers.

Seren: Talk to strangers. I made friends with my chiropractor’s receptionist because I thought her jewelry was awesome! now Shane is one of my good friends!

Diana: Be friendly with the restaurant workers, bartenders, and baristas you meet! Frequent the local music scene, go to events solo, and don’t be a wallflower! Join one of the many yoga studios in town! Portland is the friendliest town I know, I make new friends here on a weekly basis, and I’m well into my 30s. Just be open to experiences and conversations, and it will all fall into place! Also: if you’re shy, but bold enough to reach out, maybe a re-channeling of that moment of boldness would help! Deep breath. “Hello, how’s your day? Heyyyy, I just moved here, what’s fun this week?”

Emer: I’ve found success in finding something you’re passionate about, becoming a regular at the places that host your passion, and engaging in friendly light-hearted banter. Also useful: find that one friend who can introduce you to their friends and let it snowball from there. Mario seconds this method: I’d point out this really important sociological paper (hear me out) called “The Strength of Weak Ties” by Mark Granovetter. He laid out the evidence for why “weak” connections with people are in some ways more beneficial to the subject than “strong” connections. His paper was about career opportunities, but it extrapolates to personal relationships too. Basically, the idea is that the best way to meet new people and find yourself in new situations is to look to people who aren’t your close friends, but acquaintances. Since these are people who aren’t totally integrated into your life, they’ll provide more opportunities to meet new folks who may become your new friends. It’s worked for me really well since moving into a city where I didn’t know many people or have any really close friends.

Emer again: Oddly enough (or not), I’ve made a fair number of friends of off OKCupid when I was dating—but also looking for cool people to have conversations with. But mostly—you need to have the chutzpah to strike up a conversation with random strangers.

Elise: I’ve made several friends through eating dinner alone at my neighborhood pub and not being afraid to chat up the strangers around me. Knitting in public also helps to draw people to you. Maybe you don’t knit; maybe you yo-yo, or do card tricks. Bring your joy out into the world and people will be drawn to it, especially in this town.

Susan: ASK! Everybody needs more love & we ALL “deserve it” — remember that there are so many people who would love to be with you. Invite them into your life.

Stephen: I think part of it is initiative. You can attend as many events as you like, but it takes wedging yourself into a conversation and finding a way to connect. I think the early days of Greendrinks, it was easier to do this.


Diana: The Public market house offers lots of interaction, and might I also suggest Newbury Comics or Bull Moose.

Sarah: I used to go sit at a bar after work to read the newspaper and do the crossword. Easy to engage other people and worst case scenario — a glass of wine and a newspaper are never a bad thing

Ashley: Slam poetry, art classes, political activism in groups you believe in, writing groups? Places where you meet people don’t have to be forced—just do things you like and enjoy the like minded people you meet along the way.

Michael half-jokes: AA… the only requirement is a desire to stop drinking. Half this town is in recovery, and the other half outta be.

Sarah: Tandem Coffee Roasters is good because No WIFI, small cafe space, and strangers actually talk to one another and the baristas instead of reading/working. One of my friends met her new boyfriend there!

Susan: A lot of powerful love & friendship connections came out of the League of Pissed Off Voters, Green Party activism, queer activism, immigration activism, Lucid Stage, Portland Lesbian Coffee House meetup… Common purpose, values, playful soul-satisfying fun, all of that will lead you to deep & fabulous connections. For some it could be rod ‘n’ gun club, knitting group, yoga, disc golf… “Life’s a banquet & most poor suckers are starving to death!” — Auntie Mame

Lauren [from Washington, DC]: I don’t know if Portland has gone through the kickball phase the way DC has, but I would venture to say that is the number one way people in their early 20’s meet in DC. There’s something about playing a childhood game, followed immediately by day drinking that gets people friendly with one another. I was on a team for one season about 6 years ago, and I still talk to a lot of the people I met on that team. To which Elise responds: Dodgeball is big here! (Actually, lots of fun sports through Casco Bay Sports) And, if anyone would like to join a Tuesday night dodgeball team, send me a PM … The Jolly Dodgers need a couple of folks for this season. Stephen: Speaking of kickball, PortSports Social Club is a great place to meet people (and partly responsible for my marriage). Megan, Stephen’s wife, seconds Stephen: PortSports is AWESOME for making new friends – not just sports, either, lots of fun events like camping and dancing and drinking! And Carlin adds: I second the idea of the social sports scene! Even if you aren’t particularly athletic, the competition isn’t rigorous and there are fringe perks (excuses to drink). PortSports does pub crawls, trips to concerts and pro games. Also Bayside Bowl will mingle you with Greater Portland’s finest, and Portland Ultimate Summer League is 500 amazing people playing the best game on the planet.

Alex Steed

About Alex Steed

Alex Steed has written about and engaged in politics since he was an insufferable teenager. He has run for the Statehouse and produced a successful web series. He now runs a content firm called Knack Factory with two guys who are a lot more talented than himself.