How do you make friends in the modern world? (A question from Portland, Maine)

The view is not bad either. I cannot complain about the view!

The view is not bad. I cannot complain about the view!

“It just feels a little… raw

A new friend had just asked me why I wasn’t writing about my struggles to make connections in Maine. The only answer I could come up with was that — despite proclaiming that I write what I want to write, and tell the truth as it is, and try to keep it real — it was feeling a little too real to talk about.

But then I’ve been sitting on it, and pondering it, and turning it around in my mind a little more.

And I started to wonder: Is it possible that someone else out there has struggled to make meaningful connections in a new place? Is it possible that other people find it hard to make friends? Is it possible that you feel lonely, sometimes, too?

Maybe, yes.

So. Here’s the deal: Sometimes, I feel lonely. I’m afraid to talk about this too much because I don’t want people to think I’m just desperate, but truthfully? Sometimes, I feel desperately alone.

I go to Whole Foods and peruse the deli counter just because I know the deli man is extra gregarious and will probably swap a few sassy lines with me, giving me the most social interaction I’ve had all day.

I go to networking events and try to stand up straight and smile big and explain that yes, I’m an e-learning developer but really I’m a sailor and I’m not looking to sell them anything I just want a friend which seems to be much harder to find than a new opportunity!

I go to Starbucks and smile at the girls in line, trying to send a “let’s be friends!” message without crossing the line into creepy (which is actually really hard to do).

I run the popular (and beautiful!) Eastern Prom route, smiling and offering a cheery “good morning!” to anyone who makes eye contact and secretly wondering if I could trip them and start a life-long friendship over skinned knees.

I listen to podcasts non-stop, just to have SOME form of company during the day.

I LOOK FORWARD to weekly work phone meetings. ‘Nuf said.

Heck, I’ve even started buying and selling stuff on Craigslist as a way to just GET IN FRONT of people, on the phone, via email, in sketchy parking lots, etc. (Aside: if you need a new dinghy, I’m your girl. Leah Kruger, Boat Broker 😉 )

In short, I’m smiling my face off in as many random locations as I can come up with, and it’s not quite working.

Smiling my face off is not currently working

Dear Internet, my name is Leah Kruger, I’m 27 years old and I have completely forgotten how to make friends. I love my husband, our boat, our new life in the city, my work, my new metalsmithing hobby, my family and my friends who are far away… but I so crave a local connection, someone to call up at 1:30 on a Tuesday afternoon and say “hey, I can’t stare at my computer screen for another minute, let’s have coffee”.

Some of the latest metalsmithing fun...

Some of the latest metalsmithing fun…

My mom suggested I need to let it go. Stop trying so hard. Find things I enjoy doing and let connections happen naturally.

But gosh-darnit, dear internet, that is a hard thing for a control-loving, step-oriented being like me to do.

(So I’m whining to you instead)

I don’t have an answer yet. But I haven’t (quite) given up, and my smiling face hasn’t (quite) fallen off yet, so I’ll keep trying.

In the meantime, friendly Mainers who like Tuesday-afternoon-coffees, please get in touch 🙂




How do you make friends in the modern world? (A question from Portland, Maine) — 33 Comments

  1. First of all, that’s some pretty amazing jewelry, girl. You’re so talented!
    OK, back to the question at hand. When I moved to the east bay and left my SF pals that I could call up for happy hours and last minute fun outings, I joined a community choir, because I love to sing. I met awesome people that I’m still friends with. What do you enjoy that you can join? Yacht Club? Jewelry making group? Maybe a cooking class? What if you taught sailing lessons locally? You know your stuff, so it couldn’t hurt to look into it. How about a small business group? You could meet others like you who are self-employed (my brother in law joined a group like this. Not only met cool people but made great connections for work). How about team in training? It’s a great cause and full of young, energetic adults. Anyway, just some suggestions, but it’s really up to you what interests you.
    You’re mom is right too. Don’t try too hard, just be yourself and give it some time. Hugs!

    • Thanks Stephanie — it’s remarkable how much just hearing someone say, “I’ve been there, I get it” can make you feel better!! And those are some super good ideas too… I’m looking into them all right now!!!

  2. Been living here for many years. First thing we noticed when we moved here is no one looks you in the eye (New England trait). Don’t get me wrong – we’ve met a lot of great folks here who will go out of their way to help you. Life long Mainers are an interesting lot, but in generalities, I find it hard to easily penetrate that shell of Eastern reserve. It’s almost as if, what with family, current friends, and other commitments, there is little time to make new friends. Having said that, we have some great friends, but it took a lot of effort and quite a while. It could be construed that the fierce, independent spirit staves off those approaches. Now, your hubby may disagree with this …..
    Head over to the Portland Yacht Club in Falmouth and ask about crewing on some of the regular weekday evening races, before the sun fades away.
    Hang in there and I know what you mean.

    • YES, that’s exactly what it feels like… generally I find people to be very open to an initial get together, but hard to actually BOND with. This is probably true in many places, but being “from away” in Maine seems to have it’s own brand of quirks. If you figure out the secrets can you share? 😉 And in the meantime I’ll continue taking all suggestions & trying all sorts of new friend-making activities 🙂

      • Hey Leah –
        Not sure if you and Jonathon would be interested …. one of our boat neighbors in the Falmouth anchorage is having their annual Summer Whooha party at their house Friday night, 8/14. A magician and a folk artist are performing. BBQ theme, bring a side dish, BYOB. Send me an email if you are interested. The neighbors intend to live aboard next year, me this fall. Never been to one before so I can’t tell you age bracket.

  3. I agree with the previous commenter, join a group of some sort. Join a bunch of groups, what the heck.

    What a wonderful, vulnerable, honest subject you brought up! Thank you for having the guts to do it. As scary as it is, the window into a real persons personal life makes a story special.

    I’m not in Portland, but I love that town. My cousin’s parents live in Freeport, are (excellent, lifelong) sailors, and might be fun old-timers to hang out with occasionally. I’ll point them to your blog.

    I’ve been told to spend no more than 10% of my time on a problem, and at least 90% of my time on solutions. If you try something and it isn’t a solution, try another one. I’m feeling pretty low on my boat in Florida right now too, and just last night realized I was thinking way too much about the problem and not nearly enough about the solution. Today is a different story.

    Keep smiling.

    • That is great advice Nate. I like the 90/10 rule especially. And at least joining a bunch of groups means I may end up with a bunch of great new hobbies, right?? 😀

      Also, I can’t agree more about the windows into real people’s real lives… I think that’s what makes blogs, cruising, and stories so powerful. “You too? Me too!” is an incredibly empowering experience.

      Lastly: The end of cruising is an interesting thing. Not that we’re calling this “the end” (for we most definitely and adamantly are avoiding even *considering* this to be the end!), but achieving a goal, working hard for something and then accomplishing it (or not) and moving on… it’s like a small death and a small victory all in one. Would love to read more about how you guys find “adjusting to real life” in Colorado 🙂

  4. Hi Leah! I’d love to be your Tuesday afternoon coffee buddy, if I only I lived on the east coast instead of the west! Hang in there! Have you considered looking into It’s a site that organizes casual get-togethers among people with shared interests. Will you two be heading out cruising again at any point in the foreseeable future? ~Jessie

    • Gah if only America were a little skinnier, we could zip back and forth for Tuesday coffees all the time, right??
      Thanks for the comment, it honestly makes me feel *connected* in that little tiny way that is so hard to find! And I just joined meetup so hoping to find some interesting communities (or at least good stories!) out of that!!

      We are absolutely going cruising again — but we need this time here to restock the cruising kitty, finish my dual-citizenship, and give Brio some much needed love & TLC. Poor girl has taken such good care of us, it’s time to give back a little 🙂 And if I’m completely honest, it’s an EXCELLENT reminder of why we love cruising so much and just how lucky we’ve been to experience that life so far… it gets way too easy to start taking sunsets and dolphins for granted, so a good dose of real world reality is feeling rather healthy 😉

  5. Leah,

    You and your husband both sound great!

    My wife and I live in Freeport and are certainly lifelong sailors. Trouble is we’re OLD (60’s). I’m responding because I was clued in by friend, relative & sailor Nathan Moore (Moore Better World blog) now in Florida. Anyway, I have a daughter much nearer your age. She and her husband live just North of Boston but may move this way within a year. They are great sailors too. Unfortunately I don’t have great connections in Portland but will pass your blog to Elissa (my daughter). She may want to connect when in Portland (not too infrequent).

    All the best, D

    • Thanks so much for the comment Dana — and I love the age disclaimer!!! I seem to be much better at making friends about 3 decades older than me, so I never consider age a barrier 🙂 Especially if you’re salty sailors!! Would love to connect (with you guys or your daughter) so please email or reach out any time!

  6. Hi Leah!
    My cousins, who’ve been cruising and living aboard a 36′ junk-rig schooner, have been following your blog and pinged me after reading your last post. I currently live in the Boston area, but grew up in Maine, and spent time in the Portland area (can’t wait to get back).

    If you’re interested in getting involved in any fun clubs or activities that would offer a social outlet, PortSports Social Club ( offers a lot of fun and low-key social sports leagues. I played volleyball for a couple seasons with them, and am not a talented volleyball player, but had a lot of fun!

    Sail Maine ( is another great avenue that I was involved with when I was in the area. They offer summer sailing programs and host a bunch of local high school sailing teams in the spring and fall. They are always looking for part-time high school sailing coaches to help run practices, and are a fun crowd.

    Feel free to reach out with any questions. I love Maine and the Portland area, and am always happy to spout about it!

    • I’m feeling very cared for by you and your whole network!!! Funny how a few blog comments can make you feel completely connected!
      I’d heard about Port Sports but couldn’t remember the name… I will definitely check that out!! And I actually *just* met the director of Sail Maine so I’m hoping to become involved with them… such a cool organization dedicated to a subject so near and dear to my heart!!! Let me know if you’re ever in the area and I’d love to grab coffee and pick your brain on Portland’s highlights a little more 🙂

  7. Tricky tricky, you’ve really won me over with your blog now.

    The honest truth is that if you intend to cruise then this won’t go away. I feel like two people sometimes. I always want to move on and travel but every big place I hope to make quick connections.

    • Even worse some of my long standing friends are as strong as ever but others are lost. This life is more than worth it but it has it’s down sides. I wish you all the best but you need to find peace within (or without?!)

      • (and this is also an interesting thought… is this maybe the opportunity to learn how to be happy as an individual? to lessen the holds of extrovertism and embrace my inner (very hidden) introvert??)

    • Haha oh I think you’ve hit the nail on the head! Learning to make friends (fast!) is definitely a skill that needs to be practiced, nurtured and not forgotten. Especially since when you look back at life I honestly believe it’s *the people* and the interactions you had with those people that will stick long after the memories of places/objects/experiences have faded.

  8. Hi Leah,

    I don’t have any answers for you, but I will agree with you that it can be difficult to make friends in any way that makes sense. I’ve met people online that are now lifelong friends (in the real world) yet I don’t really know some of my neighbors that I have lived next door to for 15 years. What is the logic in that?

    In any case, my wife and I live on a lake about 1.5 hrs from you in New Hampshire and if you two ever want a change of scenery we would be more than happy to entertain. We are about a year out from our own sailing adventure (we have a Tartan 37 in RI) and would love to pick your brains. I know this isn’t the “Tuesday afternoon coffee buddy” opportunity you might like, but it is what it is. Who knows?

    Best regards,

    Rich and Ruthie
    sv Spirit

    • Yes, yes, yes, exactly! How is it that I can read this comment from you and think, “yep, time to hop in the car and go for a visit to RI” but can’t quite ask the yogi on the mat beside me if she wants to grab coffee after class? We humans are complicated beings 😉

      I LOVE hearing about other people’s plans and upcoming adventures, and would welcome the chance to get together and chat. Are you weekenders / workers / retired / around? 🙂

  9. Leah, I can’t imagine that you, wonderful, strong,smart and fun Leah is having problems finding friends! Stephanie mentioned a lot of good ideas. Another one is maybe you could start a catchphrase club :-). Hugs to you!

    • I love it Bonnie!! Catchphrase club is not one I’d come up with yet 😉 And lord knows we’ve made some friends over that ticking time clock!! “Or we could ship Brio to Bellingham and be neighbours with Kist” is an option that gets thrown around more often than you might imagine 🙂

      • Relocating to Bellingham, what a good idea! We just got back from vacation in the Gulf and San Juan Islands and once again am reminded of what a beautiful part of the world we live in.

        Please let us know if you make it back our way…we’re only a catchphrase game away ;-).

  10. Leah – hard to believe you could have a hard time meeting folks but then again not so hard. I always thought that the challenges were location specific but it sounds like that’s not the case. I guess the only hope is to continue exposing yourself (not literally) in those situations where shared interests might draw you together. I consider you a friend and mentor given your life experiences, but am a bit far off for random coffee get togethers. Hope it gets better!

    • Darryl I feel like I can stay connected with the whole Lapaire family through your blog and facebook updates — it’s the wonder (and weirdness) of the internet world, right? But honestly I am LOVING your stories and honesty, and hope you’ll continue to share the good, the bad and the amazing!!

  11. OMG Leah it’s like you are talking about me! It’s been the hardest place ever to make friends here and I have lived many places! Like you I have my own online business and I also get very lonely. It gets easier after 4 years but I have to say it’s still a challenge. People are not too relational here in general. So my dear you are not alone! Often I am too tired to go to Portland but I would be happy to meet you for a cup of tea or coffee maybe halfway…like Falmouth! Just an idea. You have such a happy, fun and lively personality and need to use that to connect with people. Have you thought about working at the Paint Bar on Commercial st? My 2 daughters are taking me there for my Birthday on Sunday, I have never been there and I am looking forward to it even though I haven’t painted in many years. I hope you still have my phone #. Otherwise send me an email. Would love to get together.

    • Yep, I think the online business part is definitely not helping — even though I know we both love our work!! It’s an interesting challenge!! I’m looking at some “co-working spaces” in Portland (where maybe there will be other lonely online workers that want to have coffee in the afternoons :D) so I’ll let you know how that goes. In the meantime, I would love to have coffee with you again soon!! I just sent you an email 🙂

  12. I am only three weeks into this new life of ours and I am wondering about how I will get some much needed social interactions for myself outside of Darryl and the girls. I struggle with getting my foot in the door when it comes to meeting new people, so I am the last person to provide you with any kind of advice. I hope you are able to get your Tuesday afternoon coffee soon, as I know how important it is to have people close by to connect with. Look forward to hearing how it works out for you as I have no doubt it will happen since I know how much I loved the brief time you and I connected.

    • Oh yes, THAT is its own challenge!! I remember having a bread-making afternoon with another female sailor and literally just saying “IT’S SO NICE TO BE AROUND ANOTHER WOMAN” for about ten minutes. The wonder (and challenge) is you get SO MUCH TIME together as a family… but not always much time (at all) alone! The grass is always greener and all… 🙂

  13. Hmm< I a little late in throwing my two cents in. All the suggestions are great. I know in the Okanagan it is hard. What about a hiking group? Or is there a rec centre you can get involved in. Teach a course, not necessarily sailing but something else you are passionate at. Teach a night school class. People thinking of sailing offshore, pros and cons. Connect with a photo studio and do a travel show on your trip. We have been to a couple and they always get travel type people. Do an explore Maine trip, advertise and take some people, share costs. Anyway, my two "sense" worth! UJ

    • Oh no, I hadn’t even realized that there were comments on this post, so I’m right there with you!! I like this idea of teaching classes… if you can’t find a group of friends to join, make one? An excellent idea to explore! Especially since I think there MUST be other “remote workers” in the area that want to shake off computer brain for a while too!!!! Love & hugs to you and Auntie Lois 🙂

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  15. I am coming up on 7 years here in Maine with no real connections beyond my husband and kids. I came from CT. Not another planet. Though you’d think so. My husband (he’s a Mainer) and I have had one bizarre experience after another. Lots of “yeah yeah yeah!” and then getting completely dumped without explanation. We had so many wonderful friends back in CT. Here is a totally different story. What gives?

    • Feel weird commenting on a post from 2015, but if you are like me, and reading these in 2021, after a year and several months of being socially isolated due to Covid, I thought it might be worthwhile leaving a comment. Yes, we Mainers are hard to get to know, especially when we’re in our native environment. Many of us have lived here our whole lives, and have built friendships and trust over decades. Our extended families live here. We seldom have to get out of our comfort zone. Poke at us – it may take multiple tries to have even us extroverts be willing to connect with folks “from away”, but we will both be richer as a result!

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