Money & Careers

Finding Friends Fast—Wherever You Are (Version 2.0)

Karen O’Connor

Karen O’Connor lives light. Sixteen years ago, when she retired at 52 from her career at IBM, she sold everything she owned and went off sailing with her second husband. “We wanted to really see the world,” she says, “so we’d sail maybe 30 miles, then stop at the next town; we traced the coasts of Mexico, Central America, the Eastern Seaboard, the Caribbean, and the Mediterranean.”

After eight years on their 50-foot ketch, they sold the boat in Spain “Then,” Karen says, chuckling, “I got divorced.” And she stayed possession-free: “I rent completely furnished apartments—including dishes and linens.” That’s so she can get in and out of town fast, for ever since her sailing days, Karen has been impelled to move from one city to another every two years. Wherever she settles (briefly), she expects to make friends fast.

Women’s Voices originally published this article on February 27, 2012, when Karen was living in New York City. Since then she’s spent two years as a resident of San Diego, and now she’s using her well-honed friend-gathering methods in Santa Fe. This is an update of her original article.—Ed.

My post-retirement life-change was a rather dramatic transition from a 30-year career at one company to the sailing life. When I chose that life, I knew nothing about sailing, and I still don’t. I was the galley slave and did watches; my husband was an accomplished sailor and could sail the boat himself. I knew enough that if he fell overboard and died, I could get the boat to shore. I knew how to turn the engine on.

When that phase ended, I wanted to continue traveling. Since all I owned was my clothes and a few other personal possessions, I had a lot of flexibility. So I made up my mind to move to anyplace in the United States that interested me and that I had never lived in before. I would be there for at least a year, no more than two. That would force me to be a resident, not a tourist; it would mean I’d need to get involved in the community and make local friends; that I would have ample time to really explore and understand the community, rather than just hitting the tourist highlights.

So I tried it. I rented a completely furnished house in a community near Austin, Texas—and found I liked living there so much that I couldn’t leave in a year, or even two; I stayed nearly three. Then I followed my plan and moved to New York, renting a furnished apartment in Manhattan. I stayed there nearly two years, then moved on to my next destination, San Diego. [See Karen’s note at the end of the article on how her methods have worked in her two latest cities.]

I am certainly not proposing my lifestyle for others. My life—during my career (which required many moves) and since retirement—has given me a lot of experience in making transitions and meeting people in a variety of circumstances. Here are my suggestions for figuring out what you are going to do with yourself, and how to make new friends, after a major life transition . . . whether you’re moving to a new place, retiring, losing your spouse/partner, or whatever else has dramatically impacted you.

What pleases you?
Are you looking to meet other thoughtful, articulate book mavens? Do you own a small business? like rock-climbing? do artful digital photography? play poker? Are you an environmentalist?, a free Internet site, lists shared-interest-group meetings all over the country. You can search for these gatherings by city or Zip Code.

These friends, who met in The Transition Network’s San Francisco chapter, hike in the hills near Berkeley.

Meetup has been an invaluable help in getting me connected in a new city. I’m reluctant to go to the gatherings that are held in a stranger’s home, but many groups meet in public places. I’ve joined hiking groups and explore-the-city groups that met in public spots. Fitness groups meet in parks, book clubs meet in libraries; movie groups meet at the movies and then go to a restaurant afterward for a meal and discussion. When you have a spare moment, why not check Meetup out? The “Drinking Skeptically” or “Witches” Meetup Groups may not be for you (or they may!), but—as I did—you might actually find something you want to do.

The Web has guided me to lively groups full of savvy, like-minded people—potential friends. I suggest using phrases like “professional women’s groups in . . .” or “weekend hiking groups in . . .” That kind of search turned up, for me, The Transition Network. (I can’t remember what search term got me there.) This nonprofit organization was founded expressly to kindle professional women “50 and forward” into continuing their lives of learning, engagement, and leadership in the world—that is, to finding new passions and new friendships in the second half of life.

If you live in a city that has a TTN chapter (12 cities do, with more in formation), I most definitely recommend that you check the organization out—I sincerely believe that TTN has something to offer you, no matter what you may be looking for. I joined the flagship New York City chapter, whose 500-plus members are organized into more than 40 peer groups that hold intimate monthly gatherings.  If there isn’t a chapter in your city, you might want to contact the national organization at the link above to see if there are other women in your city who are interested, and then you can work with these women to start a chapter. [See our detailed article on TTN, “The Transition Network: Helping Women Savor the Second Half of Life.”]

Volunteer work really makes you a part of the community. I happen to be addicted to reading, and libraries have played an important part in my life, so I tend to look for opportunities in libraries everywhere I go.  But I also pursue other opportunities—and there are plenty: museums, schools, hospitals, senior centers, zoos, parks. You can even find short-term volunteer jobs.  For example, I volunteered at the New York City Marathon for two years.  Volunteering not only serves to give you something to do that you enjoy and to help you meet people with similar interests, it also is a nice way of giving to others.

Groups like New York Cares, New York City’s largest volunteer organization, can be an easy portal to volunteer work. Click on the link and find what the new “hot projects” are. There are all sorts of jobs—spontaneous, “I can do that tomorrow” work as well as short- and long-term commitments. You may choose to spend an afternoon next week (say, spending a few hours helping Afghan women study for their naturalization exam, or helping kids play at a shelter); or short-term projects like helping sophomores study for their PSATs; or much longer projects. New York Cares works with 1,300 nonprofits, city organizations, schools, and libraries; 56,000 volunteers a year “give back” with New York Cares. There may be a similar organization where you live: Chicago has one (Chicago Cares), and so does Washington, D.C. (D.C. Cares).

Karen O’Connor enjoying life.

In this, your fresh phase of life, try something new. I had never really ridden horses before I moved to Austin, so when I was there I took horseback riding lessons. Not only did I meet people at the ranch, but now I have another interest that I can pursue wherever I am.  If you’re a New Yorker, think about becoming a Big Apple Greeter. This is a wonderful way to meet other locals and tourists (who, in my experience, often become good friends who live in interesting places to visit!), and it lets you show off your knowledge of Manhattan. The Greeter website actually makes tourists this touching offer: “How can I spend time with a New Yorker?” Can you imagine that?

And two final bits of advice. First, while you’re working to identify activities and people you’d like to spend time with, get out there and do things you enjoy, even if you have to do them by yourself. I can’t tell you how many movies I have gone to alone, how many hikes and walks I have done alone, exploring an area new to me, how many restaurants I have tried for lunch alone (although I do seem to have a problem trying restaurants alone for dinner), how many museums I have explored alone. In fact, I discovered that I really like exploring museums on my own; now I always make visits solo, in addition to trips with friends. These are completely different experiences, so I make time in my life for both.

The second tip: See beneath the shell. In my first temporary hometown, Austin, people are extremely outgoing and know no strangers. If you stand in a line to checkout in the supermarket, you will be best friends with everyone in the line within 10 minutes. People in Manhattan are quite a bit more reserved . . . in fact, they rarely even make eye contact. I found this alarming at first.  However, I discovered that although they generally won’t make the first move, New Yorkers are extremely friendly once you have approached them. I ended up talking at length with people on the bus just by saying “Good morning” to them, or admiring their outfit, or commenting on the weather. In most cases, they were astounded, but they’d talk to you till they got off the bus.

Making friends in my newest cities: San Diego was quite a change from Manhattan . . . but that’s what I look for! In New York I had four (mostly glorious) seasons; in San Diego I found eternal spring.  In New York I had the daily excitement of the bustling city streets; in San Diego I found most of the people out walking, hiking, and biking along the beaches.  Of course, San Diego is quite a bit slower than New York, but not quite as slow as Santa Fe is proving to be (where “mañana” is considered to be too fast).

And the people? People are friendly everywhere. (Note, though, that I’ve lived mostly in towns, rather than in the country or in suburbia, where the social scene may well be different.) In San Diego I made friends whom I was sad to leave behind. Since this past May I’ve been in Santa Fe, and again my advice is working. I have joined a number of groups and have started volunteering at the local library and at the Botanical Garden. And, luckily for me, there is a TTN chapter here (there wasn’t one in San Diego), which I have joined. 

The great news: In my many homes around the country I’ve met people who have proved to be lasting friends.  I’ve already entertained several of them in my new home in Santa Fe—and, since my new city has some winter months, I fully expect to be visiting my San Diego friends when the weather here gets too cold for me.


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  • Kate & Kim September 28, 2014 at 8:14 pm

    Hi Karen,

    This is such a great piece and so valid. I have had very similar experiences and feel so passionate about helping women solve this common problem I’ve created Kate & Kim here in Sydney, dedicated to helping women find, meet and make new friends.

    Hopefully we’ll be in every major city in the next few years to offer an alternative to meetup – which is an amazing resource but also quite daunting for someone like myself who finds groups a little bit scary!

    I’ll definitely be sending my blog readers to this piece to give them some tips and tricks to find new friends, fast 🙂


  • Roz Warren September 28, 2014 at 3:03 pm

    Enjoyed this piece the first time you ran it. Thanks for the update.