Dating in your 40s

By Globe Staff  

Q. Where is a single woman in her 40s supposed to look for love? Though I had some decent luck in my 20s, it doesn’t seem that online dating is a viable option when you are midlife and not interested in hookups, and I tend to see the same people on all the different sites. Once upon a time it was fresh and attracted a lot of different people, but it seems that online dating has run its course as a legitimate way to meet people, based on my experiences.

I’ve tried joining Meetup groups, but as a straight female I’ve been disappointed to find that no matter the topic, it’s mostly women who show up. And meeting people through friends is no longer an option, as everyone is settled and focused on their families. I’ve been feeling so lonely lately and longing for a venue to meet others — but where? Do you or your readers have any advice? There must be others my age who are just as frustrated, but how do I find them? I’m truly at a loss.


Still Searching

(P.S. Would Love Letters consider hosting an event for singles over 40? Pretty please?)

A. The first thing to know is that I get this kind of letter from people in their 20s and 30s. Those younger people do tend to have more romantic options (and more time to explore them), but they face other problems. Some complain that everyone their age is transient. Some say their peers are always attached to their cellphones, looking for better options.

My advice is to continue the online dating — because you never know. You should also try to pursue some activities that put you in groups of people of all ages. I know you want to meet someone who’s 40-ish, but it might be a 33-year-old friend who knows your match. Maybe that 33-year-old friend will turn out to be your match.

In my own life, I’ve learned that having close friends of different ages helps me feel like less of an outlier among my peers, and reminds me that I can wind up sharing plenty with someone, even if they’re in a different phase of life. Having older and younger friends makes the world seem bigger — and a lot less lonely.


Stop looking for peers and focus on looking for people. The bigger your world, the more options you’ll have. That’s why Love Letters events are open to everyone.



There are real people online over age 40. (and 50, and 60, etc. . .) And they’re at museums, and bookstores, and protests, and hikes, and concerts, and lectures. . . . I’ve been where you are, and they’re out there. Good ones, too. WIZEN

Stop listing all the negatives and reasons it won’t work, I suspect some of that attitude is leaking out when you do go on dates.


Online dating is absolutely abysmal. I gave up because I was finding it hard to even feign excitement at meeting anyone anymore and realized my attitude was off-putting and I was probably shooting myself in the foot. Maybe I sound pathetic, but I’ve just started going out and doing things I like to do by myself. At some point maybe I’ll run into someone decent, but if not, I had fun anyway.



I met the love of my life online last year and I am 52. Granted, it took 8 years of searching, on and off. Online dating should not be your sole or even primary focus, but to rule it out is to cut off one of the primary ways people in their 40s and 50s meet. There is no magic bullet. Live your life, keep all options open, make yourself happy in the meantime.


SWM, in his 40s. In my experience, you’ve just got to keep contacting people, and hope for a connection. Try different/multiple sites. Not much better from a male’s point of view — i.e., some women are reluctant to give their phone number. I give mine and times to call — and they don’t call. And they initiated contact with me! (sigh) GDCATCH

GDCATCH, Cold drinks, 8PM? :-)


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