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Q. Love your podcast, so here it goes. I can’t seem to find the wherewithal to engage the dating world. I’m mid-40s with a 4-year-old. The last relationship I had ended a year ago and I’ve been wallowing in a delusion that companionship is just going to find me.

Partly, this is a Luddite thing; I engage with a computer all day but can’t do the social network thing. Never had a Book of Faces page, for instance. Part of me just wants to hire someone to do that date setup part, a service you’ve highlighted in your podcast, but it feels a little pathetic. More than that, though, why am I so scared?


I was with my first real adult love through my 20s and beyond, and then had a break before the relationship that gave me my child. That one didn’t last either, though we are good buds and she’s an awesome co-parent. Had one subsequent relationship with an awesome person that ended a year ago. Since then, a lot of nothing.

So, how do I get unstuck? — Stuck

A. “Part of me just wants to hire someone to do that date setup part . . . .”

That’s not a bad idea. And if you don’t want to outsource the job to a stranger, you could ask some friends to help you through the process. On the podcast, as you know, we’ve been following a single 44-year-old woman as she dates around Boston. By Episode 5 I had downloaded her dating app on my phone. I helped her swipe and wound up choosing a few men she wouldn’t have noticed herself.


I can’t say I was any better at finding her a partner than she was, but having a friend involved in the process made it a lot more fun. And a lot less lonely. I’ve noticed that the dating industry is responding to the need for friends to help friends. The new app Ship is set up so that a group of people can swipe on behalf of the same person. Perhaps you can assemble a team to help you look.

As you consider next steps, you should remember that you’ve had a pretty great dating record, based on what you’ve told us. You had a longtime love, a child with someone you seem to like a lot, and a relationship with a person you describe as “awesome.” That is a pretty solid list. Maybe you’re scared because that last relationship ended before you wanted it to (just guessing here), and that’s OK. But please know that your year of nothing has been a part of the process. You needed a break. Now you’re ready to push yourself a little. So do. — Meredith


I’m sure this is going to be an unpopular opinion, but I know a lot of people who have reconnected with people on the “Book of Faces” and are now in happy relationships. Might be worth a shot. MMNNEE

I am sorry you have trouble meeting someone. You seem to be trying really hard in this letter with cutesy phrases like “Book of Faces” and mentioning that you are Luddite. This can come off as obnoxious in real life. And in this letter. Regardless, put your fears of technology and looking “pathetic” aside. Ask your friends for fix-ups, sign up for an online dating service, and engage in a real world activity where you will meet someone with similar interests — an adult education course, trivia night at a bar, a group exercise class. Good luck! WARMACHINE

Submit questions your for Meredith here.

Get Season 2 of Meredith Goldstein’s Love Letters podcast now at loveletters.show or wherever you listen.Column and comments are edited and reprinted from boston.com/loveletters. Send letters to meredith.goldstein@globe.com.