I need help figuring out how to date

On June 8 and 9th, the Comedy Studio – now located in Bow Market in Somerville – is hosting a Love Letters weekend for us. There will be Love Letters-themed shows both nights, and on Sunday, we'll be doing a live taping of the podcast. Get your tickets. Join us there. The venue is very cool, and Bow Market is my new favorite place, in general.

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 set-up 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


"Part of me just wants to hire someone to do that date set-up 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 follow 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. 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 for 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, or at least it seems that way in your letter. 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." I mean, 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

Readers? Is it time for this LW to learn how to use some apps?