Dear Anna,

I’ve been happily married for 12 years, and my husband and I have been poly for eight of them. Overall, it’s been a really positive part of our relationship. We’ve had our trials, of course, but we communicate much better than we once did, we both date other people occasionally, and I genuinely experience compersion much of the...Read more

Dear Anna,

I’m 28 and have been with my girlfriend for about a year and a half. Things are really good between us overall, but we keep hitting a wall over one specific issue: I occasionally text with an ex from about four years ago. And I do mean occasionally. We’re talking maybe once or twice a month, maybe less than that. And the gist is:...Read more

We have questions today about someone’s potential readiness to be in a relationship, one-word answers in the dating apps, making a good first impression and how to know when it’s time to get back out there after a breakup.

Question: I met a guy. It’s been six months since his separation after more than 20 years of marriage. Is this a deal...Read more

Dear Anna,

I’ve been messaging someone I met on a dating app for about three weeks, and we finally have our first date this weekend. We’ve had some really fun conversations, and I’m genuinely excited to meet her. The other night she mentioned that she’d been reading a book she loved, but her library hold expired before she could finish ...Read more

About 10 years ago, when I was in the first few years of running my business, I was working out of a co-working space. A great place to get work done … and meet people. I remember very clearly when someone I met at the office asked if I’d like to have dinner. I thought it was a nice gesture, and I know how hard it is to muster up the courage...Read more

Dear Anna,

I’m a bi/pan woman who’s been married to my husband for 11 years. I’ve always known I wasn’t straight but never explored it much. I had one relationship with a woman early on, and that was it. I’m not looking to open my marriage or date other people. I just want to find ways to honor this part of myself that’s always been...Read more

Like it or not, dating apps are the most ubiquitous way to meet new people these days. In my 15 years of being a dating coach, I’ve seen thousands of happy relationships start this way. But I’ve also heard all the shortcomings: “It takes up too much time.” “I’m not getting the matches I’m looking for.” “There’s no one good.�...Read more