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

Dear Anna,

This feels like a ridiculous question, but here goes. I’m a 22-year-old trans woman, early in my transition, who’s only out to a small circle of close friends. Most of my friends are women, and they’ve been incredibly supportive as I’ve started figuring myself out.

Recently, two different friends — separately, not together...Read more

Fights, disagreements, squabbles — whatever you want to call them, they are part of any relationship (romantic or otherwise). And, I’d venture to say, they are part of any healthy relationship. Disagreements can’t (and shouldn’t) be avoided, but is there a way to disagree productively?

Today, we have two questions regarding ...Read more

Dear Anna,

A few years ago, I fell into an intense long-distance relationship with someone I met through a fandom community. We went from friends to lovers, writing smutty fan fic together and talking every day. They already had a long-term partner, and although they had always considered themselves open, I was the first person they had ...Read more

In any relationship, budding or established, there are two competing philosophies: Take people as they come vs. ask for what you want/need, especially when it comes to certain behaviors. I want to share that these two things can co-exist, and neither has to necessarily take precedence over the other.

Yes, we have to take people as they come, ...Read more