A woman recently messaged me with a dilemma. She had planned a trip to the Grand Canyon months ago with a platonic male friend. Since then, she started dating someone new, and after one month of exclusivity with her new boyfriend, she told him about the trip. The boyfriend’s reaction? Not good.

Her question to me: “Do I cancel the trip out ...Read more

Dear Anna,

I'm 34 and just came out to myself (and a few close friends) as gay after years of thinking I was just "bad at dating men" or "too picky." Looking back, all the signs were there, but I genuinely thought my lack of attraction to boyfriends was normal and that romantic love was just something that happened in movies. I've spent the ...Read more

I got a question recently from a woman asking me whether she should be concerned that the man she just went out with (he’s 57; she’s 51) had previously been in a relationship with a 23-year-old. My response, based on no additional information about either of them, was: It’s unclear.

To be honest, it was less the age gap that raised a red ...Read more

The other day, a 60-something female, widowed client of mine received a message on Match.com from an accomplished, seemingly nice man. In her first response back to him, she asked – point blank – “Why have you never been married?” He replied very politely, saying that it was a combination of things, some work-related and some more ...Read more

Happy Pride Month, advice-seekers! We’re getting gay this June by answering LGBTQ+ questions. As always, send your dating/sex/relationship que(e)ries to redeyedating@gmail.com.

Dear Anna,

My girlfriend and I (both 28, together for three years) have a solid group of friends from college and work, but we're the only queer couple in the bunch. ...Read more

As always, dating can sometimes feel like a conglomeration of awkward situations, ones we have no idea how to deal with.

I stand by my advice that I give often: I don’t want you to be scared of talking to the very person you supposedly like so much. If they’re a true partner, it will feel like a safe landing place for your concerns and ...Read more

Dear Anna,

My boyfriend and I have been together for two years and recently moved in together. Everything was going great until we started sharing a bed regularly. He claims that my breathing keeps him awake at night — not snoring, just my normal breathing sounds. At first I thought he was joking, but he's completely serious.

He's started ...Read more