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