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

In online dating, I often see two competing factors:

1. People genuinely want to meet someone great (or at least they think they do).

2. People are lazy and don’t take the time to do online dating well … or at all.

This conversation happened to a client of mine (the woman in this exchange) on Bumble:

Her: Do you still drink iced coffee ...Read more

Dear Anna,

I was 23 when I finally got my own place. There was this attractive guy who lived down the hall from me and we had some flirty exchanges that eventually led to a hookup. Just a one-time thing, and afterward we'd only exchange quick hellos if we ran into each other. A few months later, I met my current boyfriend, who I've been with ...Read more

Dear Anna,

My husband and I welcomed our beautiful daughter six months ago, and while we're absolutely in love with her, I feel like my husband and I are just ships passing in the night. Between diaper changes, feedings and sleep deprivation, our relationship has taken a backseat. Date nights seem like a distant memory, and when we do have a ...Read more

Whether you're navigating first-date logistics or attempting to decide dating app behavior, dating today comes with a thousand tiny decisions that can leave you second-guessing.

I get these kinds of questions all the time, so here’s a roundup of real scenarios — with my unfiltered takes — on how to handle them. Spoiler: None of these ...Read more

Dear Anna,

After 12 years of marriage (17 together), I (38F) am ready to end things with my husband (40M). We've had our ups and downs — early struggles when he was unemployed, ongoing imbalance in household responsibilities and communication issues. While I handle most domestic tasks despite earning more, he contributes minimally and seems ...Read more

This article is for anyone trying to get a date with a woman. As a woman myself, and working with 65% female clients of all ages, I have the insider information on what women want when it comes to dating … and what they don’t.

I’m going to break it down in simple terms. Do any of these things, and your chances of getting a date dwindle. ...Read more

Dear Anna,

A few weeks ago, my wife’s friend’s husband (I know, classic game of telephone) told me that my wife had a brief fling with someone at work. He was scant on details so I don’t know if it was emotional or physical or how far it went. Apparently, she ended it quickly, felt awful and swore it off. She hasn’t said a word to me.

...Read more

Dear Anna,

Hi Anna. I’m 40 years old and single. I met someone over a year ago. Things started off well. She mentioned that she wants to spend time together, but when the time comes around I get a reason as to why she can’t make it and it's a repeat process. I feel like I’m being dragged around. What should I do? — Looking At Some ...Read more

Every May, I fly from New York to Austin, Texas, to compete in the annual O. Henry Pun-Off World Championships. Yes, this is a thing … and it’s serious. I’ve now attended five times and have twice come home with a third-place medal and once with a first-place trophy. Win or lose (though hopefully win — fingers crossed!), I know I’m ...Read more

Technology makes people flakier. It’s a sad truth. People can hide behind a screen without seeing someone else’s reaction to their words… or non-words, as is sometimes the case with ghosting. That’s not to say that all people are unreliable or flaky or rude, of course. In fact, most people are not. But the few who are set a negative tone...Read more

Dear Anna,

I’ve been dating my girlfriend for almost 10 months now. I frequently buy her jewelry and sometimes clothing, but she never wears them when we're together. Sometimes I'll ask for photos of her wearing the pieces to see how they look, and she will send one, but I never see them in person. Is this a me problem? Why doesn't she ever ...Read more