Back in 2019 (and for some reason it graced my mind today), the actress Emma Watson brought attention to singledom, not simply by saying that she is happily single but by naming herself as “self-partnered.” It not only acknowledges the fact that being single is a choice, which many people seem to forget, but it’s a valid one at that.

Too ...Read more

Dear Anna,

I recently got out of a long-term relationship — seven years, monogamous, talked-about-getting-married serious. I’m 34, and this is the first time I’ve been properly single since my mid-20s. It’s been a mix of freeing and terrifying. The dating scene feels like a completely different planet now — apps, situationships, ...Read more

Dear Anna,

I’ve been with my partner for two years in a rocky but loving relationship. Our main issue is his all-consuming passion for photography. He's on his camera club's volunteer committee, attends meetings every Monday, shoots Wednesday and Thursday evenings plus some Fridays, and spends Saturday and Sunday mornings on photo walks. He ...Read more

A question I occasionally get (though, not too often since I mainly work with people in the very early stages of meeting and new relationships) is this: “When should I ask the person I’m dating about their finances?”

This has been especially relevant lately in light of the movie "Materialists" out right now about a matchmaker is ...Read more

Dear Anna,

I've been with my girlfriend for eight months, and I'm starting to feel like I'm competing with her phone for her attention — but not in the way you'd expect. She's become obsessed with AI chatbots. At first I thought it was just a novelty thing, but now when she's stressed about work, upset with her family, or even excited about ...Read more

As a professional in the dating industry, I received a lot of questions over the last week or so about what I thought about the new movie "Materialists." IMDB describes the movie as, “A young, ambitious New York City matchmaker finds herself torn between the perfect match and her imperfect ex.” But, I was less interested in the plot of the ...Read more

Frustrated with dating apps, singles are are shelling out for high-end matchmaking.

“We had our biggest month of sales in the history of the company last month, and we’ve been around for 15 years,” Adam Cohen-Aslatei, CEO of the matchmaking service Three Day Rule says. “Our business is not shrinking.”

And he’s not alone. Demand ...Read more

Today, let’s look at two different questions from two different clients. As always, if one person asks, I can only assume it is applicable to a larger audience. And, interestingly enough, you’ll see that these questions are applicable to any gender and any age.

Question:

I am convinced that online dating is haunted, based upon my ...Read more

Dear Anna,

I'm a 38-year-old gay man living in a midsize city, and I'm completely exhausted by the dating scene here. It feels like every guy I meet on the apps is only interested in hooking up, and when I suggest actually going on a date or getting to know each other first, they either ghost me or tell me I'm "too serious." I've tried being ...Read more

ATLANTA -- “Love Island USA’s” Pop-Up Villa stopped by Atlanta’s Park Tavern recently, and whether you’re entering your dating era or you’re just a fan of the popular show, the free event offered more than a chance to audition.

We spoke with casting director Jodi Thomas to get her thoughts on dating trends, red flags and what really...Read more

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