Writing a dating profile can feel daunting. There’s no disputing that, even if you only have to write 750 characters about yourself (that’s about average for most of the dating apps these days … very short, I know). It’s still hard to figure out which exact 750 characters to share.

Too often, a client comes to me asking, “How do I ...Read more

Writing a dating profile can feel daunting. There’s no disputing that, even if you only have to write 750 characters about yourself (that’s about average for most of the dating apps these days … very short, I know). It’s still hard to figure out which exact 750 characters to share.

Too often, a client comes to me asking, “How do I ...Read more

Dear Anna,

I’m a 28-year-old woman who moved in with my boyfriend (30) after only four months of dating. It wasn't planned — my lease was ending, his roommate moved out and it just made sense financially and logistically. Plus, we were spending every night together anyway, so why pay for two places? We've now been living together for two ...Read more

Q: We’re two months in. Everything else is great, but he says we have no chemistry. Can it build? Give it more time?

A: I have a genuine question for you: Why would you want to be with someone who tells you that he has "no chemistry" (those are strong words) with you? Don't you think you deserve that, at a minimum?

With men, no, chemistry ...Read more

As Neil Sedaka so beautifully and succinctly put it (in both boppy and ballad form… I personally prefer the latter!), breaking up is hard to do. Today, we have four questions, all revolving around breakups. They’re never easy, but with time, patience, and perspective, they can be manageable.

Q: How long does it take to get over a breakup?

...Read more

As Neil Sedaka so beautifully and succinctly put it (in both boppy and ballad form… I personally prefer the latter!), breaking up is hard to do. Today, we have four questions, all revolving around breakups. They’re never easy, but with time, patience, and perspective, they can be manageable.

Q: How long does it take to get over a breakup?

...Read more

Dear Anna,

I’ve been with my girlfriend for about a year. Things have been great overall. But lately she’s become fixated on one of her close friends, not in a romantic way — more in a spiral of comparison. Her friend is pretty, but so is my girlfriend, except when she makes self-deprecating comments about how she “could never compete�...Read more

Dear Anna,

I’ve been with my boyfriend for almost two years. He’s a total tech guy — the kind who buys every new gadget, talks to his smart home like it’s a pet, and stays way too late tinkering with AI tools “just to see what they can do.” I’ve always thought it was kind of endearing, if occasionally exhausting.

But last month, ...Read more

Dear Anna,

I’ve been with my boyfriend for almost two years. He’s a total tech guy — the kind who buys every new gadget, talks to his smart home like it’s a pet, and stays way too late tinkering with AI tools “just to see what they can do.” I’ve always thought it was kind of endearing, if occasionally exhausting.

But last month, ...Read more

We have a range of questions today, from hairpieces (!!) to the ghosting (hint: don’t do it) to someone slowly pulling back after a number of great dates.

Let’s get into it…

Q: On our third date, he admitted that he's bald and wears a hairpiece. Am I wrong to feel cheated?

A: If somebody does something to enhance their looks to make ...Read more

We have a range of questions today, from hairpieces (!!) to the ghosting (hint: don’t do it) to someone slowly pulling back after a number of great dates.

Let’s get into it…

Q: On our third date, he admitted that he's bald and wears a hairpiece. Am I wrong to feel cheated?

A: If somebody does something to enhance their looks to make ...Read more

Dear Anna,

I’m 27 and have been with my boyfriend (29) for almost three years. We care about each other deeply, but lately I’ve started to notice how different we are in our day-to-day lives. I’m someone who likes structure — I meal prep, budget and plan things out weeks in advance. He’s more of a “let’s see what happens” kind ...Read more