Dear Anna,

My boyfriend and I have been together for a little over three years now. We recently argued over a work gala I’m attending this Saturday. I want him there for the whole evening, but he doesn’t see why he should give up a whole night for people he barely knows. He offered to come for the last hour or two, but not the full event.

...Read more

I got this email last week from a new client of mine. She is in her 60s, widowed and this is her first foray into online dating:

“Alan has texted me three times and has not suggested getting together. Of course I have done the same. I’m losing interest in continuing this back and forth. I have the sense that he prefers intellectual banter...Read more

The finale of Netflix’s dynamic and delicious retelling of “My Brilliant Career” delivers the kind of love story modern women have been craving.

The six-part miniseries based on the 1901 protofeminist novel follows a talented, wild young woman, Sybylla, played by Australian actor Philippa Northeast, who is recklessly bold and almost feral...Read more

Dear Anna,

I’m a 50-year-old woman. I’ve been married to a woman for almost 14 years, and we’ve been sexless for about 10 of those years. We recently opened up our marriage and I’ve been thoroughly surprised by wanting to be with men for the first time ever. Long story short, I met a man who’s wonderful and sexy and provides all kinds...Read more

This week we have questions ranging from the courtroom (divorce… nothing that scandalous!) to the bedroom….

Question: A match says he's separated but divorce not final yet (almost). Avoid? Alarm bells ringing.

Answer: I don't like absolutes. Especially if someone has children, certain states/countries require you to be legally separated ...Read more

PHILADELPHIA -- Lynsey Lehr grew up knowing that her beloved Aunt Donna survived a near-deadly hit-and-run as a teenager.

The details of the tragedy were part of the tight-knit family’s history.

Donna Eiser had just finished her freshman year at East Stroudsburg University and aimed to become a physical education teacher. Then one night in ...Read more

Today’s questions are all from women in the early stages of dating:

Question: He’s 40, not 38. And he used his middle name in his profile. Told me on the first date. Important for his job to keep low profile. OK?

Answer: Are you asking me to tell you that it's OK that somebody lied about their age by two years and then gave you the excuse ...Read more

Dear Anna,

I’m (27F) told pretty often that I’m out of most guys’ league, looks-wise. The guy I’m dating (36M) is a great person, but he’s not conventionally attractive, and he can’t stop pointing that out. I want to be clear I’m genuinely into him — I’m attracted to him, tell him constantly, and mean it. But whenever we’re ...Read more

CHICAGO -- Mary Kate Reilly’s after-work routine is familiar and comforting. Her 50-minute commute ends at her childhood home in Tinley Park, Illinois, where her mom is waiting when she walks in; she shares a meal and relaxes with her parents afterward as they watch reality TV.

It’s a living situation the 23-year-old did not exactly ...Read more

Dear Anna,

My girlfriend and I recently celebrated our second anniversary. I tried to make it special. I surprised her by booking a little cabin upstate she’d been eyeing for months, planned the whole weekend and cooked her favorite meal from scratch the first night. It wasn’t cheap, but I wanted to do it.

A few days later, she told me I �...Read more

A major dating philosophy of mine is, “You have to hold yourself to the same standard as the person you’re looking for.”

I was working with a client a few years ago—nice guy in his early 40s—and at one of our meetings, he expressed to me what he was looking for in a woman. He mentioned certain physical features, a desired age range ...Read more

PHILADELPHIA -- Elysia Baskins and Christopher Johnson did not intend to raise a child together.

They instantly got along when they first met on Bumble in 2022; they both loved anime and eating Japanese food. But after their first date, Baskins didn’t feel the romantic chemistry, so they became best friends instead.

In 2025, Baskins got ...Read more

Dear Anna,

My wife and I are in our early 30s, married five years, no kids yet. I’ve started quietly looking up divorce lawyers, and I hate that it’s gotten to that point. The root of it is that I can’t trust what she tells me anymore. It’s been a pattern for years — she’ll agree to something, and I later find out she never actually...Read more

I give a lot of advice on how to use the various dating sites and apps, but it’s important to talk about what they are, why we should use them, and some general pointers for having a positive experience.

Online dating is:

--An additional way to meet people

--A screening tool based on things that are important to you

--A way to meet people ...Read more

Since Season 4 of "Ted Lasso" just came out (so far, so good… and I love that he’s coaching a women’s team!), I decided to re-watch the first three seasons. Good TV is good TV. What can I say?

While overall, the show is a comedy, there are some definite pieces of wisdom hidden in there if you look hard enough. One of these is, “All ...Read more

Dear Anna,

My girlfriend and I have been together for six years. We’re in our mid-30s. Like a lot of people, she’s spent most of her life wanting to get fit and lose weight, and for a long time it didn’t really go anywhere. This year her doctor put her on a GLP-1 medication, and combined with a new daily workout routine, it’s actually ...Read more

Dear Anna,

I'm 23, and I've been with my girlfriend for about a year and a half. It’s my first real relationship and I love her, genuinely. She stuck by me through a rough stretch when I was dealing with some family stuff, and I don't take that for granted. Things aren't bad most of the time. We laugh together, we're comfortable, we care ...Read more

Years ago, I had a client who was on Hinge, and someone she was interested in had a really cute picture of himself with a golden retriever. It was his last picture—the sixth of six. So, when she reached out to him, she said, appropriately, “What a cute pup! What’s his/her name?” Simple, cute, easy.

The guy replied (yay!) and, rather ...Read more

PHILADELPHIA -- Linden Curhart describes his home as a “spider web of connections.”

There’s his husband, Teddy Ullrey-Curhart, whom Curhart met when he was an isolated teenager growing up in a conservative town in Virginia. The two always dreamed of getting married, and in June they celebrated their 13-year commitment in a big pink ...Read more

Dear Anna,

I went on a date with a couple recently. I’ve been a unicorn before, so I’m not completely new to the experience, but I wasn’t sure whether it was something I still wanted — and, honestly, I’m still not sure. The date itself was fine! We had fun, and afterward I wanted to see them again, so told them as much. But now I’m ...Read more