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

How many times have you heard something like this?

“I don’t want to waste your time.”

“You’re too good for me.”

“I’m too old/young for you.”

“I’m too short/tall for you.”

“You’ll get annoyed with me trying to keep up.”

Generally, these lines are in response to an initial message on a dating app. For example, a...Read more

Dear Anna,

I (31F) called off my engagement about a year ago and moved to a new city. A few months later I matched with a guy (26M) on an app — the second person I dated post-breakup. We hit it off immediately, but I wrote him off as relationship material: He’s five years younger, still finishing grad school, and had never had a serious ...Read more

For years, I’ve worked with clients who come to me saying the same thing: “I just can’t find the right person.” When I dig a little deeper, a common theme appears — they’re clinging to a very specific idea of who their “type” is. (It often starts with a physical attribute, but it goes beyond that.) Here’s the kicker: That type ...Read more

SACRAMENTO, Calif. — On a summer Tuesday evening, a group of 18 young women gathered at Alma Wine Bar in downtown Sacramento — most of them complete strangers to one another.

By the end of the evening, fueled by a few glasses of wine and a handful of casual board games, new friendships were forged and potentially long-lasting connections ...Read more

Dear Anna,

I’m 44, divorced, and very happily in my “slut era.” I’m dating casually, having fun, and not looking for either one-night stands or The Love of My Life. I’m somewhere in the middle. I want chemistry, good conversation and sex with people I genuinely enjoy spending time with, even if it’s not headed toward forever.

A few...Read more

There’s nothing like a first impression, and in the online dating world, that means your photo and your bio. Admittedly, the photos are the first thing that most people look at. But for the purposes of this article, let’s focus on the written part of a profile.

Talking about yourself is difficult. It’s a delicate process where you try to ...Read more

Dear Anna,

I’m a 36-year-old guy who’s been single for a few years, and lately I’ve started wondering whether I actually like dating anymore — or whether I’m just doing it because it feels like I should and because that’s the dominant narrative, the thing I’ve been told to do. It’s not that I can’t get dates. I go on enough of...Read more

Ghosting — the abrupt disappearance of someone you were seeing or taking to — is jarring. It often comes out of nowhere, and it forces you to first wonder what happened to the other person before it sinks in that they did this intentionally. In short, ghosting is cowardly, avoiding a short, difficult conversation to spare yourself being ...Read more