Dear Anna,

I’m an experienced threesome participant, but I’ve been happily monogamous for years. Recently, my wife and I decided to try having a threesome together because she never really got to have the fun, slutty 20s experience she wanted. (For context, this is a two women, one nonbinary person situation.) Because it was her first time,...Read more

All too often, I get questions like these from clients:

--“What did they mean when they said that?”

--“How can I ask, ‘What are we?’”

--“Why didn’t they text me this morning like usual?”

--“Why don’t we have plans lined up for the weekend already?”

From my 15 years as a dating coach, I can give an educated guess as ...Read more

PHILADELPHIA -- Duwenavue Santé Johnson and Joseph Carrillo first met in San Francisco when they lived a block apart.

But that arrangement didn’t last. They have now been married for 17 years, and have lived 3,000 miles apart for the majority of the time.

Johnson lives in Philadelphia's Old City neighborhood, where she works as a senior ...Read more

It’s unlikely that I’ll take up cattle ranching at this point in my life, so the ability to saddle up a horse and separate a steer from the herd isn’t a must-have skill.

But do I still want to learn how to do that at a visionary event called the Top Hand Cowgirl Challenge?

Oh, heck yes.

What’s drawing me, and the hundreds of other ...Read more

Black and white, right and wrong, cut and dried. I know how tempting it is to look for a “rule” or a quick answer in dating. Leave or stay? Unmatch or meet? But most things in life are not answered so simply. This week, we have several dating questions looking for a back-and-white answer … and I’m here to show the shades of gray.

...Read more

Dear Anna,

I’ve been dating my boyfriend for about four months, and things have been going really well — or at least I thought they were. He’s always been really thoughtful over text, sending me these sweet, articulate messages about how he’s feeling or why he appreciates me. I’m not the most eloquent person, so I’ve always been a ...Read more

Dear Anna,

I’m 34 and recently got back into dating after a five-year relationship ended about a year ago. I took time to work on myself, went to therapy, and I’m finally ready to put myself out there again. The problem? I’ve completely lost the ability to tell if someone is actually interested in me. I’ve been on maybe eight or nine ...Read more

I recently had someone reach out to me about a dating dilemma: The man she was “dating exclusively” (her words) told her he was no longer on apps. However, a friend spotted his profile, which was not only “active now,” but updated. When this person approached the man about it, he claimed that the app kept his dating profile active for �...Read more

Dear Anna,

I’m 28 and for the past few years, I’ve been fully committed to the casual hookup lifestyle. I’m bisexual and I’ve had a string of no-strings-attached situationships with people I met on apps — probably a dozen or so in the last two years alone. I was totally fine with it. I wasn’t looking for anything serious, and ...Read more

A male client of mine went on 12 dates with a woman over a few months. (For what it’s worth, if you’re still counting the number of dates at this point, I do have to wonder why.) Regardless, my client is looking for a long-term relationship and he wasn’t sure how this woman felt about that. I encouraged him to tell her what he’s looking ...Read more

Dear Anna,

When my husband and I got engaged in our 20s, we were barely scraping by. He proposed without a ring, and we got married not long after with a small, low-key ceremony — no bands, no big gestures, just the two of us building a life together. At the time, it felt completely right. Fifteen years and a couple of kids later, things look...Read more

Another day, another batch of dating questions — some about losing hope in finding a partner, some about defining the relationship, and some about date planning. Perhaps one will especially resonate with you.

Q: We’ve been dating for three months. I’m ready to define the relationship. I'm afraid he might not be ready yet. Bring it up or ...Read more

MINNEAPOLIS -- Five Saturday weddings featured something old, something new, something borrowed and something red. Make that something “read,” since the weddings happened at Minneapolis Central Library.

The weddings took place in 15-minute intervals in Pohlad Hall, with receptions in a nearby meeting room. Each couple were allotted 25 ...Read more

Dear Anna,

My husband and I opened our marriage about six months ago — something we'd talked about for years and finally decided to try. We did everything "right": read the books, had the long conversations, established our agreements. But six months in, the experiment seems to be working for exactly one of us. He has two new partners he sees...Read more

As a dating coach, I get a lot of questions along the lines of, “Are there questions I can ask early to know if someone’s for me long-term?” Or the more blunt, “How can I tell early if I’m about to waste my time?” (For starters, that attitude isn’t helping.)

I’d like to explain an analogy I use called Chicken Nugget Theory.

...Read more

Dear Anna,

My girlfriend and I (both mid-30s, both queer women) have been together for almost two years, and our relationship is solid — we communicate well, trust each other and have a great sex life. Recently, we’ve been talking about the possibility of having a threesome. Neither of us has done this before, and we’re both genuinely ...Read more

Writing an online dating profile can be daunting, and it’s out of a lot of people’s comfort zones. We’re taught not to brag, but isn’t that what online dating is — a chance to showcase who you are? Yes and no.

Talking about yourself is hard — your hobbies and interests and a little background at a minimum. Plus elements of your ...Read more

Across Los Angeles, you can feel the shift in dating without anyone saying it out loud.

Men talk about how hard it’s become to meet someone, while women talk about how peaceful life feels now on their own. The gap between those experiences is often framed as women asking for too much, but that explanation misses what’s actually changed. ...Read more

Dear Anna,

I’ve been with my boyfriend for about a year and a half, and our relationship has been really solid — he’s kind, thoughtful and we’re genuinely happy together. I lost about 80 pounds a few years ago before we met, and he’s only ever known me at my current weight. Last week, my sister showed him an old photo from my high ...Read more

When I saw my parents recently, I thought it would be fun, both as a dating coach and as their daughter, to ask them about how they met and how their relationship progressed. I always knew some details, but I didn’t know the full story. March 16 marked their 46th wedding anniversary, so I would like to give tribute to them in this article.

...Read more