Dear Anna,

I’ve never been on a real date, and I’ve never been in a relationship. Whenever I’m asked on a “date,” it turns into a hookup really fast — or sometimes it was basically a booty call from the start. And like a dumb a**, I let it happen.

I’m tired of accepting that I’ll never be in a relationship and that I’ll ...Read more

Another day, another set of dating questions. In my now 15 years of being a dating coach, the questions have changed over time. In 2011, when sites like Match.com, eHarmony and OkCupid reigned supreme, things were slower paced. (Not quite, “It’s lost in the mail,” but you get it.)

Now, with dating apps at our fingertips and texting being ...Read more

Whether it’s at work, in our personal lives or even something as specific as cooking dinner every night, we all experience burnout at one time or another. So, it’s no surprise that online dating is no exception to the rule.

Finding a romantic relationship may feel like the top priority at times, but that is going to be a lot harder if you�...Read more

Dear Anna,

I could use your help. I rent a parking space during the workweek from a very charming woman who lives in the building across from my office. A coworker connected us through the doorman when I was looking for a space.

From the first time we spoke, there was a … familiarity. She asked if we’d met before. She’s always been kind ...Read more

Dear Anna,

My boyfriend and I have been together for a little over two years. We live together with his two boys and my son. About a year ago, I found out he had been cheating on me. He was messaging women on dating apps and Craigslist, and he was also talking to and possibly hooking up with trans women. I found emails and texts with several ...Read more

Another day, another set of dating questions. Have any of these been on your mind lately?

Q: Is it OK to ask for/take a break from the relationship I’m in if I am feeling stressed out by it?

A: If your relationship is making you feel stressed out, taking a break will not get to the bottom of it.

This is really where you have to do some ...Read more

We have another batch of dating and relationship questions today. Get ready!

Q: How do I heal after a sudden breakup? I feel no desire to ever date again.

A: What you're feeling right now is completely normal. It feels like your heart is literally broken. You feel like you never want to date again. Don't try to override that feeling. It's part...Read more

Dear Anna,

My girlfriend and I have been together for a while, and we have a genuinely loving, solid relationship. The one real struggle is our sex life. This isn’t a case of the mythical “lesbian dead bed,” because we’ve never had a lot of sex. From the beginning, she’s had reasons for not being in the mood — weight gain, stress, ...Read more

Dear Anna,

I’m 32 and my boyfriend of three years constantly prioritizes other women over me in small but consistent ways, and it’s driving me crazy. He’s a generally nice guy — the kind who prides himself on being helpful and chivalrous — but somehow I’m never the one receiving that treatment. A few recent examples: We were at the ...Read more

We’ve all heard the sayings “less is more” and “quality over quantity,” and in many ways, those phrases apply to the world of online dating, at least in terms of how many dating apps you should use. But with all the platforms available, it’s common for single people to be using more than one app at the same time… in fact, I ...Read more