Today, we have five questions across all aspects of dating:

Q: How do I manage the grief associated with not finding what I’m looking for?

A: This is an interesting question that can answer in a few different ways.

First, I completely understand what you're saying. Most people's lives don't go in exactly the way they want. So we do have to ...Read more

The Rachels met each other when they were 5 and 6 years old, and they met Lizzy Seitel — who would come to be known as one of the Rachels despite her name — in middle school.

They all lived in the D.C. area, and one weekend they took part in a retreat with Cheder, a progressive Jewish community in the area. In Seitel’s recollection, they ...Read more

Dear Anna,

I’m a 38-year-old woman and recently reconnected with my ex-boyfriend from college, who’s now 40. We dated for two years when we were 22 and 24, and it was intense and meaningful before life pulled us in different directions.

We’ve been back together for about five months now, and he’s everything I remembered, except for one...Read more

PHILADELPHIA -- Chris Summers was born in South Philly and raised by her grandmother and her mother. She knew she was supposed to get married, but she never felt exactly like the people around her.

The main sticking point was sex: she didn’t want to have it, yet she still longed for romantic companionship.

”I really crave connection and ...Read more

If you’ve ever wondered, when dating someone, “How do I express my needs and then decide if it’s a relationship I still want to be in?” I have a framework I’d like you to consider: The Tree of Needs.

You’ll have to use your imagination for this one and picture a tree. At the top, we have your need, whatever that may be. On the next...Read more

Dear Anna,

My girlfriend and I have been together for four years, and we’re constantly fighting about alone time. We both work full time but on different schedules. When she gets home from work, she immediately disappears into the bedroom for at least an hour — sometimes longer — to “decompress.” She insists this isn’t personal and ...Read more

A new batch of questions, and a new batch of answers!

Q: When is it time to ask about how long someone has been single and whether they have been married before? In person or still in the app before meeting?

A: I have a question for you: What are you hoping to garner from this information? Is there a "right" amount of time for someone to have ...Read more

Dear Anna,

My boyfriend of two years is extremely into optimization and data tracking — he logs every workout, tracks his macros, uses a smartwatch to monitor his sleep, and so on. I’ve always found it a little intense but mostly harmless, and honestly, his discipline is part of what attracted me to him in the first place. He motivates me ...Read more

A question that often comes up is, “How honest should I be when telling someone that I don’t want to see them again?”

My quick and easy answer is that, in the early stages, say four or fewer dates, the perfect level of honesty is that you “didn’t feel the connection you’re looking for” or “don’t see yourselves aligned long-...Read more

Dear Anna,

I just got back from spending Christmas with my boyfriend’s family for the first time, and I’m still reeling from how badly it went. His mom made multiple passive-aggressive comments about my job as a freelance graphic designer, his sister openly questioned why we’re not engaged yet after one-and-a-half years together, and his ...Read more

MINNEAPOLIS -- The dust cloud billows up behind your bumper whether you’re headed toward Katie Elvehjem’s farm or away from it. And on a Friday evening in spring 2024, Elvehjem was dreaming about leaving.

“I felt like driving 95 miles per hour down a road somewhere just to get out some steam,” she said. Her cows were calving, and that ...Read more