PHILADELPHIA -- Scott Harmon and Mark Williams met each other in a maximum-security prison in the heart of Pennsylvania coal country in 2012.

They had both grown up in the Philly area; both were in their early 20s, at the very beginning of life sentences without the possibility of parole for homicide convictions. Both had sons.

They were also ...Read more

As the world we live in moves further and further online, there is still the opportunity to meet someone in person, or “in the wild,” as it were. I’m talking about meeting IRL — in real life. While there are, of course, no guarantees, if you’re looking to supplement your experience with online dating, I want to make sure we cover the ...Read more

Dear Anna,

I’m 26 and going through my first real breakup. My boyfriend and I have been together for almost four years — he’s my first serious relationship, first love, all of it. We’ve been incredibly happy, but recently some major life circumstances have come up that are pushing us in different directions. There’s technically a way ...Read more

ST. PAUL, Minn. -- The server at Estelle in St. Paul had just brought over some complimentary cheese curds when Amanda Burke skipped the small talk and started to interrogate her new suitor. It was their very first date, and Burke launched into her “dealbreaker” questions:

No. 1: Have you ever cheated on someone?

No. 2: How many times have...Read more

PHILADELPHIA -- McGillin’s Olde Ale House, the 166-year-old pub in Center City long owned by the same family, has determined that being a matchmaker is a strategic advantage in a crowded industry.

Of course they serve draft beer, Philly cheesesteaks, and wings — but the bar has leaned especially hard into being, in its own description, the ...Read more

Dear Anna,

I’ve (36-year-old female) been seeing a new guy (34) for about six weeks — we’ve been on six dates, things are going really well and there’s clearly mutual interest, but we haven’t had the “what are we” conversation yet. Now Valentine’s Day is coming up and I’m completely lost. Do I acknowledge it? Plan something? ...Read more

Dear Anna,

I’ve been seeing someone for about two months. From day one, I told him I’m not on birth control and that condoms are nonnegotiable. Yet every time things get physical, he starts pushing back — asking if we can “just this once” skip it, saying condoms don’t feel as good, or promising he’ll pull out or be careful. We ...Read more

I get a lot of questions that sound something like, “Can you help me write a profile that attracts the type of person I'm looking for?”

In the most loving way, I say, “No, I can't do that.”

And I don’t answer that way to be dismissive. I answer that way because I genuinely don't know what the person you're looking for … is ...Read more

PHILADELPHIA — Franki Jupiter grew up in St. Louis, the son of a Presbyterian minister and a Bible Study teacher. He was raised to believe he should marry young and remain committed — to both Jesus and his wife — for life.

But Jupiter, 39, didn’t end up doing so.

“I love people, and I’m not great with impulse control,” he ...Read more

Dear Anna,

I’m 35 and my girlfriend is 30. She works at a tech startup and has gotten really close with one of her coworkers — a 28-year-old guy who just moved to the city. They’re part of a work friend group that hangs out outside the office pretty regularly. Last weekend, the whole group went to a concert that I wanted to go to, but I ...Read more

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