As a dating coach, I sometimes have mixed feelings about what I learn in my job: On the one hand, I’m glad people feel comfortable enough with me to ask the questions they may not want to share broadly or ask their friends/family. And, on the other hand, well, sometimes I wish I didn’t know what goes on in the darkest depths of someone’s ...Read more

Dear Anna,

I recently started dating someone who's polyamorous. I've always been monogamous but I find myself intrigued by the possibility of exploring this with her. However, I'm worried about jealousy and whether I'm considering this for the right reasons. How do I know if I'm genuinely open to polyamory or just afraid of losing her? — Mono...Read more

Dear Anna,

I moved to a new city for work last month, leaving behind a "situationship" that never quite became official. Now he’s texting wanting to try long distance, saying the new year made him realize what he wants, which is, evidently, me. I'm torn between giving this another chance and making a completely fresh start in my new home. ...Read more

After 13 years of helping people find love (and sometimes dodging a few bullets along the way), I’ve seen the dating landscape evolve dramatically.

Let’s look at five tips for navigating the dating world this upcoming year.

1. Curate your dating profile like it’s a first impression (because it is)

Your dating profile is your personal ...Read more

Question: “I have been dating someone for three months, and we’re exclusive (not seeing other people). I’m ready to define the relationship (DTR) but don’t want to lose him if he’s not ready. How to have the talk?”

My response:

“For better or for worse (and I hope better, of course!), that's a risk you're going to have to take. I...Read more

I received this text from a client I started working with recently: “I really want to solve this issue of people mentioning their exes! Or maybe that’s just normal if you’re divorced? Is it me? Or does that happen to other clients on every single first date? It’s so uncomfortable!”

And then this week, after a different client went on ...Read more

LOS ANGELES -- When David Brown moved from Chicago to Los Angeles this summer, one of the first things he did was download an app that aims to "fight big-city loneliness."

The 35-year-old sales director had seen an Instagram ad for Timeleft, which matches users with strangers for dinner via a personality algorithm. Since he only knew a handful ...Read more

Dear Anna,

When it comes to gifts, my boyfriend of two years kinda phones it in. For my birthday last month, he gave me a gift card to a coffee shop, which was sweet, but I work from home and don’t even drink that much coffee! Last Christmas, I got a generic piece of jewelry that wasn’t my style at all. I’ve tried to tell myself it’s ...Read more

It’s 11 p.m. on Tuesday, and you’re wrapping up a first date. And it was a pretty good one! It ends with a hug goodbye and tentative plans to get together again for dinner early next week (you know, if you ever hear from him again). As you climb into your Lyft and give a final wave to your date, you’re excited that after a string of "mid" ...Read more

Question: “How do you ask if a guy is ready for a relationship if he is ripe off of a five-year relationship?”

This is a question I received recently, and I get some form of the “How do I know if someone else is ready?” question quite frequently.

My response:

“People are notoriously bad at self-assessing their readiness. The only ...Read more

Dear Anna,

Usually Mariah Carey season is my favorite, but this year I’m struggling. Everywhere I look, people are cozying up, planning cute holiday dates and posting about their jolly AF lives. Meanwhile, I’m single, spending my evenings scrolling through dating apps and wondering if I should just settle for someone mediocre so I’m not ...Read more

Dear Anna,

My partner and I broke up in late April but we had a situationship over the summer. I’m a sophomore in college and I’m excited to get back out there. There’s one problem, I have no clue what I’m doing. I’ve only recently started to learn about sexual guilt and shame because I never focused too much on it while in my ...Read more

“How can I write in my online dating profile to attract the type of person I’m looking for?”

This is a question I get, in some form or another, from clients almost daily. In their mind, they have a target partner. Let’s say this “target” is a man in his 60s, well-educated, with grown children, and lives in Philadelphia. Or maybe ...Read more

Dear Anna,

My fiancee and I have been together for three years, and I thought everything was great. Last night, however, during dinner, she brought up something that completely blindsided me: the idea of us each having a "pass" to sleep with someone else before the wedding. She said it would be healthy for our relationship and help us start our...Read more

“Should sex with one person mean you stop going on dates with other people?”

This is a question someone asked me recently. In my line of work as a dating coach, things come up in all areas of the early dating process—how to use the apps efficiently, what to do/say on a first date, when/what to text, how to build connection and chemistry, ...Read more

PHILADELPHIA — The brides wore running gear — sneakers, comfy shirts, and, for one of them, a black ball cap that said “I Do.”

Kara McElvaine and Shelbie Turner got married Saturday while running the Philadelphia Half Marathon, exchanging vows every mile, smiling through the finish line.

“We decided to celebrate being each other’s ...Read more

ATLANTA -- After a contentious election cycle, many people look forward to the holidays as a time to reset. But some of us dread talking about politics with certain family members. Producer Natalie Mendenhall spoke to Drew Westen, a professor emeritus at Emory University and a licensed psychologist.

Here’s that interview with tips for you on ...Read more

Dear Anna,

I’ve been seeing this girl for about two months, and while things have been fun, I’m struggling with how close she still is to her ex. They were together for seven years and broke up six months ago, but it feels like he’s still very present in her life. He even comes over frequently. She has photos of them all over, and her ...Read more

You can’t “create” chemistry, either online or in person, but you can do a few tangible things to increase your odds a bit. I want to share 7 dating mistakes that you can fix right now:

1. Using unflattering profile pictures.

You say, “Does it really matter?” The answer is yes. Yes, it does. You get one chance to make a first ...Read more

CHICAGO -- Lenore Lindsey did not consider herself a baker when she opened Give Me Some Sugah at age 50 in 2008. Neither did Vamarr Hunter when he took over the South Shore bakery this year at the same age.

The late-in-life knack for baking isn’t the only parallel in their stories, first reported by the Chicago Sun-Times. Hunter never dreamed...Read more