Dear Anna,

I've been dating my boyfriend (36M) for five months, and recently, I found out that he had quite a reputation for sending unsolicited, borderline harassy messages to women online. A coworker of mine showed me some of his old DMs on Instagram — telling her how hot she was, and asking her out repeatedly, even though she never replied...Read more

“In your opinion, why am I still single? I want love to find me!!”

This is a text message I received recently from a frustrated client of mine.

I actually get this question more often than one might think. I replied, “This sounds like a question that can’t be answered over text. But I’ll start here: You’ve had relationships before,...Read more

LOS ANGELES -- As a woman prepares to pitch her friend to an audience of roughly 200 eager singles, a few of their pals skip around the room, hold up cardboard signs that say "Team Jason" and hype up the crowd. A live band plays early 2000s pop music while the eligible bachelor makes his way to the stage and sits on a velvet blue couch under a ...Read more

Dear Anna,

I’m a 40-year-old newly divorced career gal, and dipping my toes back into the dating pool after a long marriage. I’m not looking for anything super serious just yet, but I also don’t want to waste time on people who aren’t genuinely interested or who have wildly different values or goals than I do. The idea of endless dates ...Read more

As anyone who's swiped on Tinder, Hinge or Bumble can attest, some of the photos our eyes come across, well, leave a lot to be desired. In fact, the photos you choose can make or break your profile before someone even reads your bio (which will obviously be well-crafted if you’ve been taking my advice!).

In my 13+ years of helping people with...Read more

PHILADELPHIA — On a Wednesday night around 7, Morgan Steffy arrived at El Rey in Philadelphia's Center City area, following directions from an app she had downloaded two months ago. The app directed the 30-year-old West Philly software engineer to sit at Table 2, where she joined a Temple University doctor, a nomad who works in health care ...Read more

Dear Anna,

I'm a 41-year-old woman, just getting back into dating after an eight-year relationship, which ended a little over a year ago. In the past, I’ve spent so much energy looking out for red flags that I realize I’ve never really paid attention to the good signs — the green flags. As I’m starting to date again, I want to approach ...Read more

A few years ago, I received this emotional question from a former client. I appreciated how she allowed herself to express her feelings in such a raw manner and thought it might be applicable to other readers.

“I’m really struggling with my love life lately. Over the weekend, my family got together for my mom’s birthday, and both of my ...Read more

I learned about the trad wife trend last year when a friend, on the cusp between Gen X and millennial, told me about these beautiful women who make videos of themselves cleaning the house, cooking elaborate meals or playing with their kids. All of these tasks are accomplished while the women are dressed in stylish clothing and wearing a full ...Read more

Dear Anna,

One of my closest friends has been pulling away from our friendship over the last few years. It’s nothing overt or dramatic, but there’s a subtle withdrawal happening. She barely texts me anymore, and it used to be daily. She’s stopped initiating plans, and in the rare instances when we do hang out, she seems kind of distracted...Read more

I did something a few years ago that I don’t usually do — I tried to prove myself wrong. What? I know! Let me explain…

As a dating coach who works with people in both the online dating space and dating in general, the advice I give is what I know to work based on both my 13 years in the business (and, since I’m a former economist, I ...Read more

When Joseph Feminella matched with his would-be wife on Hinge in 2020, he was already growing tired of traditional dating apps. He told her he'd like to meet in person right away, and they met that night.

The pair were married three years later, and Feminella launched his dating app First Round's on Me nationwide in August after a four-year ...Read more

Dear Anna,

I'm a 27-year-old woman, and my boyfriend (31) has always been passionate about political activism. I admire his dedication to causes like climate change and social justice, but lately it feels like our relationship is getting lost in the shuffle. Every conversation turns into a discussion about his latest march or organizing efforts...Read more

In today’s world of dating, it’s easy to get swept up in the excitement of a new connection, especially if you don’t feel one very often. But it’s important to remember that building a genuine relationship takes time and patience. Often, people put too much weight on a potential future before even establishing a present connection.

Just...Read more

LOS ANGELES — When I moved to Los Angeles from New York 20 years ago, I felt like I had landed in an alternate reality — a place where flowers bloomed year-round and a light drizzle was considered a valid reason to cancel plans.

Celebrities of varying sorts dotted the landscape. I spotted Keanu Reeves at the Griddle in West Hollywood and ...Read more

Dear Anna,

I’m a 34-year-old woman who’s been in a relationship with my boyfriend for almost four years. We’re serious — and lately are talking more and more about marriage. But something from my past has been weighing on me, and I’m struggling with whether or not I should tell him.

About five years ago, in a previous relationship, I...Read more

PHILADELPHIA -- Nicole Kerr competed with 134 other women to get the attention of her now-fiancé Fran Smythe, a Deptford, New Jersey, finance manager looking for a “fun down-to-earth girl” to settle down with.

That’s because Smythe’s sister-in-law posted his photos to Date Him: Philly, a private Facebook group with over 20,000 members ...Read more

Nearly all of my clients—probably 99%—express a desire for physical intimacy (which, for simplicity, we'll define as sex, however you define that) in their future relationships. For some, it has always been a top priority, while for others, it’s something they felt was lacking in a previous relationship, making it a key focus for the ...Read more

Dear Anna,

My girlfriend and I are both in our early 30s and have been together for almost four years. We’re both introverts, and honestly, we’re happiest just hanging out at home, watching movies or playing video games. We hardly ever go out — maybe a dinner here and there or a small gathering with close friends, but we generally avoid ...Read more

About two-thirds of the way through every meeting with a new client, I get to the part about what qualities or traits they might be looking for in a partner—physical, mental, etc. (The first, longer part is dedicated to learning about the client so I can write the best online dating profile possible.) From their answer to this question, it’s...Read more