You’re a planner. You have your calendar color-coded, dinner reservations booked a month in advance, and you know exactly what you’ll be doing on your next vacation, down to which café you’ll stop at for your all-important afternoon iced coffee.

You meet someone who’s all about “going with the flow,” a non-planner who would sooner ...Read more

Dear Anna,

I've been with my boyfriend for two years now. We’re both in our mid-20s. His family is honestly the most toxic group of people I’ve ever encountered, and it's taking a huge toll on me. They’ve caused nothing but chaos and drama, moving in and out of our place, causing fights, skipping bills and even trashing our house. My ...Read more

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