In the (barely) over 50 dating category, are women still "expected" to have sex with the guy on/following the 3rd date or the 3rd week for that matter? To ...

When dating, how many dates should the man offer to pay for all the dates. When is it okay to go Dutch? I want to say that things should be split 50/50 from ...

We talk about getting dumped on Zoom aka "zumped", a man with the lamest excuse for breaking up with his girlfriend and why you keep meeting men just looki...

With a light flickering oh-so dimly up ahead signaling the end to our days in isolation, a new question is emerging: Will dating — specifically how we get da...

Kevin asks: I have met 40-year-old women who are tentative about kissing after dinner or drinks at my place on the second or third (!) date.  They worry th...

By all accounts, Emma is a catch. She’s funny, kind, and attractive. She works a job she loves and is described by many as a social butterfly. So why do so...

I'm not a fan of the new Instagram trend of posting trashy dating app messages hoping to become an influencer. Most of those accounts are run by people who a...

There are certain terms people use in their bios that should be avoided.

Anne asks: I’ve been on the Bumble app and the OkCupid all for over seven months and I loathe them. All of my Bumble dates have been nightmares, and OkCupi...

TJ asks: I have a really quick question with almost no drama...if such a thing exists! I have been online dating off and on for about a year and a half now....

Laura asks: I'm relatively new to dating apps. Still navigating these waters mostly, but so far my experience seems to be pretty universal - some good date...

Missy asks: I'm a attractive, slim, college educated, decent job, well dressed (I.e. feminine not showy) confident and modern woman who can't get a second ...

What's the etiquette when you meet someone for the first time via an online dating website, and you can clearly see he or she is much heavier than the pictu...

Ah, yes. The "Who Pays?" question. But this time, we've put a little spin on it. The screen shots below are from an Instagram post announcing this episode of...

Cecilia asks: Hi Christan and Sarah! I've been dating a guy (he's 28) for the past ten months. It's my first "serious" ( or as serious as a 1 year relations...

Confused asks: Comment: Hi.  About 6 years ago I met a man online when I was living in NYC.  We went out twice and had sex on the 2nd date.  I was not emoti...

Niru asks: I have gone on several maybe 10+ of your speed dating events in Boston and have received only 1 match, which did not progress. At this point I am ...

What are some red flags when going out on dates? 1. Day of or last minute cancellations - I take this on a case by case basis. Sometimes people truly do have...