White Collar Criminal
Was this guy a Russian mobster?

Dating Disaster: Was He In The Mob?

My type, blue-collar younger guys, was not paying any dividends. So, while at Starbucks I decided to go against my better instincts and chat with a more uptown kind of guy. He joked that he was in the witness protection program. Though I wasn't sure it was right for me, we set up a date. But that was before Google informed me that he might have been joking about witness protection...

Dating Disaster: My Date With A (Former) Suicide Girl
This, unfortunately, was not my date.

Dating Disaster: My Date With A (Former) Suicide Girl

On a whim a few years ago, my friend Dave and I posted a YouTube video in which we invited women to double date us. In the months to follow, we would embark on over 200 double dates together, many of which would provide us with horror stories for our live comedy show. However, none were a bigger disappointment than one I experienced on my own.

Dating Disaster: He Froze My Account
He had her account frozen... how cold!

Dating Disaster: He Froze My Account

When I first started online dating after my divorce at age 39, I was terrified. Not because I hadn't been on a date in almost two decades. Not because I hadn't so much as brushed up against a man in over a year, let alone been intimate with one. And not because I was worried about inadvertently hooking up with a serial killer. What I was terrified of was that people I knew would see my online profile and think I was a desperate loser.

double date
A blind date with an ex. That's double trouble.

Dating Disaster: Double-Dating My Ex

First dates are a little dicey. Doubly so when it's a blind date. Make it a double date on top of it and you're talking about four times the dicey-ness. And, as far as dicey goes, it goes off the charts when it turns out that you know your friend's date. Know him very well.

drunk date
My date was drunk and actually pretty sad.

Dating Disaster: A Double Date Gets Double Drunk

It was a classic set-up, my friend's boyfriend's friend needed a date. The two guys showed up and were already a little boozy. My friend and her boyfriend sneaked off and I was left with a drunk fella. And then his vomiting. I decided not to move to the second phase of the date and somehow I was the bad guy...

Why Falling In Love Is Just Like Investing In Real Estate
What a precious investment...

Why Falling In Love Is Just Like Investing In Real Estate

In 2005, I briefly worked as a real estate agent in New York City, renting downtown luxury apartments to European pioneers, entitled college grads from Long Island, and investment bankers with trophy wives. The job, which I took merely as a means to support myself while pursuing more "noble" efforts as a rock musician, was truly f'ing miserable.

stolen ipod
My spend-the-night date stole my iPod.

Dating Disaster: Did You Steal My iPod?

Sometimes the seemingly perfect guy is up to no good. It starts with house parties, long phone calls and fancy dinners, but then it ends with a stolen iPod. No one said dating in Amman, Jordan was easy.

crying man
Whatever you do, do not cry on the first date, OK, man?

Dating Disaster: Stop Crying And Get Off My Porch

A first-time user of has a rough start of it. After drinking many, many beers, a first date becomes weirdly jealous, starts crying and refuses to leave her house. First dates and online dating rarely go this wrong.

ugly foot

Dating Disaster: He Had A Foot Fetish... With His Own Feet

Recently I went out with a friend of a friend. He was English. I mean, how bad could he be? But that was before he showed up, late and unshowered, and moved our date from a 5-star restaurant to a coffee shop. After making suggestive comments about my chest, he popped his feet into my lap and said to tickle away. Yes, these are the men I date.

police line

Dating Disaster: This Cop Wanted To Lick My Face

When I was living in NYC in early 2009 I met this cop from Queens at a jazz bar I used to sing in. I wasn't so sure if there was much of an attraction physically speaking but I was diggin' the whole cop thing. But a boring dinner gave way to some extreme pushiness, disparaging comments about my neighborhood and insults to my neighbor.

blue hand print

Halloween Heartbreak: I Painted Myself Blue To Get Him Back

For weeks, I'd been planning to dress as Smurfette. I couldn't admit to myself I only chose the costume because my ex-fling once mentioned it'd be cute. One of my summer dresses reminded him of the impish blue character. I never realistically thought he would come back to me. I wasn't even sure I wanted him to, but I did want him to regret his decision.

watch in a glass

Dating Disaster: I Was Really Late, He Was Really Drunk

The thought, "Oh God, he has to hate me," is never a good sign during a first date. But when you're two hours late and he hasn't responded to your last text, it's not possible to think of anything else. A set of circumstances conspired to make me late to a date and when I got there, my date had been drinking heavily, very heavily. What happens when chronic lateness and too much booze get in the way of really good thing.

No sign

Home-Schooled? Run Marathons? Sorry, You're Undateable

Ladies, I'd like to—need to, rather—introduce you to, a new blog that's slowly spewing out ludicrous and crass reasons for why men shouldn't date us. As if you didn't feel enough pressure coming at you from all angles to look, act and feel like the "ideal" woman that guys are looking for today, there's now someone telling the world that what you do with your food before you eat it will have an irreversibly negative impact on your dating life.

love, dating, home-schooled
My parents made me think about love differently.

Home-Schooling Gave Me An Unusual Perspective On Dating

When my friends reminisce about childhood days spent getting sent to the principal's office, or instigating playground drama, or going on awkward middle school dates to even-more-awkward middle school dances, I have nothing to share. I was home-schooled. Taking notes from Professor Mom, I learned more than the usual reading, writing and arithmetic. I memorized lessons in life and love. Lessons that directly influenced the way I approached dating.