My Most Unfortunate Dating Mishaps

A smart, funny, attractive guy who not only admits to being clueless about women but is willing to share his dating diary? Tap your inner Bridget Jones by offering him your advice.

As you all know, boys are really, really dumb. I always thought that it was good to be called a celebrity, no matter who it is. Obviously, I know Roseanne Barr and Star Jones don't go very far, but still, they are celebrities. I have never called a girl a celebrity that I knew was considered unattractive, but here are three of the stupidest ones I ever used:

JonBenet Ramsey — So, I was somewhat drunk for this one, and the long bathroom line didn't help, as I get somewhat antsy wanting to push the action. I approached the girl, and I just came out with it: "You look like JonBenet Ramsey." She looked at me in disgust, and her friend even stepped up to defend her.

"Um, she's dead."

"So is Marilyn Monroe, and you guys wouldn't mind if I used her to compare."

"She's a child."

"Okay, well, I mean, she was a model who was going to be hot."

Didn't work. My intentions were not bad, though. The girl I compared to JonBenet had way too much makeup on and her hair was poofed and teased all over the place. I thought if I called her JonBenet Ramsey it would be a nice way of saying that. Maybe I should have just stuck to: "You have too much hairspray in your hair and you're wearing too much makeup".

Cha Cha DiGregorio — One time in a bar I hunkered up to a girl's table and sat down across from her and said: "You look like someone from Grease." Her eyes lit up — this could only be a compliment, right? "Really? So, who do I look like?" "Cha Cha DiGregorio — you know, the one with the black-and-blue dress at the dance?" Oops, I called her the slutty girl. I did learn that even though a slutty girl might look hot, girls don't like to be compared to them. The girl didn't stay at the table very long after that.

Joan Rivers — My little sister's friend is somewhat loud and boisterous. Her face is kind of sharp and intense. One night we were out and I said: "You remind me of Joan Rivers." She looked like she was in shock. I was confused, because I thought Joan Rivers was hot when she was younger, and she was considered entertaining enough to interview celebs on the red carpet — a job that I've heard so many girls say they wish they had. Every time I see this friend now, she whimpers: "Do I really look like Joan Rivers?" I think to myself, You REMIND me of her, not LOOK like her. Never mind. You girls hold on to things way too long.

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