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.

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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.

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"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".

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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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