Attractive men scare me, so I only date ugly ones

I would like to have sex with an attractive man -- but I babble like a moron at first sight!

Published October 30, 2008 10:15AM (EDT)

Dear Cary,

You probably get letters like this all the time, but I thought I'd ask anyway. I'm not a social retard: I have tons of friends and hobbies, and I'm happy with my career. People tell me all the time that I'm witty and really pretty, and over the years, plenty have expressed shock that I don't date ... at all.

The problem? I don't know how to talk to men I find attractive. Seriously. When I was younger, I never thought this was a problem, as everyone has social anxiety around attractive people, right? I only realized it was a problem a few years ago when I casually mentioned to a friend of mine that I'd never dated anyone I found attractive -- and had even been embarrassed to be seen in public with a few of the men I had dated (and it's not inexperience: I've had two miserable long-term relationships). Hell, I've never even slept with someone I found attractive. When she asked me why, I told her the truth: that since attractive men don't like me, I'd just gotten used to taking whatever's left over.

And so she said that I was cheating myself by being with unattractive men and made me promise that I would never date one again. I agreed and broke up with my then-boyfriend. Soon after, an attractive man asked me out. It was the only time in my life I went on a date with such a guy. Needless to say, it was a disaster: Since I really couldn't believe that he had actually asked me out, I acted like a retard and babbled relentlessly through the whole painful evening (and of course never heard from him again).

Because I've kept the promise, I haven't been on a date in almost three years now ... and I live in Manhattan. It's not that I don't know how to flirt. I flirt all the time with random people. It's not hard. But if an attractive man smiles at me, I immediately think he's smiling at me because he feels sorry for me (like, since I'm ugly, he'll brighten my day by smiling at me), or worse, if he talks to me, I always mess things up. A good example is that over the summer, I was in a class with a really hot guy. Because I knew how it would turn out, I tried ignoring him at first. Then he tried talking to me a few times, and even though I always dreamed of clever things to say to him, every time I saw him, I could never muster more than a one-word answer. He eventually stopped trying to talk to me. Toward the end of the class, after which I knew I'd never see him again, I tried talking to him a few times, but I always babbled incoherently and probably made him think I'm a retarded stalker, since he never seemed very interested in anything I had to say.

This is the story of my life; it's happened without fail every single time I've been confronted by an attractive guy, since I became interested in boys at around age 10 or so ... And I'm 31 now. Twenty years of misery regarding the opposite sex is too much to bear, and I definitely don't want to be single for the rest of my life. I definitely don't want to go back to dating ugly, dumb guys, but I'm still terrified of attractive men, even if I want to get to know them better, and even if they seem vaguely interested in me. I can't seem to adjust my way of thinking on this. Any suggestions for how to get my shit together? Many thanks in advance.

I'd Like to Date an Attractive Man, but My Brain Always Seems to Get in the Way

Dear Attractive-Man-Dater Wannabe,

What you need is a teleprompter. But teleprompters are too bulky.

Index cards are better. They fit in your purse.

Take some time to write down all your phrases on index cards.

Seriously. This will be so much fun.

Say the attractive man is in front of you and you are looking at him. If he starts to go away, say, "Wait!" Then go into your purse. Get out your stack of index cards.

On the first index card that you carry in your purse, held together by a rubber band, you will have written the following:

"These are my index cards." Read it out loud.

Take the cards out, take the rubber band off and read the next one: "Would you like to hear some of the phrases?"

He will look at you. That's OK. It's good if he is looking at you. Let him look. You don't even have to look at the attractive man. You can just look at the index cards. This relieves  the tension of looking directly at a person, and at the same time allows you to talk obliquely about the most direct and intimate of subjects.

Here are some more phrases:

"My friends say these index cards are just a crutch, and I agree."

"My name is ---------"

"Would you like to go out on a date with me this Wednesday night?"

"Feel my muscle."

"May I feel your muscle?"

You can arrange these cards in any way you like.

If he asks you a question, shuffle through your cards until you find a good answer. File them under subjects, like, "Acceptable replies to compliments about my physical attractiveness" and "Acceptable replies to the question, 'So, what do you do?'."

You will also need phrases you can use to initiate activities. For instance, you will want a file on "Ways to suggest we have a drink":

"Would you like to have a drink with me?" "Let's have a drink." "I'd like a drink, how about you?" "Do you know a good place around here where we could go and have a drink?" "What's your favorite drink?" "What's your favorite bar?" "Is your favorite bar nearby?"  "Would you like to go get drunk?" "Would you like to get smashed?" "Let's go get smashed." "Have you ever danced in a public fountain?" "Let's get a taxi and go to a bar I know." "Would you like to walk out of here with me on your arm and hail a taxi?"

Once in the taxi, you may need a small flashlight in your purse in order to read the index cards. Among the index cards you might want to use at this time are ones containing the addresses of various bars, instruction phrases for the cab driver, and things to say to the attractive man sitting next to you in the dark, such as, "Take your hand off my knee," or, "Put your hand on my knee," or, "Let's play Twister."

Just be sure to have plenty of index cards, indexed correctly for quick retrieval.

Eventually, after enough phrases have been exchanged, you may toss aside the index cards and begin speaking impromptu. When doing so, be sure to begin with simple phrases and work your way up to more complex utterances, keeping in mind at all times that though the man may be attractive, he has no greater power over you than any other man. He is simply a pretty face. Moreover, you have a distinct advantage.

He has no index cards. But you do.

Tongue-tied? Not a big fan of small talk? See p. 155:

("Whereas we are two free human beings freely choosing to associate in the manner that suits us both; and Whereas we feel confident that if we spend some time together we will, being each of us intellectually nimble, in due time find ample ground for conversation ...")

"Since You Asked," the best of Cary Tennis, signed first editions on sale now.

What? You want more advice?


By Cary Tennis

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