I'm shy

I like this guy and we're friends, but how do I ask him out on a date?


Cary Tennis
September 26, 2003 11:36PM (UTC)

Dear Cary,

It was early June and I had just gotten out of college for the summer and was back home in NYC hoping for some loving and laughs. Things took a different twist when I found out that my boyfriend was cheating on me. I was devastated and crushed.

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Out of four long-term relationships, three of the guys have cheated on me and that is always a bad feeling. So there I was in New York City, crushed and single. Then I met this guy. He was 27 years old and I am only 20, but then again I've dated guys who are eight years older than me, so it's not that far of a stretch in my book. This guy was just getting out of a very special relationship himself and had no wish to date anyone (which included me).

It's September now and we've gotten together a few random times over the summer and chatted about nothing in particular in e-mails and on the phone but it's gone nowhere. I think that I am falling for this guy hard and it scares me, because I have little reason to believe my love life is in calmer waters yet and I can't tell if he likes me.

All my life I've been shy when it comes to asking a guy out. I guess it has to do with my background (I've been raised in a fairly conservative family that believes it's the proper thing for the guy to ask.) This is 2003 but I still don't feel comfortable asking a guy out (people even say I'm demure). But I want to go out with this particular guy -- he seems to have everything I want/need -- and frankly I think I have a lot to offer him. So, should I chance it and ask him out or let the chance pass me by? I really don't want to risk losing a friend if he has no interest whatsoever. What do I do?

Alone and Single in NYC

Dear Alone and Single,

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Since you're 20 and came home for the summer, it would be reasonable to assume that you're returning to college just about now. So it wouldn't be very reasonable to get something started with this man just when you're leaving.

Of course, that's the reasonable me talking, the me who believes that we must find ways of not telling each other the bald truth because the bald truth makes people suddenly look across the room and see someone they must talk to about an investment or discover they have an urgent appointment or excuse themselves to go to the bar and order another round. The bald truth is upsetting and difficult but I dream of living in a world where bald truth is the currency our wallets are bulging with, where people treat every minute like a moment of ecstasy, where every word and gesture is a vapor trail bequeathed to their family and friends.

In that world, romantic and charged with urgency, you would tell this guy the truth and nothing but the truth. You would not be cautious. You would say: What is caution compared to the truth? You would say: I want to go out on a date with you. You would say, I think maybe I'm falling for you just a little bit. You would say, There's nothing to be afraid of, it's not like my falling for you is a weakness or a sin or some lapse of judgment; it's quite reasonable that I should be falling for you because you are the kind of man a woman like me falls for. You would tell him, There's no need to be embarrassed. It happens every day, it's just that nobody talks about it, or they talk to their friends instead of to the person they're falling for. So I have to go back to school but before I do I want to go out on a date with you and if it goes well and we fall in love I would like to have three children with you and live in a brownstone near Central Park but not too close to my parents. Do you have any genetic disorders I should know about?

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Cary Tennis

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