Taking the leap on February 23, 1998…

Dear Breakup Girl,

I am a perfectly attractive, intelligent, successful, and talented young lady in my early 20s. I am also incredibly shy and so, I never got into the whole dating/relationship scene (yes, I am for real!). So I have a couple of questions: 1) Is it too late for me now, since everyone else has at least 7 or 8 years on me of experience? And does my delay mean there is something inherently wrong with me? 2) How do I go about it now that I’m out of the high school/college scene and working? I’ve just moved to a new city and know absolutely no one! and 3) is it even worth it after all the horror stories I keep hearing in your advice columns? These are three mysteries of life I’ve been pondering for a while now and can’t seem to find anyone else who can answer them.

— A Basket Case in C

Dear Basket Case,

You do realize, of course, that the people with all this “experience” are the same people with all the “horror stories.”

You’ll be fine.

Love,
Breakup Girl

A real go-getter from January 9, 1998…

Dear Breakup Girl,
I really like this guy — should I ask him out? Or should I wait until he does?
–Confused

Dear Confused,
There’s something to be said for waiting. Not because I think we should go back to the time when girls didn’t ask guys out, there were no women in Congress, etc. But because it’s fun to get asked out! It’s flattering! It’s thrilling! (Unless your suitor is that weird boy who wears shorts year-round, even in winter. You know the one.) And, more often than not, it’s useful — when he makes the first move, your preliminary guesswork is over: you know he’s interested, or at least “curious” (my term for one notch below “interested”).

But the same goes both ways. If you really want to be all you -go-girl about it, well then, you go, girl. Ask him out. Once. If he’s busy (or “busy”), you’ve at least made your point. Ball’s in his court now. You don’t have time to chase or flatter. You’ve got to work on that bid for Congress.
Love,
Breakup Girl