What are the principles governing dating? How have the “rules” been amended? Two letters from people seeking to form more perfect unions.

Dear Breakup Girl,

I’m in the process of ending a four-year relationship (ten years together overall). Due to severe heartache, I’m not looking for a more serious relationship. However, should there be an occasion where I agree to date someone from time to time, I’d like to know the “rules” of the game. It’s been a long time since I’ve been in the dating scene. What are the rules these days? Are women supposed to let men make the first move/call/email? Are women supposed to play hard to get? Dating was much different when I was 18!

— Joy

Dear Breakup Girl,

I’ve been divorced one year, and I’m totally confused about “dating in the 90s.” (I’m bald, average looks, late 40s, overweight.) I don’t know what is expected of men today. Do you have any advice on: meeting single women, asking them out, phone calls, dinner, movies, cards or flowers, kissing, sex, week-end trips, over-nighters, and looks?

— Lost in the Midwest

Dear Joy and Lost,

I’ve said it before, I’ll say it again: things used to be so simple. Boy met girl, boy dated girl, boy proposed to girl, boy and girl settled in Stepford. I know, there were no women in Congress and birth control was illegal, but hey, at least when it came to dating, you knew what to do. But no more. Girl meets boy at Gender-Bender Night at Click & Drag, girl hacks her way into the FBI server to do a background check, girl wonders how long she needs to wait before inviting boy to her home page.

So the answer, you guys — and this is not a cop-out — is that there really aren’t any “rules” anymore. At least none based on gender. Look, everyone’s as clueless as everyone else, and everyone’s different. There’s no point in trying to adapt arbitrarily to this thing called “the rules of the 90s — what if your intended follows “the rules of the 40s?” Seriously. As far as Breakup Girl is concerned, there are really only four “rules” today: (1) be nice; (2) take “no” for an answer; (3) whoever invited pays; (4) no dates at “Hooters.” Other than that, do what feels comfortable for you (however “comfortable” it is to put your heart on your sleeve and your pride on the line). That is always what’s going to give the best, most sincere impression.

Love,
Breakup Girl

P.S. Oh, advice on movies. “Good Will Hunting” rocks.

Originally published February 9, 1998