Quitting While You're Ahead
by The Dating Diva
November 3, 2000

This is why Las Vegas casinos make so much money: gamblers don't know when to stop. No one ever says to themselves: "When I make $100 I'm going to walk out." No, they make $100 and they think, "I can make more" -- and so they keep gambling.

On the other hand, people often tell themselves: "If I lose $100, I'll stop." Cutting your losses seems to make sense to everyone.

But if you only devise rules for when you're failing you'll never get anywhere. You also have to have a top point, the point at which you've won enough to leave. That way, you're much more likely to walk out of that game of 21 with $100, as opposed to what usually happens: you make it all the way up to $500, and then lose it all again, before leaving a hundred in the hole. Feeling virtuous, of course, because you stopped just when you said you would.

And that's why few people leave a winner -- the only rule they have is to walk out of the casino when they're down. Ridiculous. You've got to learn to quit while you're ahead. It will serve you well gambling, we've all heard it's the way to end a stand-up comedy routine (start with you second-best joke, but end with your very best and "leave ‘em laughing"), and it's going to serve you well in dating too.

Everyone I know has a story -- and usually ten stories -- of a date that was just lovely until the other person pushed it too far. Women, especially, have all regularly blackballed a guy when a meltingly-perfect first kiss turned into his trying to see how much play he could get over the handbrake. (Speaking of which, kisses should never take place over the handbrake anyway -- get out of the car and walk her to the front door.)

It's as if there's some high school mentality still at work in too many men's minds. "Wow, there's a female letting me touch her, and who knows when that's going to happen again so I better get as much out of it as I can." But that kind of push is the surest way to bring the whole roll in the hay to a screeching halt. You might get a little more on that given night, but there's going to be a little pit in her stomach which is totally turned off. And that feeling will grow -- either until she learns to trust you and it goes away or, more likely, until she decides she just doesn't like you anyway. You should stop long before she has to tell you to. One long, langorous kiss and then skedaddle. Trust me that's going to get you laid much faster than pushing for it.

And it's not just sex. Quitting while you're ahead is also important when you're interested in someone who's confused about you. They knows you like them, they've said they're not sure what they want to do -- your job is to drop the subject, continue to be attentive, but regularly be the first person to walk away. The only way the other person can come around is if they have room enough to think . . . so they can realize that when you're not putting active pressure on them you're a damn fun person to be around. So talk to them at parties, go out with them occasionally, but don't hang on them. No pushing. Leave ‘em laughing and walk away.

Consider the opposite of quitting while you're ahead. The basic alternative wooing plan is to pay someone so much attention that they tell you to stop. Or at least that they wish you would. Not the kind of impression you want to make.

Note, do not use this whole "quitting while you're ahead" theory as an excuse to never try anything. I am not saying don't take any chances for fear of getting rejected. I am merely saying that when you know you've got their attention -- you know they're laughing with you, or that they're knees just buckled -- that's the perfect time to exit.

That's the last memory they'll hold, and it will make them all the more eager to see you again. They won't be able to stop thinking about you. Total preoccupation with your next date -- that's the power of quitting ahead.

And while you're at it. . . try it out at the casino too.