Generation Ex

My editor recently suggested that as long as I was writing something called "Singles," it might be helpful if I actually went out on a date every once in a while. Research. Give the column the ring of verisimilitude.

I must admit that I resisted at first. I’ve been on dates before. I know how they work. It’s basically a job interview over cosmopolitans and seared ahi. A bad date ends with a handshake or a restraining order. A good date ends up in the Styles section of The New York Times and the repopulation of the species is assured. Everything else is details.

I just started dating someone new over the holidays. We’ll call her Alison. Alison meets all the pertinent criteria (yes, she’s Jewish), and we are off to a wonderful start. Three weeks and still no restraining order. So far, so good. We are two happy little people, full of hope and promise, living on love. If history is any guide, this, too, shall pass. The repopulation of the entire Jewish population hangs in the balance.

Some people look at a first date through the impossible prism of "How would they be as my spouse?" This is not an unrealistic question to ask at a certain time in your life, at this hour of uncertainty, instant gratification, and mounting community pressure. But trying to determine — on the basis of a first impression — if this is someone I could spend the rest of my life with is a tough call. It’s a very high set of expectations to ask of a stranger when they open the door the first time you get together. You can’t just say, "Hi, nice to meet you. Will you be a really excellent mother to our children?"

I have a somewhat different paradigm. Not that I’m unaware of the long-term possibilities of meeting someone new. Anyone could be "the one," but that’s not the first thing that leaps to mind when we sit down to the "interview" part of the first date. I know, statistically, that most relationships don’t work out. It’s nobody’s fault. I’m not pointing fingers, but almost all of the dates you go on in the course of your life aren’t going to lead you to the altar. If things work out reasonably well, she might turn out to be your girlfriend for a little while, but after that, if you don’t walk the aisle, she’s going to be your ex-girlfriend forever. No rose-colored glasses here. When I go out on a first date, I want to know how she’s going to be as my ex-girlfriend.

These are people who have the capacity to bad-mouth you around town. You might even want to get back together with one of these people, so it’s a viable concern as to how one breaks up. Ideally, no one gets hurt in the process, but sometimes it can’t be avoided. There are some soon-to-be ex-girlfriends that you know, prebreakup, you will not be enjoying a good postbreakup relationship. In these unfortunate cases, the best thing is if you can make a clean break. Being cold and heartless actually serves everyone in the end.

I wanted to know the best way to be cold and heartless, so I called my friend Rob the talent agent, who’d just broken up with his on-again, off-again girlfriend. He told me things were already pretty rocky between them when she called him and they got into a fight. The rhetorical heat was rising when she finally pleaded with him: "What do you want me to do?"

"Are you on a cell phone?" he asked.

"Yes," she said.

"Press ‘end,’" he said.

I am a great ex-boyfriend, if I do say so myself. This is one area in which I am very accomplished. I’ve had tons of practice. You can’t swing a cat in this town without hitting one of my amicable exes. (This, sadly, is not a wonderful selling point when meeting someone new.) Usually, by the time we throw in the towel, the one thing we have in common is that we both agree she’s better off without me.

It’s still too early to say for sure, but, sadly, Alison doesn’t show a lot of good ex-girlfriend potential. She will probably not need a date for movie premieres, charity events or Lakers games. She will not call me late at night because she’s feeling lonely, and she doesn’t have a lot of sexy roommates to turn me on to. As an ex-girlfriend, she’s a total bust. It looks like we just might have to stay together.