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Confessions Of A Serial Dater


One woman who’s been on many dates reveals her hard-earned wisdom—and whether you should try stepping out so much, too.

By Amy DeZellar

here we were, sitting across from each other, on what I’d soon find out would be our last date. “I don’t think I can keep dating you,” he said. It’s not that he didn’t like me or that he’d started seeing someone else. No, the problem was that he’d recently found out I was on a mission: to go on fifty dates and write about my experiences. He, for example, was date #13. I had 37 more dates to go.

“Do you realize how many ‘So what kind of music do you listen to?’ conversations that
Serial dating is not inherently good or bad on its own; it just depends upon how you use it.
is?” he pointed out. “I couldn’t do it.” What he means is that he wouldn’t do it. That’s because he is not one of us. He, unlike me, is not a serial dater.

Serial daters measure their relationships in weeks or months instead of years. We dance around exclusivity or submit to it reluctantly. We believed our grandmothers when they told us that dates are like buses: If you miss one, there will be another along in 15 minutes. We are a high-spirited bunch, and nothing if not thorough—Match.com, social clubs, happy hour at the neighborhood hot spot, We do not settle for the first person who comes along and seems OK; we revel in the search. We are ever aware of all the delicious options out there… somewhere.

Much like power or credit cards, serial dating is not inherently good or bad on its own. It just depends upon how you use it. Many people I’ve met could stand to benefit greatly by adopting our “more is more” mindset. But at the same time, there are just as many who go overboard and may want to stop the insanity already. Want to know if you fit into the former or latter category? Take a look at these two checklists below and see which strikes a chord.

You should try serial dating if...

1. You’re a woman. Dating a variety of prospects and not getting attached too quickly is stereotypically the realm of men. It’s counterintuitive but freeing as hell for a female to view dating like the Testosterone League does. Men treat stuff like business and romance as a competitive sport. Maybe that’s why they have more fun with them.

2. You have so few dates you view each one as crucial. If you haven’t had a date since the Cenozoic Era, of course when you finally do get one, it will be too big a deal. If you date every week, it will snap things back into perspective. It’s the difference between agonizing about what to wear two Fridays from now and having a date “uniform” already picked out.

3. You find yourself trying to force things to work with someone who isn’t right for you. In economics, it’s
It’s an established law of nature that the more admirers you have, the more you attract.
called the point of diminishing returns. You’re putting in a lot of sweet, sweet time and effort and getting a paltry return on your love-life investment and wow, is it is making you bitter. Maybe the person you’re dating isn’t that crazy about you, but you’re just making things so damn easy that he or she sticks around. I bet you’d give that slacker the heave-ho if you had other cuties to compare him or her to.

4. You want to feel more attractive. Like Scarlett O’Hara… or Wilt Chamberlain. It’s an established law of nature that the more admirers you have, the more you attract. Maybe it’s because the smell of desperation is off you. Maybe it’s because people just want what everyone else wants. Whatever the reason, dates beget dates, which is great for your ego.

5. One rejection makes you want to hibernate in the frozen dessert aisle for the winter. “I wish I had a more casual attitude toward dating,” said my friend S, a 40-something Emma Thompson type. “If I talk to a man I don’t know and he isn’t instantly receptive, I’m afraid to try again with someone else for six months.” Odds are that the more people you meet, the more who’ll accept as well as reject you. You’ll see any one rejection as a minor blip rather than as earth-shattering.

You might want to stop serial dating if…

1. You’re always holding off on committing because you think you can do better. I often meet serial daters with unrealistic expectations: If you’re an average Joe or Joanne and you manage to swing a date with an underwear model, does he or she really have to be a Ph.D., too? Granted, these gems may be out there. But if you’ve been dating for twenty years without landing one and are scratching your head, then it may be time to visit the Reality Fairy.

2. You realize you’re mentally planning tomorrow night’s date while you’re still on this one. Being present mentally as well as physically during drinks and dinner is pretty much a minimum requirement if you’re trying to get to know someone. Taking cell phone calls, text messages, or emails from other prospects while you’re on a date is not only rude, it also probably means you’re overextending yourself.

3. You’re trying to rack up as many dates as possible and don’t care who you’re with anymore. Common wisdom would say that women may do this to feel like the belle of the ball; men may do it to get laid. And while that’s fine provided the people you’re going out with are on board, after a while, you may well be missing the trees for the forest. Regardless of your motives, each date should at least be memorable and enjoyable rather than merely like a notch in your belt. Counting’s for kids.

4. You’re starting to recycle prospects without remembering them. I met a man at a party who wanted to go on a date with me. Only thing is, we’d already gone on a date 18 months earlier, and he didn’t even remember! Since even in my serial-dating haze, I did recall that we didn’t hit it off the first time, I declined his offer for a second date.

5. People with commitment in mind never call for a second date because they can tell from one date that you’re not settling down any time soon. If pressed, they will say things by way of explanation like “You don’t seem to know what you want.” The truth is, they are well aware of what you want: your next date… and you don’t care whether or not it’s with them.

Sure, there can be a time and place in your life to try serial dating… and a time to put down the Palm Pilot and realize that anything — even meeting a fascinating new person every night — gets old after a while. Take it from me: By the time I was on my 50th date, I was feeling a lot like my date #13 did when I met him. I was ready for the real thing. And that’s exactly what I found. Eventually.


Amy DeZellar is the author of Dating Amy: 50 True Confessions of a Serial Dater.
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