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Dating Roulette

What happens when a generally sane woman attempts to go on six blind dates in two weeks

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Being single is awesome most of the time. You wake up and go to sleep when you want to. You can have cereal for dinner and nobody complains. If you forget to pay the electric bill, the only person to have an argument with is yourself. Toilet seat up or down? Not my problem! Unless you have a pet that you're trying to keep alive, nobody cares if or when you come home.

But — in addition to the ever-present fear of dying alone — being single means you can develop some pretty bad habits, since you only answer to yourself. These habits might include canceling dates at the very last minute because you can't stomach the idea of sitting through another boring dinner with a stranger, but readily reigniting an affair with your old married lover. Or more innocuous things, like leaving your favorite earrings on a one-night stand's nightstand, and accidentally hitting on your former co-worker's son.

My friend Evie and I recently found ourselves in similar situations. We're both 35 and divorced, and we have some bad habits that need to be broken. Our coupled friends Stella and Holly proposed a master plan to break us of our wayward ways, and possibly produce a good catch for both of us: Evie and I would each go on six arranged dates, all selected by our friends, within a two-week period, in the hopes that just one of the six shots would hit the mark. We were skeptical, but ... game on!

My first date was engineered through my friend Jane. After a seven-hour conversation with Bachelor No. 1, in which we discussed everything from Freddie Mercury's best unitard to Tennessee legislation, I felt like we were comfortably in the Friend Zone. One down, five to go.

Bachelor No. 2 came from Evie, who hosted a dinner party with a bunch of couples, and us. Naturally, No. 2 and I sat next to each other so we wouldn't infect the rest of the happy couples at the table with our singleness. I'm not sure what I did or said that night, but after knowing him for only a few hours, he was asking how many children I wanted and how I felt about living on his farm. Next!

Holly procured Bachelor No. 3, whom I approved in advance after seeing a photo of him on her phone. I met him for drinks one night, and in our getting-to-know-you banter, I noticed that I was asking the majority of the questions. He seemed a little detached, and I couldn't gauge his interest. So we drank more. Then there was dancing in honky-tonks. More drinking. Bad dancing. More foot-stepping than two-stepping. We discovered we were better at making out than talking, so one thing led to another, as it does.

Still, I couldn't read No. 3. I sensed that I wasn't his type, and I wasn't really sure if he was mine. After a couple more dates — or hangs, or hookups, or whatever it is we call these things nowadays — I realized I was always the one reaching out to him, and he wasn't really making an effort with me.

One afternoon I casually texted him to see if he wanted to meet up that night, and he responded that he couldn't go out because he had to get up early the next day to buy the new iPhone. I took that as an extremely polite blowoff — so that's the last time he heard from me. I mean, I was on a deadline.

Noticing that I'd already blown our two-week target, I checked in with Evie, who hadn't even gone on one date yet. At first I felt victorious, but then I realized that all I'd managed to do was fire a bunch of blanks. Nobody won this game.

But being forced to date under the gun also forced me to be much more selective about who I spend my time with, even if just for a couple of weeks. I also avoided a lot of bad habits I'd exhibited in previous relationships. When someone didn't show interest in me, I shook it off and moved on instead of desperately vying for his attention. When someone said they loved me — even if he was a little drunk — I politely rebuffed it instead of playing along in order to avoid hurting his feelings. When I suspected that I might not fit into someone else's mold, I didn't contort myself to suit his wants or his needs.

Is it possible to carry such newfound knowledge into future relationships, dates, hangs or hookups? Who knows. They say old habits die hard, but maybe you just have to be ready to pull the trigger.

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