How Freaky Could You Act on a Date? (And Still Get Asked Out Again?)

During the show, he orders a pizza and offers me a slice. "I really dislike dairy farming, so I don't eat cheese, out of protest," I explain, shaking my head. He nods and takes a bite. I continue: "It makes me so sad, those poor cows, all captives!" I put my hands up to my face and drop my head. Completely freaked out, he says, "Are you OK?" I get up and, pretending to cry, walk away. I can't believe I'm pulling this off.

In the ladies' room, I splash water on my face to smear my eye makeup and head back to the table. The look on Nathan's face is priceless—he's frozen in terror. Poor guy. As soon as the show is over he announces, "I have to get up early tomorrow, so I need to head out." I laugh really hard—which makes him look scared for his life—and agree. Outside, he gives me a peck on the cheek and practically shoves me into a cab.

The next day when I tell him the truth, he actually sighs with relief. "I thought it may have been PMS at first," he explains. "But then I was on suicide watch!"

What I learned: OK, there's no need to act like a Stepford date when you're getting to know a guy—but there's definitely something to be said about keeping your cool.

"I talked about my ex all night"

Albertina Rizzo - 30

Bringing up past relationships when you're on a first date isn't usually considered a good idea, but tonight I'm going to find out just what kind of reaction you get for doing it (and doing it ad nauseam).

I'm at a neighborhood lounge with Kevin, a guy I met at a party. After the waitress takes our order, I say, "James always got that wine." He just smiles and asks how long I've been a writer, clearly trying to change the subject. "When James and I lived together, I worked for a fashion designer," I reply. "James encouraged me to consider writing comedy because he thought I was funny. That was three years ago."

His only comment is, "Which fashion designer?"

I tell him and then say that the long hours I had to work on that job were difficult on James. He tells me that he used to work a lot too, but now he makes a point to relax more. I respond by noting that if I hadn't worked so much, I'd probably be married by now. He looks at me like he's trying to figure out if I'm stubborn—or dense. Then he makes a break for the bathroom.

I refrain from mentioning James for most of the meal. Eventually, as we talk about our families, I tell him that I come from a long line of artists and that James does too, which is why we probably got along well. "I'm assuming James is not your brother," he says, looking exasperated. "God, no!" I say, a little too loudly. "Would I fool around with my brother?!" He laughs in the way you laugh at a crazy person, calls the waitress over and says, "Check, please." There are still a few bites of food on my plate, but apparently we're done here after less than an hour. He walks me home and says we should talk soon.

Here's the weird part. An hour later he texts me: "Had fun."

What I learned: When I come clean the next day and ask why he texted me, he says, "Guys will put up with all sorts of things if the girl is cute. Would I have put up with that for three dates? No. But I would at least give it a second try to a) see if you acted any better, and b) sleep with you." What can I say? I appreciate the dude's candor. From now on though, I'll spare dates the walk down memory lane.