But uncertainty makes people uncomfortable; it turns us into babbling, oversensitive neurotics. A prime example: my friend Casey Ireland, a 26-year-old PhD candidate in English. Casey is smart, funny, and super cute, yet most of her dating life thus far has been like a performance art piece of How to Lose a Guy in 10 Minutes.

“I’ve never been great at getting people to like me,” Casey told me, melodramatically sipping Champagne at the Jane Hotel. “Basically, for years, I wanted every first date to be my last first date. I went in thinking, ‘Maybe this will just be it for a while, and I won’t have to keep putting myself out there for other people to evaluate, and I’ll just be accepted and loved and blah blah.’ I once ended a first date by asking a guy, Where is this going?” In summation, it’s hard to make desperation look cute.

To combat her insecurities, Casey developed a plan of action. “The date strategy I employed many times,” she told me, “was to try to get the person to reveal personal things to me, in order to make them feel vulnerable. I understand that’s manipulative, but I already felt so vulnerable in the situation of a first date—I just always felt like the guys I was with were inherently cooler than I was—so I had to figure out a way to minimize their power over me. So I’d be like, ‘How’s your relationship with your mom?’ and then once they were two martinis deep and spilling their guts to me, they’d be like, ‘Wow, I never say this stuff to anyone!’”

I asked Casey the million-dollar question: Did that strategy actually work? “Absolutely not,” she said. “My strategy was a just defense mechanism. It had nothing to do with actually getting to know somebody or feeling comfortable. It was about compensating for an inherent lack of self worth.”

Unfortunately, I can relate to that. For a long time I destroyed first dates with my pathological need to be wanted. Case in point, a recent date I went on with a TV writer. We met for drinks, and it was clear from the beginning that the guy wasn’t super into it. This, of course, triggered my dating survival instinct. I entered into a competitive robot mode where the mission became simply to win the date—to make this guy want to fuck me. Perhaps I was the victim of some very effective negging, à la The Game. Or maybe the guy just didn’t like me. Either way, why was I fighting for someone who I hadn’t even connected with? Sometimes, it’s easy to become so concerned with not being rejected that we forget to step back and assess whether we even like the person.

As of late, I’ve been trying to bring the most Charlie Rose version of myself to dates. To chill, sit back, and ask good questions. Not in a manic, manipulative way. But in an attempt to work out: Are you special enough for me to share myself and my feelings and my ideas with you? (Basically, are you cool, or nah?) Rather than busting in like a sex maniac starving for dick and attention, I’m trying to be more present in the moment. I’m not saying that you shouldn’t sleep with someone on a first date, if it feels right. But the goal should be to go in without preconceived notions or an agenda, and just feel it out; to just be yourself, only better—and less desperate.

Hair: Takashi Yusa

Makeup: Mariko Hirano

