How to Be Totally Inappropriate on a First Date

First dates are like auditions. I love auditions. I also love job interviews. And doctor’s appointments. Basically anything that requires me to funnel all of my charm and personality into a scheduled interval. I’m also happy to answer questions about what medication I’m taking and whether or not I’ve had an epileptic seizure in the past year because I’m just that keen to talk about myself.

Not that a first date is all about me. It’s about you too. So, what do you think of me?

But really, I’m a good dater. I listen, ask opened-ended questions, and my penetrative conversational skills can fill any void. Are you turned on yet?

Don’t be. There’s one problem.

Think for a moment about your deepest insecurity, your hot button issue, the source of your vulnerability. Know what it is? Now imagine some chick you met on OkCupid zeroing in on it within the first five minutes of your innocent coffee date. Like, “Gorgeous day don’t you think? My, this latte is overpriced. So, I feel like you might have a family member in jail, do you?”


OK, I’ve never said that. But on a scale of inappropriateness—let’s call it a scale of Amanda Bynes to Queen Elizabeth well, just call me Kanye West.

Let’s start with the Astrophysicist. For some reason, she felt uncomfortable with her intellect. I didn’t know this right away; it came clear weeks later when I commented that I could only be friends with smart people and she got this look like a seasick sunday school teacher and informed me that intelligence played no role in her friendships. Keep in mind she’s saying this at a dinner party full of baby astrophysicists, all of whom kept making jokes with punch lines like “Cold object radio waves,” at which point everyone would laugh like really intelligent hyenas and I would clear my throat and smile.  But that was all much later.

On our first date, we meet at a coffee shop in Pasadena. I have no idea she’s getting her phD but I know she goes to a school called Caltech and for some reason, I assume it’s a technical college, like a trade school. So we’re talking, and she mentions doing her undergrad work at Princeton.

“Oh,” I say, “so you’re doing grad work now?”

“I’m getting my phD.” She says it like she’s admitting to a childhood spent strangling kittens.

“In what?” I ask.


I laugh because seriously, what’s funnier than astrophysics? (Rabbis. Rabbis are funnier than astrophysics. And the word “adjacent” when used in an unexpected context.) And suddenly, I realize where I’ve heard the name Caltech before—in an article on the top schools for scientists. It’s all starting to come together.

“Oh,” I say, “You must be smart.” Then I excuse myself to pee.


I do a lot of peeing on first dates. Nerves, I guess. Or possibly the fact that I never stop drinking water. I like to do this trick where I drink water while peeing, as if it’s going right through me. But the only person who’s ever seen me do it is my sister because I’m a lady. Where was I?

Right, next date. The Texas Oil Baby. We meet for—you guessed it—coffee. This time at a Starbucks in Chicago. Turns out we both attend the same incredibly expensive school. I start in right away about how I’ll never pay off my loans and I might as well find a nice paper bag to live in. Then I go into my bit about how my degrees in women’s studies and creative writing have prepared me for a life in food service and she’s laughing along and without really thinking about it

I say “How did you pay for school?” Now, let me pause here to note that I’m incredibly blunt about money. I’m constantly asking people how much they make, what kind of rent they pay, the cost of their car, their clothes, their sunglasses. Because I’m curious, I guess. But also because I’m kind of an alien when it comes to money. I’m an alien about a lot of things, actually. Not like I came to this country illegally, but like I came to this planet an hour ago. For example, yesterday I had a conversation with a friend about his rug. How did he know he needed a rug? I asked. How had he chosen it? Where had he bought it? Was it a quick decision or did he plan for it? How did he decide what he was willing to pay? I went on for five minutes while he stared.

“Haven’t you ever bought a rug?” he asked, finally.

No, no I haven’t. I’ve never bought anything, really. Just clothes. Wait, once I bought two plates with rainbows ringing their circumference. I really should own a couch or something but whenever I think about investing in housewares I imagine just how much sushi I could buy instead.

Where was I? My date with the Texas Oil Baby.

So, “How did you pay for school?” I ask.

“Um, cash,” she says and looks away.


“You paid cash for college?” I’m getting louder because I’m remembering how her OkCupid profile claimed she made more than 100,000 a year and I thought she was joking but…

“Oh, I say, “You must be rich.” Then I excuse myself to pee.

I’m in the dating game again now, and I’m wondering if I should invest in a warning label (“Don’t worry Astrophysicist, Ima let you finish, but first let me make you feel insecure.”) or a siren (Internal and triggered whenever I start to open my mouth.). Of course neither of the examples I mentioned are mean-spirited, but both honed directly in on my dates’ insecurities. Perhaps I shouldn’t worry; clearly this tendency hasn’t interfered with my social life. I’m always asked on a second date. But maybe that’s because people like being called out, feeling known and uncomfortable, feeling seen. Or maybe I’m just that hot.