This story is from a while back, maybe two or three years ago at this point. But, seeing as how I was single then and single now, Jewish with an Italian last name then and now, and attracted to women then and now, I’m pretty sure it still applies.
For me, the hardest part about picking up a girl has always been the approach and the close. The middle, I’m great at. I can keep a conversation going (even if it’s to entertain myself) for a while. But the conversation starter and the number-ask portion of the night I struggle with. I’m not sure why, but the following is an example of this.
It was early December, maybe even late November. I remember that because a former professor of mine (who also happens to be Jewish) had asked me to go to a singles event hosted by a temple he belonged to in New York City.
Not so keen on the idea of attending a Jewish singles event with a professor I used to have (Granted, he and I are/were friends so it wasn’t anything specific about him or the event even, just a general feeling I had), I told him that he should let me know when the next one was, figuring that since they were usually on or around Jewish holidays and I couldn’t think of any that were going on, I was pretty much in the clear.
Proof I’m not a very good Jew: Hanukah was actually in a week. How I forgot about the only actually fun holiday on the Jewish calendar is beyond my comprehension. As you’d imagine, I couldn’t say no and in a week’s time I found myself ducking into the downstairs, reserved section of a bar on the Upper West side.
It’s not fair, but I had certain preconceived notions about what I might encounter as I got there. Can you honestly blame me for being worried that this party would be a very lame, overly religious herb-fest? I had no idea what to expect in any of the following areas:
- Age of attendees (I was 22, my professor in his mid-40s I believe, so the range was totally up in the air)
- Attractiveness (but that can be said for any bar in America)
- Amount of females in attendance
- Amount of potential religious fervor (It should be noted that I am Jewish, but more culturally so than in the “go to temple, if even just on high holidays” way of thinking so I was a little uncomfortable around potentially being surrounded by people that would expose me as a phony)
- Music (Were we talking about a ton of Matisyahu? When did he shave? Why did he shave? Does he look stranger shaved or unshaved? So many questions, so few answers.)
Right off the bat, the music question was answered. 50 Cent’s “In da Club” was blasting so loud from the basement bar that I could hear it as I came through the street level entrance.* The next issue to get dealt with was number 4.
Before I could enter the party, I had to sign in. As I’ve said, I felt funny being at this event because not only did I not belong to this specific temple, but I never went to the one my family actually belonged to. I’m not saying that to be cool or flip, just honest. I haven’t gone much and felt really weird about signing in at this event with a last name like Spinelli. I could’ve sworn the ink in my pen was red as I wrote Spinelli below a list a mile long of Bergs, Steins and Felds. I half-expected the woman at the sign-in desk to brand me with one of those cattle prods, to let people know there was an impostor among them.
The rest of the concerns I had came into focus as I walked into the party and met my friend. There were a decent number of women there, ranging with pretty fair variety in age and attractiveness. The one girl that was probably the most attractive, predictably, had about four men talking to her every time I took a gander in her direction.
Instead of working up the courage to blow them out of the water and impress her with my wit and charm, I decided it would be more fun to chat with my friend and talk to other, less attractive (read: less threatening, less nervewracking) women. Of these chats, one sticks out. It went something like this:
Woman: “How come I never see you at services at the temple?”
Me: “You know, I’m just not in the city that often.”
Friend: “Scott, don’t you work in the city?”
Me: “You know what, that’s a good point, I do work in the city. I’m actually working in the city 5 days a week. I forgot that.”
Silence.
Me: “I think I have to take this phone call.”
Okay, so maybe I’m not so great at lying. Or, maybe my friend is just awful at it. Either way, the night continued on and somehow I wound up getting a drink by myself at the bar (even my professorial friend had found himself a nice single gal to talk to) when that good looking girl I mentioned from before found her way over to me.
She actually stood next to me waiting for a drink for about 5 minutes before I finally mustered up the courage to say something. I think I said, “Hello”, though it could just as well have been “Hey”. She responded in kind with something reciprocal and off we went. Before I knew it we’re laughing and joking around, tossing blue and white jelly beans (Israel colors, what what!) into one another’s mouths. It was a wild time.
So, now thirty minutes into our chat, she gets up from the table we had sat down at and looks as if she’s ready to leave. Well, that’s probably not right. She didn’t look like she was going to leave, she actually said I’m going to get going, so it wasn’t so much a look as a fact. Most men would’ve said something substantive. I said nothing other than “Okay.”
The look that came over her face was a combination of pity, sadness (at how pathetic I was), and annoyance. She hung around for another minute, awkwardly, giving me another chance to say something and when I didn’t, she turned to leave but before she did, she stopped herself. Righting her body towards mine again, she said, “Aren’t you going to ask me out?”
I was floored by this. Of course, I had thought about it. I wanted to, I just was paralyzed by fear (of rejection, I suppose, though in fairness I knew she’d say yes) and figured it wasn’t that big of a deal if I never saw her again so why even bother asking.
“I mean, I had thought about it,” I said without a trace of irony. “I just wasn’t sure what to say.”
“How about… would you like to get a drink or dinner some time?”
“Yeah, that sounds nice.”
“No, you idiot, you ask me that.”
And so I did. And she said no.
Kidding, she said yes.
We wound up only going on one or two less-than-thrilling dates and if I can say I learned anything from it, I can say that it’s always best to give things a shot (like, say, a Jewish singles event with a friend nearly twice your age or just having the courage to ask a girl out) because worst-case scenario, you’ll at least have a decent story to tell.
*Completely off topic, but if you’re a fan of 50’s and long for the time when he was actually worth listening to, check out this and this.
scott spinelli 
I knew this story and still laughed. Out loud.