There’s nothing quite like a first date. The rush of the unknown is hopelessly addicting. Each time I walk out my front door to go on one I wonder what blend of emotions will be swirling through my head when I walk back in. Will I be depressed? Will my nerves be dancing from a thirty-minute make out session? Will I be angry about something horribly insulting she said about Jews? Will I feel a testosterone-fueled sense of accomplishment from an unexpected, filthy dirty, drunken fuck in my car?
I’ve had countless first dates in my life. Some have been amazing, others God fucking awful. I’ve had incredible one night stands and swore they were the beginning of a steamy love affair, only to call and call but never hear from the girl again. I’ve unexpectedly met women’s parents on first dates, been farted on, had my keys thrown into the street, been called a faggot, had my asshole eaten out, puked on a girls shoes after eating a rancid oyster and had my favorite mustard sweater stolen. I still miss that fucking sweater.
So it surprises me that even after all that… I still come across scenarios that my first date playbook doesn’t have a counter move for. Enter Mandy: A thirty-year old publicist I met at a friends birthday party a few weeks back. 5’10, shoulder length brown hair, slightly broadened shoulders and one hell of a body. Her face totally reminded me of Lady Gaga.
Mandy was the only single girl at the party so I said fuck it and introduced myself. She spoke softly and the music was so fucking loud I literally couldn’t hear half of what she said… but of course constantly smiled, nodded and agreed as if I’d heard every single word.
There weren’t any sparks at all between Mandy and I the night we met. Through our twenty-minute conversation I struggled pretty damn hard to keep the conversation flowing. I’d ask her a question about herself, she’d politely answer, I’d quickly scramble to come up with another, and repeat. God I hate that.
She didn’t probe or try to find out anything about me and smiled at a few of my jokes, but generally seemed disinterested. It almost seemed as if she too couldn’t hear me and was playing along just as much as I was… either that or she just genuinely thought I was stupid. Because I felt stupid.
I took the pussy route by not getting her number that night and friend requested her the next day instead. Then, in a moment of boredom or maybe even slight desperation, wrote her a private message telling her how nice it was to meet her.
That’s when it got confusing.
Her response baffled me: Oh, hey! So glad you wrote 
Was wondering if I’d ever bump into you again. I had fun too! A little lou,d but fun. Hope to see you again?
Confused, I responded: Next Friday?
Sure!
I met Mandy at a rooftop bar in West Hollywood not expecting much. Curiosity about her enthusiasm in seeing me again had me more than anything else. She walked out of the elevator wearing a short white skirt, some dominatrix looking black shoes and a tight black top. Sexy as FUCK. She gave me light hug and was sure to not get too close.
I need to pause the action for a sec…
Look… I do OKAY financially. I can afford a decent apartment, a super low-end luxury car, I pay my bills on time and don’t really worry about my portion of the check when at a birthday dinner with friends. However, money is still a constant worry. I don’t save (who the hell does?) The unexpected $300 bill for lab tests after a check up (and that’s with medical insurance) or annual car registration send me spiraling into a pit of anxiousness where I freak out about my financial future, if I’m living above my means, if I should try to save more and complain about how food is now SO fucking expensive.
I don’t ever mind reaching into my back pocket and taking care of the check when taking a girl out. In fact, I enjoy being “the man”. I also always try to take my dates to decent bars or restaurants. I’m not twenty-five anymore. Pabst Blue Ribbon’s at dirty bars don’t cut it. And I assume it doesn’t cut it for most of the women I meet.
But I always wonder where being a gentleman crosses over into stupidity and being plain irresponsible. This train of thought started with our first two drinks, to the tune of $16.00 each, which of course had more yummy tasting stuff in them than liquor and almost immediately required a second round.
Forty minutes into the date and I was in no better of a position with Mandy than the night we met. I’m no genius, but I have enough insight to know when there isn’t any vibe. And by no vibe I’m talking about a date that consisted of me asking her a question, getting an answer, then sipping my drink or looking elsewhere for five to ten seconds while I tried to think of another.
It felt like a job interview for pussy. A job I definitely wasn’t getting.
I rarely find myself in such a shoulder shrug of a situation. My dates generally fall into one of three categories. 1.) Pretty good. 2.) Fucking amazing. Or 3.) Get me the FUCK out of here! Mandy and I weren’t having a bad time up there on that rooftop… but it definitely wasn’t a good time. The date almost felt like dinner with a client.
We ordered a third round and our waitress asked us if we wanted food. “I’ll look at the menu,” Mandy said. I wasn’t hungry but didn’t want to be rude and agreed to share two appetizers. Through my peppering of questions I learned that Mandy has been skydiving thirty-one times, bungee jumping twelve times, lived in a South American jungle for a month, climbed mountains in Peru, ate insects in China and is a lover of all things extreme.
The sense of adventure didn’t match her barely audible voice or lack of words. I only hoped there was a freak buried behind those Lady Gaga features. I seriously wondered if a girl like Mandy could be good for me and help me break out of my always-fearful, constantly neurotic Jewish shell. Or if she’s just a fucking loon.
As midnight approached we decided to leave. The check came. $149.27 not including the $20% tip. I paid it while wondering if I was a total moron for spending almost $180 dollars on a first date. Or if thinking that way made me a cheap bastard, or a plain bastard, or ungentlemanly. I wondered what else I could’ve done with her or what other guys do on first dates, and if I was doing way too much.
I walked Mandy downstairs, we gave each other a terribly light hug and she walked away uneventfully. I left and walked back into my apartment door… flat. Emotionless. Bland. All up until I got another facebook message from her at 12:46am: Hey! Thanks so much for taking me out! Had a great time. I hope we get to hang out soon
Maybe.
But I’m NOT jumping out of a fucking plane.
