Dear ____ (you know who you are),
First off, starting a dinner date with a story about a condom slipping off and taking the girl to get Plan B is not a good opening anecdote, regardless of the fact that you told the story in the context of Aziz Ansari’s Netflix series, “Master of None.” You brought up Aziz and immediately segued into your uncomfortable story.
To be fair, it wasn’t the very first thing you said. First you shared that your parents want you to have an arranged marriage like your older brother, but that you aren’t having it. I asked if you’d seen Meet the Patels, the comedic documentary that follows the filmmaker in his attempt to make his traditional Indian parents happy by finding an Indian bride. You hadn’t, but you used that as a springboard to bring up Aziz and how you had your own slipped condom and Plan B experience just like he did in the first scene of the show.
I was willing to overlook that extremely awkward (and telling, as I’d later discover) story because I figured you were nervous, and I’ve certainly been guilty of oversharing on a date more than once. At least you liked Aziz and “Master of None”; that was some common ground.
Announcing that you’d shown my pictures to your friends was one thing (everyone does it, but who admits it?), but telling me that your roommate asked why you’d want to go out with someone my age stung. Considering that you’re over 30, I didn’t think the age difference was that big of a deal. Guys in their 20s routinely ask me out, presumably suffering from some kind of CWILF syndrome (which has necessitated inventing my own acronym – Childless Woman I’d Like to Fuck, since I’m no MILF).
So you weren’t smooth. That much was obvious. But smooth often equals sleazy, and at this point in my life, I’d rather find an awkward nice guy than a smooth player.
Clearly that’s my problem: I’m looking so hard for a nice guy that I see men I go out with through rose-colored glasses, viewing behavior that isn’t nice in the best possible light and misinterpreting it to make the man seem better than he is.
I was impressed when you told me you bought your parents in India a house. That is nice guy behavior. But most men do not treat women the way they treat their parents.
Let me backtrack a minute. When I showed up for dinner, I didn’t even think you were cute. Not that you didn’t look like your pictures – you did – but you were even skinnier than I imagined, scrawny in fact. You were wearing a hat in all of your pics, so I suspected you’d be balding, which I don’t really care about, but in person and hatless you had flying saucer ears that stuck straight out from your head. That being said, despite not finding you physically attractive, I went into the date determined to see the best in you, and I did, even when it wasn’t there.
Once we got past your multiple awkward overshares, the conversation flowed over dinner, along with the red wine. I was impressed when you told me your career history and how you’d come here from India by yourself at 24 determined to earn more and help your family. I liked your intelligence, sense of humor and the way we shared everything we ordered. By the time dinner was over, your positive attributes seemed to outweigh my initial lack of attraction.
When you suggested we go play pool after dinner, I admitted that I didn’t know how, having played one game of pool in the entirety of my life, during grad school. You offered to teach me. There is almost nothing more attractive than a man who can patiently and kindly teach me something I don’t know, so I agreed. You were a patient and kind teacher, though the way you kept adjusting my position by shoving my ass around was, again, less than smooth. Not to mention that in the car on the way to the pool hall, you asked if I watch “The Big Bang Theory” and told me I look like Mayam Bialik. “Like Blossom?” I responded, insulted, but you were too young to remember Blossom. “It’s my schnoz,” I said. “It’s a compliment,” you clarified. But was it?
I was practically the only girl out of my immediate high school friend group not to get a nose job, and my mom always told me I had a “Roman nose,” which is somehow classier and more attractive than a Jewish nose.
We had a cocktail while we were playing pool, and at some point you leaned over and started kissing me, and you were a good kisser. We made out right in the middle of the too brightly lit pool hall with plenty of people watching us, but I didn’t care. You got all your balls in way before I did and then let me finish out my game just to practice.
When I asked if you thought there was any chance I could get good at pool, you said it would take 30 games. That seemed honest, and a lot less daunting than Malcolm Gladwell’s 10,000-hour rule. Thirty games of pool was doable, especially if you were going to keep teaching me.
You invited me to come back to your place, just a few minutes from our present location. I had consciously chosen to drive all the way out to Manhattan Beach from Santa Monica to meet you rather than take a Lyft so that I would have no excuse to drink too much and make bad choices. I’d already gone beyond my usual two-drink driving limit, but with all the Italian food we’d eaten I could have driven home just fine at that point.
I told you I didn’t think that was a good idea, and this is when I overshared, going into my typical spiel about guys never calling again after you go home with them right away. That is something I never need to say to another man as long as I live – I just need to not do it. You – like every other guy who has ever tried to get me to go beyond my intended boundaries – assured me that I was going to see you again.
“Do you like Indian food?” you asked. Of course I like Indian food. “Are you free on Wednesday?” I was. “I’m going to come over and make you chicken curry masala,” you promised.
It was an appealing offer, but I’ve been lied to too many times to believe you that easily. Remember my admonition – Ladies, believe NOTHING men say on a first date.
You then upped the ante in a completely original way.
“I’ll give you $100,” you said, “and you can give it back to me on Wednesday when I see you.”
Were you for real?
By this point we were having our second cocktail. Agreeing to order that drink, I’d already taken a step in the wrong direction from my intended plan of driving home, which would take half an hour with no traffic.
“Is there an ATM in here?” you asked the bartender.
He pointed you in the right direction and you withdrew $100 and handed it to me.
So you were really putting your money where your mouth is.
Still, I was hesitant.
“Even if I do come over, I’m not going to have sex with you,” I said. My descent down the slippery slope had officially begun.
You assured me that was fine.
I was half a bottle of wine and two vodka sodas in, not to mention tired, and driving all the way back to Santa Monica was sounding less and less appealing.
But if I was going to spend the night, there was the matter of coffee.
“Do you have coffee at your place?”
You assured me you did, from Trader Joe’s. No, it wasn’t French roast, but most Trader Joe’s coffee is drinkable.
“What about half and half?”
This would be the deciding factor for me.*
You admitted that you had no half and half, but promised you’d go out and get it in the morning. There was a Trader Joe’s practically across the street from your place.
Hundred dollars in hand, assured my caffeine and cream needs would be met in the morning, I agreed to go back to your place.
I was still determined not to have sex with you. We could just sleep together.
How many times has that been a winning plan?
*I need my coffee with half and half and sugar, preferably brown sugar, and am so militant about making sure I will have half and half in the morning that it has caused fights with my family when we were returning from vacation together and being picked up at JFK to drive back to my sister’s house in Connecticut. No one was willing to stop for half and half on the way home, just because it was late at night and we’d just flown back from Belize. I was also informed by one of my close girlfriends when we were on vacation in New Orleans that my perceived request that she bring me half and half when she went out in the morning when I would still be sleeping was delivered more like an obnoxious demand, feedback that I took to heart.