Lessons Learned

First Date

Pre-date Makeout

Everyone's absurd and ridiculous dating life has to start somewhere. The summer after I graduated college, my good college friend, Stephen, came back to New York to visit friends and family. Per the usual craziness, it was a 'must go out' evening. My college girlfriends and I met him and his boys out on the town.

Several bottles of vodka later...I found myself making out in the corner with his friend Mark*. Mark aggressively and unsuccessfully tried to get me to go home with him, but got my number instead. Several text messages later, Mark and I were going on our first date.

Pre-date

It was a hot, soupy summer night. I was so nervous; it was my first real date! He suggested going to Supper, which my friends had raved about, so I was looking forward to it. These same brilliant, wonderful friends, also suggested I have a glass of wine before my date, to calm the nerves. So I poured myself a glass (big enough to hold about a half bottle of wine) as I slipped on my adorable, purple Ella Moss dress.


Mark had suggested to first meet at his apartment, I assumed for a pre-dinner drink. As I tried to get a cab, somewhere between the swampy weather and my heels stumbling down 2nd ave, I realized I was no longer sober.

Date

As I walked up the stairs to his place, I realized he was just locking up his apartment. No drinks, no chatting -- he just wanted us to head downtown together. I didn't blink, I didn't care, I didn't know what was normal! I was OK with what was going on. (Side note: I later learned that you NEVER go to the guy's apartment first, you meet AT the restaurant/bar/whatever spot so it's convenient for everyone.) We proceed with our date and head downtown to Supper.

Upon arrival, there was a few minutes waiting time, so we head to the bar for a glass of wine. By the time we sat down, I was drunk. This somewhat made up for the completely uninteresting conversation, which I barely remember, so I kept the drinks coming. My three leaves of lettuce did not soak up anything that was currently in my stomach, and it all kept spiraling downhill from there.

After dinner, I was back to my pre-date makeout drunken state. I of course thought I was slick willy, and convinced myself that he had no idea that I was three sheets to the wind. He suggested we go to Bar Coastal, a nearby bar. It was a dirty dive bar that was completely empty on a Friday night. As I offer to pay for a drink, he amusingly accepts. I don't know if it was because I was clueless or because I was so intoxicated, but whoever is asked out on the date should NOT pay!

What seemed like minutes later, Mark reaches under my dress with the simple thoughts of "easy access." I was floored! Who do you think you are?! We are in public! What is wrong with you!? He, on the other hand, saw nothing wrong with this. I had suggested going elsewhere for a little more privacy and he happily agreed. Looking back, I should have suggested a punch in the face. I was naive to say the least, and we went back to Mark's apartment.

It didn't take long for clothes to be ripped off. I was so incoherent, I had no idea what was going on. A few minutes later (it definitely didn't take very long) we were laying on his couch (yes his couch) and he says:

"I have to wake up really early."

These are words I've never heard before, but understood really well.

Me: "Are you fucking kidding me?!"

No, he wasn't. I pulled myself together, trying not to fall on my face, while he tells me he would love to see me again. I run out the door as quickly as possible, to meet up with other friends.

He, in fact did want to see me again and called me often. I decided to give him a second chance (I'm now fully aware of my completely dumb decisions, but this is how I learned each of my lessons) and with the second date of bad sex and Chinese food, that was the end of that.

He had continued to call me in the hopes of getting together again, but I never returned any of Mark's calls. I learned assholes don't get second dates, bad first-date conversations shouldn't lead to a second date, and to skip the pre-date bottle of wine.

Brooklyn..Need I Say More

While Lindsey* is at ComicCon dressing up as his favorite superhero, why stop the presses? If I have learned anything in my years of dating, as the cliche goes, it's to never put your eggs in one basket!

Meet Matt* This particular date verges into the realm of online dating. Despite what the rest of the world thinks, it is not easy to meet people in New York City. I'm not defending online dating, because let's be real, half these people are socially inept individuals that trick girls into thinking they are are tall dark and handsome while others are basically paying for sex via match.com, JDate, eHarmony--whatever their choice of poison may be.

Whether the exchanges between us started with a wink, a poke, a flirt-- we started chatting. His picture was super cute, dirty blonde Jew fro that appeared to be under control. He was all dressed up in a suit in his photo, possibly from a wedding (he's 34). We never really spoke of the unnecessary details of our own personal lives, but at the same time provided information that you would like to know about someone before going on a date. It wasn't weird, yet it was different.

Through our conversations we had both realized that we like the occasional "cool," yet not trendy bar and we both love dive bars. So the plan of action was to meet at the Blue Owl.

Date night: I waited outside of the Blue Owl, and for the first time in a while, I was excited. As I'm waiting, this tall "older" looking gentleman approaches me and he says hi! I looked at this guy like a deer in headlights. He was tall, just like he said, but he no longer had the Goldie Locks Jew fro. He had mousy brown short hair, a few "happy" wrinkles on his semi pimply skin. I wasn't convinced this was the guy I had been exchanging emails with for several weeks, but like an idiot and never actually confirming whether or not it was Matt, I followed him into the bar.

We sit down order a drink and for maybe the first 10 minutes, I was still convinced it was some other .com date that was confused. He then mentioned something that we had discussed, and I accepted that his picture might have been from his high school prom.

The conversation was worth the next couple rounds of drinks, so I agreed to let him blindly take me to another bar, which I was forewarned would be a dive bar. As we start walking to the next bar, I realize we were heading to the L train (non-New Yorkers, this means Brooklyn, which is pretty much my own personal form of hell.)

Me: "Are we going to Brooklyn?!"

Matt: Nods his head

We make our way over to the other borough, and he clearly doesn't seem to know where he is going. That's when the summer rain decides to set in. Umbrella-less, we have no idea where we are going, and in Brooklyn, most places close at about 10 p.m. We backtrack a few blocks, soaking wet and eventually make our way into the mysterious bar. He ordered a jack and coke and I got a PBR (when in Rome!) He then proceeds to drag me outside into the swampy NYC summer evening, and he shows me the mini golf course in the back of the bar. He was so proud that he found this awesome bar that there was definitely nothing like it anywhere else in the city. After a round of mini golf and some more drinks, it was midnight and I was a hostage in Brooklyn, I decided it was time to return to Manhattan.

We take the subway back (Brooklyn people don't believe in cabs), and with my dreadful thoughts of my 8:30am meeting, I tell him I'm going to get out at First Ave (the first Manhattan stop) and walk the 15 blocks (knowing the second I was out of the subway I'd hop in a cab and be home in 2.5 seconds.) Well, he wanted to be a gentleman and walk me home.

We walked the 15 blocks, continuing the slight awkward first date conversation. Finally we arrive at my apartment.

Matt: "I had a good time."

I provide him with hope and tell him I did too.

Matt: "Can I see you again?"

For my own sanity, I agreed to a second date, not really sure of what I actually wanted to do. Then, not really sure of the appropriate goodbye, he kisses me like some guy out of the 1950's; respectful, yet unsure what to do next. I bid him goodnight, and with that kiss I confirmed in my mind our second date.

If Everyone Went to Harvard...

Recent dating woe #1

Meet Lindsey*. In case you're wondering, he is not a she. I met Lindsey on the subway, one of those nasty swampy New York City days. We met up after his screenwriting class, I thought wow he's so versatile! He had suggested meeting in Union Square...in front of the Barnes & Nobles.

So there we were, in front of Barnes &Noble. "Where should we go?" said Lindsey. Um...I'm sorry did I miss the memo that said let's roam random areas of Manhattan. It's one thing, if you have been dating someone and you're walking around the city, but this is a first date for Pete's sake!

Anyway, we went to "The Coffee Shop." For those who are not from New York City, fyi: it is not in fact a coffee shop but a restaurant and/or boozy drunk stop at the end of an evening. We sit down at a table in the quiet area of the bar/restaurant and he orders tea. I'm not talking a long island iced tea, I mean a peppermint tea. As any proper lady (don't worry kids, I'm not following through with my mother's dreams of cotillion) I followed his lead and ordered a coffee.

Officially my first non-alcoholic date I have ever been on. There is nothing wrong with being sober sally, but as someone who thrives on drinking boys under a table, seeing me not drink is like watching a dog walk on its hind legs. Nevertheless, the conversation was pretty decent for a first date. (As we know, first dates are rarely "great.")

After about an hour and a half of him quizzing me on my life, I needed to know more about the doofy looking yet cute guy sitting across from me! He proceeds to tell me that he lived in some middle of nowhere town that might as well have had people walking around barefoot in overalls and couldn't wait to get as far away from there as possible. He continues...he went to Princeton undergrad and then went to Harvard.

How can you not respond with WOW!
ME: "What did you get a masters in?"
LINDSEY: "I was at Harvard getting my PH.D."

I officially felt like an idiot after telling him numerous drunken stories of staying out until 5 a.m. (including this past Saturday night) and wrestling another friend for her beer bong that she keeps in her apartment.

ME: "You're so humble about your education. You should wear it as a badge of honor!"
LINDSEY: "Most people become uncomfortable when speaking with such a smart individual."

Now, for anyone who knows me, it takes a lot to make me uncomfortable, which I of course informed him that, nope! still ok.

LINDSEY: "I sometimes make people uncomfortable with my smarts, and didn't have the "normal" college experience." (yea I got that part.) "With one beer, I'm tipsy and with two I'll black out."

Sadly enough, THAT was the comment that made me uncomfortable, a boy who can't drink.

After a trip to the restroom, Lindsey returns to the table, sits down and...

LINDSEY: "I think you're SO energetic. I am amazed by your energy in the best possible way and I have enjoyed hanging out! But I'm afraid that I will slow you down."
ME: "Uh...excuse me?"
LINDSEY: "I love your energy but I don't stay out till 5am drinking with my buddies and I don't want to hold you back by any means."
ME: "Uh...well, I have enjoyed your company the past few hours and..."
LINDSEY: "Okay great! We'll get together when I get back from my trip to San Diego!"

We walked to 23rd street where our paths went in opposite directions.

LINDSEY: "Do you want anything from San Diego?"
ME: "That's really sweet, but have a good time. Why are you going, by the way?"
LINDSEY: "I'm going with some friends to ComicCon." (For those of you who are googling what that is, it's a place for all dweebs and comic geeks alike to get together and have an excuse to dress as their favorite superhero (or villain) at the age of...38!

As my jaw drops to the sidewalk, I quickly give him a hug and tell him to have a safe trip.

I had agreed on a second date with him upon his return...he is really nice and yea, he's smart. Besides, I'm always looking for the nice guy instead of the asshole. Funny enough, I received a text from him this morning: "Hello from San Diego! And hello from me too!"

In thinking that "beggars can't be choosers," I'm sure he'll get a second date and a response to his text.

*Just to throw it out there, I will not be using anyone's real names because hey, some of the guys, despite what the critics (my friends) may think, sometimes you need to give them a second chance to realize how utterly awful they really are.

Dating Wars

At the age of 26, as a single New Yorker I would like to think that my life would consist of a steady job, a well furnished apartment that I call my own, great friends, and an amazing man to fill my life. Well, I've got all but the man. So what does that say about me. No, I'm not socially inept, no, I'm not some 700lb obese woman, I'm just me. A little rough around the edges (but then again what New Yorker isn't) looking for a man to fill the other side of my queen size bed, someone to share my life with, and of course someone to be my companion. I mean, I didn't think that was a lot to ask for, apparently...it is.

So, what you have here is not a bashing blog for how stupid men are or how my every wish is for a white picket fence in Connecticut with the perfect china pattern in my in kitchen (absolutely not.) I just think that every girl has been on the most absurd dates whether it be "the stalker," "the divorce," or even "that guy." We all know what it is like.