73. May - July 2012: Emmett, a.ka. Airport Guy

What's that saying about taking lemons and making lemonade? How about taking a five hour flight delay and getting a date out of it?

How did you meet? O'Hare airport

Name: Emmett

Height: 6'2

Age: 27

Occupation: finance

Good quotes from date:

Him: "I'm feeling really loose."  (after 3 drinks. He doesn't drink that often)

Him: "I'm so exhausted!"

Me: "Why? It's July 4th, you had off from work. Why are you so tired?"

Him: "I had a really hard-core work out at the gym today."

Me (in my head): There is no response in this world that can bore me more than this one. File away for blog post.

Why is he still single? Although sweet, he's self-absorbed and immatureHe doesn't know how to navigate the dating world: longest relationship ever = 2 months.

Did he pay for the date?

We split everything and he said how refreshing it was to date a professional woman who can pay her way. I refrained from telling him how un-refreshing it was that a professional dude can't pony up and buy a professional woman a drink.

Did he contact you after the date? Yes, via text and phone call

How many dates did you go on? 2 dates and 1 group date

Would you recommend to a friend? no


After the Delta shuttle screwed me again and cancelled my flight home due to thunderstorms (and didn't announce it at our gate, I received a text message from Delta), the guy sitting behind me and I started to complain and discuss which flight to get on next. He was in town for a bachelor party and was hungover. I was tired, dressed in a typical plane outfit (think loose everything), and had no make-up on. Five hours and many unhealthy airport snacks later, he found me at our new flight's gate and chatted me up. Got my number and 2 weeks later we went out.

Date 1:

On a rainy evening he came all the way to my neighborhood. He got a little drunk and silly. I noticed he is really tall and handsome and an excellent dresser. I like this. We shared a little smooch on the sidewalk at the end of the date. I still like this.

Date 2:

This time I went to his neighborhood and he took me to one of his favorite restaurants. I offered to split bill (like I did last time) and he accepted - again. He held my hand, cuddled with me on a bench in a park and we kissed some more. He talked about himself most of the time, the majority of which included him whining about how he didn't want to play in a soccer game later that night, but really he has to, but he doesn't want to, but if he doesn't show his team won't win, because, yeah, he's that good. I like this less and less.

Date 3 - group date

Several weeks later it's July 4th (he was out of town for 3 weeks). He called me when he got back. I needed to see him one more time to decide if there was anything between us besides my physical attraction to him. I invited him to meet my friends and I at a bar and to watch fireworks on a rooftop. The owners of the rooftop are a couple who I just met that very same night.

Aside from flirting with my blond friend the entire night and not paying for the pizza we ate, he won the prize for "most annoying date in the world". He whined about how much he wanted to see the fireworks, and guys, what if we miss them because we're eating pizza? They start at 9:20pm we better get up there....yadda, yadda, I tuned out.

Let me reiterate: we were at a friend of a  friends' home who kindly gave us booze and an invite to their rooftop. Any mature person would shut the hell up and let the hosts guide us upstairs when they are good and ready. I worried I might shove him off the roof by accident.

Once on the rooftop he whined about how the fireworks should just hurry up and end so he could go home and sleep because his day at the gym was so very tiring.


Sorry folks. I'm an adult now and no matter how hot you look in a pink buttondown shirt, I can't  keep you around if you are annoying as shit. Two days later he left me a "happy birthday" voicemail. I decided to phase him out and not respond. One week after that I got a text message asking if we can just be friends to "expand our networks" and that I should think about it. I've thought about it.

No thank you. 

69. April 2012: Jay, the Kiwi

How did you meet? Offline! At a concert, we started chatting at the bar. He asked for my number after the show. He texted that night.

Name: Jay

Height: 6'3"


Occupation: film editor (this might be the 57th film editor I've dated)

Good quotes from date:
Via text: "What was I thinking? I'll never let you walk home alone again."

Why is he still single?  Because of his age?

Did he contact you after the date? No. See comments.

How many dates did you go on? 1.5

Would you recommend to a friend?
No. I still have a crush on him.


Jay and I had a very promising start. We met in person, we chatted, we obliviously found each other attractive enough to want to see each other again. He was super cute and his New Zealand accent didn't hurt his sex appeal. 

The first time we hung out was a few days after the concert. He was at a bar with friends in my neighborhood so I stopped by. Not an official date, but we spent the whole night talking to each other and we shared a lovely late evening make out. He offered to walk me home, but it was out of his way so I objected. I woke up the next morning to the text above with butterflies in my stomach because I was smitten. He was a gentleman AND I felt attracted to him - A rare combination indeed.

Jay followed up immediately after that night and asked me out on a real date - to see a movie by a New Zealand director. Thoughtful, no? The movie was adorable and so was my date. He bought the tickets, the popcorn, the soda. We got drinks afterwards, I bought him one drink and he refused to allow me to buy anything else. He was very inquisitive about my life and experiences and seemed genuinely interested in my answers. 

We left the bar at 1am on a Thursday night and when I said I was taking a cab home he offered to share one and said he'd pay. (We don't live in the same neighborhoods in Brooklyn so this was not a cost effective choice). Again, I was flattered. 

In the cab my drunken self had to fight the strong desire to jump his bones. I wanted him to make the first move like he did last time. He did not. Even my drunken self had a hunch that this was not a good sign. A quick kiss on the lips as I exited the cab and a "See you soon." The kiss of death literally and figuratively.

Four days later I asked him to join me for a comedy show, which we talked about seeing on our date. NO RESPONSE. 

If I had a dollar for every boy that ignored my text messages this blog would be feature-length film and I'd be living off the royalties on a Caribbean island. Why is it so easy to ignore a text? Why is it so easy for my feelings to be hurt (albeit briefly) by a guy who ignores my text? I'll never know.

I'll also never know what happened with Jay...but my minimal analysis is this - our age difference. I don't know how old he was, I only knew he was younger because of his school and work history. I'm guessing it was about 8 years difference. Maybe that scared him off? Or maybe this is just an excuse I tell myself to feel better. 

However, I do know this - I'm proud of my age and my life experiences and I wouldn't change that for anything.