100. Oct 2014: David, Mr. Whiskey - The Date to End All Dates

How did you meet? Oh, this little Instagram video contest, #BeMy100 I launched. His video was creative, he was cute, confident, and I laughed every time I watched it. (And got the most likes).

Name: David (his real name!)

Height: 5' 10"

Age: 35

Occupation: finance stuff

Good quotes from date(s):

Him: "Do you have a fear of abandonment?"

Me: "By my friends and family? No. By men, probably. Yes." 

Him: "Do you think we'll kiss?"

Me: "Yeah"

Why is he still single? Has trouble being vulnerable

Did he pay for the date? Yes

Did he contact you after the date? Yes...you were all there too, see our People Now appearance

How many dates did you go on? 1 (really like 3 dates in one)

Would you recommend to a friend? Yes


This date had no chance to be a typical date. I created a public contest to find a date, then picked him on live on People magazine's show, People Now. David was fully aware of this blog and that I’d write about him. 

On top of all of that I was fully out. No longer an anonymous dating blogger, the world became fully aware that I am me - a woman with a face and a real name. So naturally this was unlike any other. 

Basically, this date, #100, had to kick my other dates' asses. Luckily, it did. 

Partly because of David, who was open to anything (I mean he had the balls to enter this contest and agree to go on a show to talk about it), and partly because - like any good romantic comedy - New York City played a starring role in the evening. The city after all, is my longest lasting relationship to date (12 years).

Our 10 hour date began with ice skating, ended at the top of the Empire State Building, with a long delicious dinner in between. Here's what happened: 

I headed into Manhattan [vine video] with a backpack for my post-activity wardrobe change and nervous butterflies in my stomach.

On a bench outside Central Park I pretended to be busy on my phone when David arrived with a pink rose. I felt like I was in an episode of the Bachelor. It felt lovely. (The last and only other time a date brought me roses on a date, by date 3 he turned psycho.

As we walked through the park to the ice skating rink (David carried my backpack - chivalry not dead!), I imagined us reenacting “When Harry Met Sally” with me asking David if he thought women and men could ever really be friends. Instead, we noticed a Big Bird sitting on a bench taking a rest (maybe stoned?) with Cookie Monster on his lap. For a mere $5 we got a picture and we broke the ice. 

Unknowingly I coordinated my scarf with Sesame Street.

Unknowingly I coordinated my scarf with Sesame Street.

Meanwhile on the real ice, the breeze was unseasonably warm and I skated slowly, hoping David would catch me if I stumbled (he's played hockey his entire life). We circled the rink, surrounded by kids, high rise buildings, and leafy trees and got to know each other. We asked each other questions, we listened, we laughed. We both fell once, he first, due to a "toe pick" situation, and I realized we were reliving the movie Cutting Edge, minus me being a graceful figure skater.

Date selfie

Date selfie

We managed to make a Vine video and not kill ourselves. Like the classy gal that I am, after turning in our skates I changed into my dinner dress and boots, and slapped on some mascara in the rink bathroom.

My first bathroom selfie. No, it will not ever appear on my Tinder profile. 

My first bathroom selfie. No, it will not ever appear on my Tinder profile. 

Cocktails and shareable plates at Beauty and Essex got us drunk and full. Over our three hour dinner we chatted about everything. David was easy to talk to.

I enjoyed living in the present not thinking about what would happen next, which is one the most important lessons I’ve learned from this project. Those are the moments when I am the happiest.

Yet I struggled to maintain the “zen” dating philosophy because David and I had a social media mission to accomplish. During dinner he caught me tweeting while he was talking, and suddenly, embarrassingly I realized I'd became my own dating "DON'T". Put your phone away, people. Seriously. There’s a time and place for Instagram and Twitter. And it’s not dinner.

...Wait until dessert.

A 3-hour dinner should end in 3 desserts.

A 3-hour dinner should end in 3 desserts.

High on sugar and wine I wondered if we would kiss. He read my mind and asked me if I thought we would. Sure, I said. I’m the girl that likes make outs (see all previous posts and this video). We stumbled into a cab uptown to the Empire State Building. 

I haven't been to the top since I was a kid and I have never been at night. We walked around the observatory deck because I needed to see my city light up from every angle. Yes, yes I did smile thinking about the ending to Sleepless in Seattle.

NYC, like my third parent, welcomed me with open arms at 23 yrs old one month after September 11th, 2001. From the Upper East 80's to the Upper West Side, to Greenpoint, Brooklyn, she has seen me grow up, fall in love, break up, breakdown - she's witnessed all of my adulthood so far. I was glad to spend my 100th date with her too. 

How to end a date that began with a video and a shot of whisky? With a shot of whisky. 

The original shot glasses from David's Instagram video.

The original shot glasses from David's Instagram video.

After that, David and I hugged and went our separate ways. This wasn't the date to end all dates, rather it was the best date to end this project. It was truly special. Thank you, David, for being a part of it.

At the end of the night it was still me by myself. Alone but not lonely. 

As I stood at the counter of my neighborhood 24-hr bodega waiting for a turkey sandwich that I knew I'd eat in bed while watching Netflix, I felt the end of something (not my drunken late night habits, apparently). It was the close to an important chapter of my life that I opened 4 years ago never knowing what it might become - who I might become.  

This end is also the beginning of something else. I’m single, so I will continue to look for love and unless someone invents some other method of meeting people, I will date. I will continue to write because it is who I am now. I hope you continue to read because you all are a part of me too.

What’s next? A book? A play? A screenplay? A web series? Maybe, yes.

Truthfully, I don't know and that excites the hell out of me.