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.



You're Cordially Invited to My 100th Date Tonight

I've been on my 99 first dates so you've heard. The first few I was definitely nervous - what to wear? What to say? How to greet him? How to make him laugh? General worries about how not to be a total ass. 

Eventually I got the hang of it, like anything you practice doing over and over. Today is my 100th first date and I'm crazy nervous! 

For more than a month I've talking about this date, and for more than a week I've been talking about who this date will be with. We know what we're going to do, but what happens during the date is a complete mystery. 

It all begins when I meet David at the Southeast corner of Central Park at 5pm (NYC time) today. 


I should not be typing this. I've had too much caffeine. I'm running late for brunch with my best friend followed by a blow out so my hair doesn't do weird things tonight. My nails are painted "Jiggle Hi, Jiggle Low" by Essie, which is totally appropriate for the evening to come. 

photo (9).JPG

I'll soon pack a date bag. That's right, I'm going to Manhattan, and a date that goes from day activity to nighttime fancy dinner needs two outfits.

(Do I sound cool and casual about this? If so, I'm LYING. I'm a girl who normally gets ready in under 30 minutes because my dates are usually in Brooklyn at dive bars where the guy I meet is too cheap to buy me a my beer).

For dinner I'll put on this dress I bought in Copenhagen and wore for my birthday party in July. I felt sexy then so it gets the job done. There's also a little opening in the back, just sayin' David. And of course, my go to black booties, Wolverine 1000 Mile by Samantha Pleet. 


And because PEOPLE Now has given us a social media mission to complete, I'll be sharing pics and videos and tweeting throughout the night. Finally you all can come on a date with me! Follow the hashtag #bemy100


Well, I can't predict the future. If I could, I'd be a gazillionaire who wouldn't have gone on 100 first dates to find her life partner. I would be able to meet someone new, flash forward to our bad date and reject him on the spot. THINK OF ALL THE TIME I'D SAVE!

With that time I'd busy myself with adventures like traveling the world, writing novels and hilarious screenplays, and finding cures for incurable diseases, all of which would lead to several nobel prizes, and I'd be...I'd be...probably...bored.

The thing is, I like life because more often than not it surprises the hell out of me.  

I hope I'm surprised on my date with David. I hope we laugh, smile, get to know each other, eat and drink, and maybe feel a little magic. See you on my date!

In the meantime...before date #100 have a look back at date #1 from 2010. I wrote: "For my first foray into the world of online dating this year, it wasn't so bad."

We've come a long way baby.