The First Date

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The First Date

Brie. A Boombox. A Boston Terrier.

Who’d have thought that these three things could come together to make the best first date I’ve ever had in NYC*?!

I had been in New York for less than 2 months when I met Scott** at a friend’s birthday. He was so charismatic, outgoing, and fun, and I was instantly attracted to his energy (and, of course, the fact that he was a ginger***!). He knew I loved dogs and being outside any chance I could get, so he planned a first date for us on a sunny afternoon in Central Park, telling me to bring my pup Feeny (named after one of the greatest TGIF sitcom stars of all time!). As Feeny and I walked over to meet him, I was surprised to see he had an adorable black and white Boston Terrier with him.

“Who is this?” I asked, knowing Scott didn’t have any pets.

“I ‘rented’ him for the day from a friend of mine,” he told me. “Not too soon for a double-date, I hope?”

When we got to the park, Scott had picked out an awesome spot to set up a surprise picnic, complete with an old school wicker basket and gingham blanket. I was psyched to dig into the meat and cheese plate he had laid out. (Sorry, Nana – not kosher!)  

“I remember you mentioning that you’re a no-carber, right?” he asked, spreading some brie on an apple slice for me. (Technically, an apple is a carb, but #YOLO, baby!) To top it all off, he then whipped out a little boombox and put on some Frank Sinatra. It was a pretty awesome afternoon. Plus, the (unneutered) Boston Terrier was totally into Feeny. (Too bad Feeny didn’t have the balls – literally – to reciprocate.)

Now, 7 years later, I still remember this date as one of my most memorable. It was creative and not costly (though I don’t know the going “dog rental” rates!), thoughtful, and fun, and it provided us with a chance to actually get to know each other, too. While we did go out again, Scott soon moved abroad for several months, and I met my first NYC ex-boyfriend in the meantime. In any case, wherever Scott is now… HOLLA!  (I think I saw him on a Citibike recently, actually – wear a helmet, mister!!)

Dates have become less and less magical these days, especially when so many peeps are out meeting strangers from online and apps. Why plan to spend time and money on someone you’ve never met in person, especially given the probability that you’ll realize in the first few minutes that there isn’t any chemistry? I do think, if you’re meeting someone you’ve never met before, whether through a set-up or online, a simple one-hour first date of a drink or coffee is a great, no-pressure way to see if there’s enough of a connection to get together again. A second or third date is the perfect time to think of something more thoughtful or creative, or even just to look into a cool new spot neither of you have tried. Whatever you do, make sure you have a reservation, or pick a place that won’t have a long wait. (I waited THREE hangry hours standing against the crowded bar at Ippudo waiting to be seated on a first date once.) A place that’s not too crowded nor too loud is also key. And, guys, whatever you do, know that girls plan what to wear ahead of time, so don’t “surprise” her with tix to a Yankees game when she was under the impression y’all were heading to a swanky cocktail bar! While the idea itself might be awesome, the execution is definitely important. Oh, and everyone: please put your phone away, will ya?! In the end, if you’re meant to hit it off, you will, but a really great date can only make the experience that much more conducive and fun! 

Check out this list below of great date spots. In addition to some amazing suggestions y’all submitted, I’ve included recs from my own personal experiences, hyper-linking them to reviews I’ve written, too! Have fun!

Great Cocktail/Coffee Spots

  1. The Winnie (ask Mario for his special cinnamon orange shot!)
  2. PDT
  3. Shalel Lounge
  4. Little Branch
  5. Maysville (attn: whisky lovers!)
  6. Kobrick Coffee (coffee AND cocktails speakasy spot)
  7. Ace Hotel (great Stumptown coffee and cocktails on comfy couches)


  1. Queens Archery
  2. The Royal Palms Shuffleboard Club
  3. Pioneers
  4. The Uncommons
  5. Barcade
  6. Dave & Buster’s (so silly, but so fun!)


  1. The MET Rooftop (not many people know about it!)
  2. Rooftop Cinema Club
  3. Mini golf at Chelsea Piers
  4. Ice skating at Rockefeller Center or Central Park
  5. Rooftop pizza and wine at Fornino in Brooklyn Bridge Park
  6. Conservatory gardens in Central Park


  1. W 8th St.: an awesome street for dinner, drinks (Happy Hour at Amelie = 3 glasses of wine for $12!), bubble tea, frozen yogurt, foot rubs, army surplus and Western wear shopping.
  2. Brian Newman Show at Django at The Roxy TriBeCa (jazz/burlesque – see right! And look closely…)
  3. Raaka Chocolate Factory
  4. Sushi Roxx
  5. Van Brunt Whisky Distillery
  6. Ride the new Astoria ferry and check out a great Greek restaurant in Queens
  7. Bird Land Jazz Club
  8. The Frick (followed by drinks at the boathouse)
  9. Open House NY (one weekend per year)

I couldn’t post all of these great date ideas without sharing the worst date I’ve ever had with an ex-BF – check it out here!

* While not in NYC, I have to give credit where it’s due to my very best first date Andrew, who, after meeting me in Vegas, met up with me in L.A. to treat me to the greatest steak ever at a beautiful restaurant overlooking the beach, then played carnie games with me at the Santa Monica Pier before topping off the night on the ferris wheel right in time to see July 4th fireworks. Best first date EVER!!!

** Names have NOT been changed to give credit where it’s due, y’all!

*** Others that share my fetish for the fair and freckled: Think twice about seeing the movie IT that I saw last night – Pennywise is a total ginger buzzkill.

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