Choose Your Own NYC Dating Adventure

  1. A Set Up with a Friend of a Friend
  2. A Hinge Date
  3. A Craigslist Missed Connection
  4. Your Cat

The Attire:

  1. It’s a Tuesday night and you had to work late. You’re in the outfit you had on at the office, which is more corporate than casual, and you’re slightly bummed you didn’t bring better shoes to change into.
  2. It’s a torrential downpour. You decide to forgo the wellies and rain gear and sport your new American Two Shot sneakers in hopes of looking groovy, but you arrive soaking wet and you have to deal with wet shoes all evening.
  3. The same outfit that you wore on the subway when you first encountered your date. How else will they recognize you?
  4. You have chosen to wear an oversized nightshirt that you think your date will love. It reads: “The Cat’s Pajamas.”

The Spot:

  1. You get a text to meet them at UCB to watch their friends improv 101 final performance. You roll your eyes knowing it will not be funny, but you will need to force pity laughs to ensure an okay date.
  2. You’re meeting them at Bia on South 6th because it’s the midway point between your apartments.
  3. You’ve never been on a sober date, but since you met through Craigslist you find that it may be the best choice. A Saturday morning (12 noon) at Peck’s because you’re convenient neighbors in Clinton Hill.
  4. You go back and forth between the couch and the bed because your roommate is so damn skittish.

Your Date:

  1. Not sure why Jeremy set you guys up—your date is attractive, but seems like they work in finance and may have never taken the subway. At least you’ll get a free Uber out of this.
  2. Your date is first to arrive, dressed in complete rain gear, and you feel like the loser trying hard by not sporting appropriate weather attire.
  3. You know you have an instant attraction, but the conversation is awkward and you’re both hungover from the night before.
  4. You and kitty have had date nights before, but this particular night your date scratches you a number of times and has “had it with you!”

The Drink:

  1. You grab beers at the comedy counter for you and your date. Naturally, you wished you had something stronger.
  2. You have to work tomorrow so you planned on just having a few beers, but your date is thinking otherwise and orders you each shots and a mixed drink…and that’s just the beginning…
  3. You ordered a “flat white” thinking that would impress your date. Unfortunately, it doesn’t sit right in your hungover belly.
  4. Milk for kitty and a few of your roommate’s Modelos from the fridge (He won’t notice).

The Departure:

  1. After the less than mediocre show, your date went in for a kiss and you turned your head. You will get four texts over the next week that you will choose not to respond to.
  2. You wake up from an alarm in a strange apartment in Bed Stuy. Your date is beside you and you, but doesn’t stir. You’re late for work and beat feet as quickly as you can!
  3. You exchange a quick hug, but plan on meeting the next night for “adult beverages” this time.
  4. What departure? You wake up and your date is sitting on your chest and pawing at you; at least they only way 11 pounds. Thought Catalog Logo Mark


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