A Typical First Date with a Guy in Boston, Chicago, or New York
How You Met
Boston: Attended the same biotech industry mixer.
Chicago: Saw each other’s reflection in the Bean during golden hour.
New York: Almost sat in the same pee puddle on the C train.
The Pickup Line
Boston: “I went to school just outside Boston. No, not Tufts.”
Chicago: “Call me Tom Skilling, because I’m forecasting some action later.”
New York: “I have an in-unit washer-dryer.”
Asking You Out
Boston: “Wanna get Italian food in the North End?”
Chicago: “We should grab a drink by the lake and pretend it’s the ocean.”
New York: “Let’s get condescended to by the staff at a West Village wine bar.”
What Time the Date Starts
Boston: “8 p.m.”
Chicago: “Tonight-ish.”
New York: “Whenever my first date of the night ends.”
Picking You Up
Boston: “Looks like the MBTA derailed again. We can split the forty-seven-dollar Uber.”
Chicago: “I’ll take the 22 bus to the red line and transfer to the brown line, then walk fifteen minutes to your apartment. I may have grown a full beard by the time I reach you, but it’s me.”
New York: “You can hop in my Citi Bike basket, but you’ll have to be my eyes.”
What Drink He Orders
Boston: Whatever Sam Adams is in season.
Chicago: Malört and a lecture on the history of Malört.
New York: A “Manhattan” (any drink that’s viral on TikTok and twenty-five dollars).
Food Complaints
Boston: “My mum makes a way better chicken parm than this.”
Chicago: “I cannot stress enough how mad I’ll be if there is ketchup on this hot dog.”
New York: “They called this a glaze, but it’s obviously a reduction.”
The Sports Small Talk
Boston: “The Sox sucked this year.”
Chicago: “The Sox sucked this year.”
New York: “At least the Sox sucked this year!”
The Pet Discussion
Boston: “My childhood dog, Brady, passed away last year. It’s okay, though. He was really old.”
Chicago: “My cat’s name is Ditka, and he can only fall asleep to episodes of The Bear.”
New York: “She’s a Pomapoo named Chelsea, and she’s terrified of grass.”
The Family Gossip
Boston: “My Nana, rest her soul, knew one of the guys who robbed the Isabella Stewart Gardner Museum. She refused to say where the art is buried.”
Chicago: “My cousin in Naperville tells people he lives in Chicago.”
New York: “My parents are Democrats, but they’re Eric Adams–Andrew Cuomo Democrats.”
How He Asks for a Second Date
Boston: “Up for Wahlburgers next Saturday? Let’s go to that one across from Dunkin’. No, the other one across from the other Dunkin’. ”
Chicago: “Wanna come to my friend’s Second City improv class graduation show? It’s this Wednesday at 3 p.m.”
New York: “There was a rat in my salad, so we can come back here for free next week if you’re down.”
