Brittany Simon’s date showed up with some surprise shortcomings. Dressed sloppily and standing 3 inches shorter than his self-proclaimed height, the investment banker barely resembled the Facetuned photos he had posted on the League dating app. Still, Simon was willing to overlook all that — until the guy started grilling her about her paycheck.
“He was like, ‘How much money do you make a year as a personal assistant?’ ” the 24-year-old Soho resident tells The Post of the April encounter. “I was very taken back.”
Nosy first-date questions have become a New York nuisance rooted in the city’s culture of directness and ambition, says dating expert Devyn Simone, a matchmaker at Three Day Rule. “New Yorkers are focused. They have a checklist of what they want in a date. They’re more upfront than ever with their questions,” she says. As a result, a romantic dinner can feel more like a grueling job interview … for a position you might not even want.
‘A romantic dinner can feel more like a grueling job interview … for a position you might not even want.’
To deflect her date’s prying, Simon tersely said she earns more than enough to be self-sufficient. Then she excused herself to the ladies’ room — and returned to cut the date short with news of a fake roommate emergency.
Simon, who recently moved back to New York by way of Los Angeles, says she’s routinely startled by first-date interrogations about everything from her educational pedigree to how much her apartment costs. “I would never be asked these things in LA,” Simon says. “New York is a concrete jungle of money. Guys feel entitled to know that you’re financially stable and not a gold digger.”
A desire for immediate gratification could be driving the bothersome background questions, Simone adds. “There’s this mind-set that we don’t have to be patient in New York,” she says. “We can get underwear, ice cream and Plan B delivered to our door in a matter of minutes. Being direct on a first date may be someone’s way of saying ‘I don’t have time to waste.’”
Hypothetical questions can be pushy, too. Lindsay Dreyer, 33, was enjoying a fun first date with a handsome, accomplished suitor in 2013 when the subject of family values came up.
According to Dreyer, head of content and communications at online job marketplace Werk, her date asked, “What would you do if we had a baby, and the baby were gay?”
To which she responded, “Other than love the child unconditionally?”
He in turn said he “would struggle” with the situation, and an awkward conversation followed. After going back and forth about their moral values and political views, Dreyer had heard (and said) too much. The two haven’t seen each other since.
In today’s intense political climate, Simone says hot-button questions are tough to avoid. But they don’t have to be a deal-breaker — provided your date doesn’t dismiss your beliefs.
“Exploring differences can create an opportunity for thoughtful discussion and actually bring two people together,” Simone says. Her advice: Don’t get defensive. “If there’s an issue you feel strongly about, go ahead and share your opinion,” she says. “Then give your date the chance to share his, and try to understand where he’s coming from.” If your date doesn’t grant you the same respect, simply make a mental note that the person isn’t right for you. Says Simone, “No sense in flexing on your point unless you want to get into an all-out political brawl.”
For Ryan, a 28-year-old engineer based in Bed-Stuy, a presumptive and overly personal question confirmed he’d never last with a woman he met on Coffee Meets Bagel.
Halfway through their 2015 dinner date, the woman asked what he wanted to name their future children. That was the moment Ryan realized that he’s not looking to start a family — with his date or anyone else. “It occurred to me at that point that I don’t want kids,” he says.
He also didn’t like the name she chose for their make-believe baby.
“It was something like Aiden or Jaiden or Raiden — some supermillennial name I couldn’t stand,” Ryan, who didn’t want to disclose his last name for professional reasons, tells The Post. There was no second date.
Simone says broad questions about relationship goals are to be expected on a first meeting. For instance, it’s not impolite for a date to ask whether you’re looking for a long-term partner or dating casually right now. But don’t feel pressured to answer questions about a distant future scenario that assumes you two will be together. In that case, Simone advises dialing back the conversation to more general terms. Try something like, “It all depends on the person I end up with” or “Ha, I wish I knew the answer. Wouldn’t it be great if everyone could see their future?”
A gracious approach is what worked for Alex, a 22-year-old publicist who met his current boyfriend on an awkward 2015 date that included a string of questions about his most recent ex.
“The topic is very personal — and not really an attractive point of conversation,” says Alex, who lives in Maplewood, NJ and also asked that his last name not be published. So Alex kept his response simple and positive: He told his date that he had been in a relationship that wasn’t working and that he was hoping to move forward from the experience.
“It’s a technique that lets you get away from the topic of your exes and start building a foundation with someone new,” Simone says.
Alex did just that, and he’s been with his boyfriend ever since.