Home Advice & How-ToDating Single in New York? Make Her Laugh With These First Date Questions
Home Advice & How-ToDating Single in New York? Make Her Laugh With These First Date Questions

Single in New York? Make Her Laugh With These First Date Questions

by Nick Marshall

As a single man in New York City, it’s easy to become complacent.  Women outnumber men by quite a margin, meaning that on paper you shouldn’t have to stay single for long.  In practice, don’t bring anything less than your A-game.  Not only will you be going on some of the most expensive dates in the country, but you’ll also be dealing with highly-ambitious, financially-secure, no-nonsense ladies who won’t settle for an amateur.  Women in the city that never sleeps are easily bored, so make sure to sparkle from the start with these funny first date questions.  Their answers will also reveal everything you need to know about the true identity of your date. 

So, Who Were You Really Supposed To Meet Today?

New York City is notorious for its ghosting and flaking, particularly if you’re searching for someone on dating apps.  Everyone has been stood up or left alone at the bar.  Don’t take it personally if you’re ghosted, but do make a joke of it if you’re actually successful in your in-person meetup attempt.  It will serve as a great conversation starter as your date will likely have horror stories to share too. 

Want to put your date at ease?  Spokeo lets you show her that you have nothing to hide.  Enter your name in the search engine, and you have evidence that you’re not currently married, wanted by law enforcement, “borrowing” someone’s identity or a serial scammer (note: fees apply). In short, you’re a keeper. 

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How Far Would You Go on a First Date?

Before a glass of $7 New York City beer collides with your face, make it clear to your date that you’re talking about the subway system.  New York newcomers will explore all five boroughs, but experienced daters know the precise block and street where their romantic journey ends.  You need to know if you’re out of your date’s range, if not their league. 

If discussing the five boroughs has her brow furrowing, she may not be the city-dwelling New Yorker she chalked herself up to be.  Corroborate her city of residence with a simple reverse phone number search.

Which Movie Cliché Best Describes You?

Everyone is playing a part in NYC or following a dream that has been immortalized a hundred times on screen.  So which one best describes your date?  Are they a Holly Golightly escaping their past or rising up the ranks in a “Devil Wears Prada”-style corporate environment?  Pray that their chosen story has a happy ending and that said happy ending features you as the male lead.

If You Had $1 Million, Where Would You Rent a One-Bedroom Apartment? 

Actually, you’ll only need to find an average of $3,684 a month to rent a one-bedroom in the city, but the price of rent will rarely be off your mind or out of conversation.  Yes, even on dates.  Accept that price comparison and real estate are inevitable ice-breakers.  It’s the elephant in a very expensive room. 

How Would You Show Me You’re a New Yorker Without Telling Me You’re a New Yorker?

You don’t have to be born in the five boroughs to belong.  If you still can’t drive but can cross a busy street without breaking stride, navigate uptown without looking up from your phone and instinctively fold your pizza slice, you’ve made it.  Given that genuine New Yorkers enjoy a good argument too, your question opens up infinite possibilities to debate the merits of the Yankees or Mets, Brooklyn vs. the Bronx or why “Friends” is terrible/unmissable. 

What’s the Most Touristy Thing You’ve Done in NYC?

If your date can’t laugh at herself, you might end up as the object of her ridicule.  A constant source of mirth and scorn in the city is the tourist community.  Everybody who came from someplace else has a story to tell that reminds them they were once new here too.  Usually this will feature Times Square, Magnolia Bakery, the top of the Empire State Building or being burned by a fake taxi at JFK.  You can both laugh about it now, of course, knowing that after just a few months in New York, you learned how to spot a scammer from a block away. 

Would You Rather…New York Edition

The options are limitless.  Give up bagels or pizza for a year?  Go without heating in winter or air conditioning in summer?  Share your apartment with bedbugs or rats?  Lose your MetroCard for a week or your credit card?  If you’re looking to establish boundaries, there’s no better way to find out where your date draws the line. 

Here’s another one for you:  Would you rather date a woman who is dishonest about her criminal history or her relationship status?  Keep a people search tool in your back pocket (literally) to ensure you never have to settle for either (note: additional fees may apply).

Bear in mind that however slick your patter and however much your date is laughing, she may still ghost you.  This is New York dating after all, which is why it’s a good idea to do a little discreet background research on a new suitor if your gut is ever telling you that something is off.  Ensure your connection is genuine by validating important details like marital status, age, dating profile activity or even association to dating scams with Spokeo’s confidential name or reverse phone number searches.  Do your due diligence, ask the right questions and make her laugh on the first date, and you may well win a second.