First date ideas for NYC’s online daters

The whole “dinner and drinks” thing gets old pretty quick.

Whether you’re looking for a relationship or just a little fun, first dates can be a little awkward. Tinder and other online dating services help take some of the sting off the awkward, but a solid date idea helps a lot more.

The whole “dinner and drinks” thing gets old pretty quick. It also puts a nice little dent in the ol’ wallet.

I’ve decided to put together a list of first date ideas. Now there are a ton of lists on the Internet about date ideas in NYC, so I did my best to make mine a little different.

Serious daters and those looking for a quickie can pick from the list.

Happy hunting.


People Watching


New York City is known for a lot of the best sightseeing on the planet — skyscrapers, parks, you name it. But the best sightseeing NYC has to offer is people watching.

People watching is good for a first date because it takes some of the focus off of the actual date and puts it on whoever happens to be in the area.

Every NYC dating list has some variation of parks and picnics and blah, blah, blah. Pick an outdoor spot like Central Park or the High Line (these are the two best people watching locations in NYC), bring food and booze if that’s your thing (just keep it concealed), sit back and let the people watching begin. 

I like to give the people I’m watching a little backstory, but that’s just me. Going along with the “backstory” theme …


Role Playing


I don’t mean sex role playing, although that’s fine, too.

This idea takes meeting for drinks to a different level and helps avoid the same boring banter you deal with on a first date. Pick a place to meet, preferably a bar where you can sit down and hear each other.

You’re both responsible for coming up with your own background stories. Make up literally whatever you want — names, job, hobbies — and put some effort into it.

If you’ve ever watched “Modern Family,” I’ve got two words for you: Clive Bixby.

This is probably more for those of you looking for quick hookups. Regardless, have some fun with it.

If it were me, I’d be Bulk Hogan, porn star. I won the 2012 Adult Video News award for best male performer but I’m looking to leave the industry.

Trust me, there’s a whole background story ready to go.


Museum of Sex (5th Avenue at 27th Street)


I’m embarrassed to admit this, but I’ve never been, although I should probably have my own exhibit at this point.

For those of you who are unfamiliar, the Museum of Sex, like any good museum, teaches. But in this museum, you learn about the history of sexual activity.

This is good for a first date because it forces you to discuss a subject some people other than myself have a tough time talking about — sex, if you couldn’t figure it out.

The museum’s website also advertises a bouncy house with inflatable boobs, so apparently there is a God and he’s been taking requests from me like it’s TRL circa 1998.


Boozy Brunch


Drinking helps numb the awkwardness of a first date.

Day drinking — especially anywhere that has outdoor seating now that it’s nice again — is even better.

If you’re not a drinker, that’s great. But to quote my favorite comedian Jim Jefferies, “I love drinking. Hate people who don’t drink. I’ve never met an interesting person in my life who didn’t drink.” I live by that.

So find a place that does unlimited drinks for brunch and cut loose. By the second half of the brunch, the conversation should be flowing.

If you’ve done brunch right, then you’ll both want to stop and jump in the inflatable boob bouncy house when all is said and done.

Head to every Friday for Matthew’s latest column. To inquire about NYC dating advice, email him at Your question may appear in a future column, but no names will be used.