This One’s for the Lovers: Dating in the City that Never Sleeps

Well friend, I told you I would be back. It is a warm, rather stormy day here in the city. For the past few weeks, we have been suffering the effects of a heatwave and lemme tell ya, New Yorkers are not having it. The other day, I even found myself feeling a bit overwhelmed by it. I (an idiot) thought it’d be a good idea to walk from the East Village to the Upper West Side in 95 F degree weather. I’m sure, by way of deduction, you can assume that it was in fact not a good idea. However, I managed. My reward for trekking 8 miles in this ridiculous heat? A lovely dinner at an iconic burger joint in the West Village. Oh, and a spontaneous stop by Levain Bakery! I have this thing where once a year, typically in the summer, I’ll treat myself to half a cookie at Levain. I either freeze the other half for a rainy day or, more likely, I’ll give it to a friend/boyfriend. It’s a simple tradition, but one I look forward to each year.

Speaking of cookies and boyfriends, I’d recommend a trip to Levain Bakery (the original W 74th location) as a date idea for any couples who are looking to keep the romance alive in the city that never sleeps. However, I suggest going in the early autumn – when the trees are beginning to swap out their vibrant wardrobe for a warmer toned palette. Cozy up to your lover on a bench in nearby Central Park and enjoy the warm, gooey cookie together.

I’m sure you’ve watched a movie or television show depicting women and men navigating romance in New York City. Whether it was watching Carrie Bradshaw at her laptop, trying to make sense of a complicated relationship involving a certain dark-haired finance man or witnessing Meg Ryan pace the autumnal lanes of Central Park alongside Billy Crystal (heart eyes forever!), we’ve all (secretly or not so secretly) wished we could fall in love in New York City. I certainly have. And I am here to tell you that it is both the worst and the best.

Dating in the city is like traveling abroad solo. It is uncomfortable and sometimes unfamiliar. While exciting, it’s mostly awkward. You’re trying to communicate where you’re wanting to go, but you’re not sure the other person understands. Sometimes you’ll land in a town or city or scape of sorts that speaks to you. It is the reason you went on this silly journey in the first place. You begin to fall in love. Whatever unpleasantness you once felt takes flight and in flutters this consuming sense of ‘I could make a home here.”

I’ve been on my fair share of dates here. At most, they either provided an entertaining story or cool bars and museums I’d want to hit up another time. I also learned that if you’re living in Manhattan and are trying to date someone who lives in Brooklyn (or vice versa), this sort of relationship/situationship might be considered long distance. It sounds snooty, but it’s a real thing. I have a hard enough time trekking to BK just to see my friends. Committing to an inter-borough relationship is a task not for the faint of heart. I own up to the fact that I just didn’t have it in me. When you live and work in one borough, you don’t really have an abundance of time or energy to dedicate to other boroughs. At least, not on a daily or regular basis. If I’ve learned anything about New Yorkers, it’s that we get comfortable in our neighborhoods. And by comfortable, I mean it can be inconvenient to leave.

But this does not mean your date nights should revolve around your neighborhood. While I consider myself more of a “homebody”, I do enjoy exploring other neighborhoods with my beloved. Earlier this year, he and I decided that we’d try out a new bar or restaurant every week. And so far, it’s gone swimmingly. We’ve been able to venture out of his neighborhood and over into the eclectic East Village, funky Williamsburg (Brooklyn is the new Manhattan I’ve heard!), fashionable SoHo, trendy Tribeca, and yes – even Midtown. On these date nights/days, we’ve been able to experience the most incredible food and drink the city has to offer. Not only that, but this setup has allowed us time to reserve for each other in an otherwise suffocatingly busy week.

Dates don’t have to involve dinner or drinks either. Thankfully, the city offers a plethora of fun & creative date ideas such as taking in a Broadway or off-Broadway show*, going for a leisure stroll through her many parks*, laughing together in a comedy club, biking from one borough to another, hitting up one of the hundreds of museums that sprinkle the neighborhoods, getting cozy at an underground jazz club, engaging your inner child by swinging on Pier 35 while inhaling the sparkling cityscape. You and your date could take a cooking class or a mixology class, you could head over to the West Side Highway for a round of tennis or the ever-so popular pickleball. If none of these activities sound interesting to you, then try out the Central Park Zoo or the more expansive Bronx Zoo.

Whatever the season, whatever the weather – there are countless ways to enjoy the city with your date. That’s what’s great about New York. She’s always got something for you to do. Whether it’s dinner and drinks, a game at CitiField, or a rainy day spent at the MET – there’s nothing like it anywhere else.

Like I said, dating in New York is both the worst and the very, very best.

Now it is time for this author to sign off, though I assure you that I’ll be back quite soon.

Au revoir!

* Might I suggest going to see: Some Like It Hot, Moulin Rouge, The Lion King, Wicked, & Six. Afterwards, try going for a kiss underneath the lights of Broadway!

* Central Park, Riverside Park, Prospect Park, and Washington Square are some of my personal favorites here. Each provides a unique backdrop to your budding or blooming romance.

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