New York Style Romance, $20 or Less

Or, #28. “Show him you can have fun on a cheap date—but don’t overdo it!”

The economy. It’s all anyone talks about these days. The reason? It’s bad. Eggs are expensive, stocks are in free fall, Forever 21 is bankrupt (again). It seems like we’re staying afloat—the canary in the 21st-century economic coal mine will sing when the Costco hot dog costs more than $1.50—but still, holes are springing up all over the boat, and water is starting to pour in.

I know what you’re thinking. “Emily, you are no economist, back in your lane.” Or, “This Substack is about dating and adventures! If I wanted a panic attack I’d turn on MSNBC.” Or maybe even, “Didn’t you get an E in accounting?”

These are valid points. My rebuttal (to the imaginary mob coming for my financial credibility) is that dating and the economy are inherently intertwined. One might argue they go hand in hand.

According to MassMutual.com, “The average American spends roughly $168 per month—or $121,000 during the course of their lifetime dating.” This was from 2022, so we can imagine that just like the cost of living, this number has increased. In that same article, a poll by MassMutual (they didn’t pay me for this, I promise) revealed that nearly one-third (29%) of singles said their financial situation had deterred them from dating or getting in a relationship. Young adults (41% of millennials) were most likely to indicate that their finances kept them from dating seriously.

The financials of dating are astounding. Think about drinks alone: in New York, a cocktail goes for $24, and if it's a good night, you’re not just having one. To be actively going on first, second, and third dates—which may or may not turn into anything—and continuously pulling out all the stops, giving the old razzle dazzle at every bar and restaurant in town, can be financially and literally exhausting.

So how can you make romance feel special in a city (and an economy) that gets more and more costly by the day?

Behold, #28. “Show him you can have fun on a cheap date—but don’t overdo it!”

Think of this as a Choose-Your-Own-Adventure to a perfect inexpensive date. If you’re not in New York, you can use this template and sub in options for your own city. Feel free to start at any given time, but this is technically intended to be done from 11:00 am to 11:00 pm, Broad City style. Just because you’re on a budget doesn’t mean you can’t ball out for a 12-hour day! So ignore the part about not overdoing it. This definitely does, and it’s worth it. Without further ado…

---

A CHEAP DATE

11:00 am

Coffee in the park (winter alt: a hotel lobby, ideally with a fireplace). If you’re really trying to achieve zero spend, suggest a location within walking distance of your apartment, otherwise MTA will hit you with a fat $2.90.

As for the drinks, send your date a gushing text about your new coffee maker and beg them to let you bring a freshly brewed espresso. They’ll jump at the offer and see you as someone who is not only budget-savvy but also a responsible adult. That’s hot!

A quick financial heads up: you’ll need to get reusable cups, espresso beans, specialty milk, a flavored syrup if you’re classy, and if you don’t own an espresso machine, they start around $30 (Bialetti Moka Express) and run up to around $5,900 (La Marzocco Linea Mini).

After coffee, take a walk in the park (or around the hotel lobby).

1:00 pm

Omg… that went so well! Time flew and now you’re hungry—or is that just butterflies? Either way, a bite seems like the next reasonable activity. But it’s certainly not the cheapest.

Unless you’re RICH, here’s what you do next:

Quickly develop a street act (two-person show, close-up magic, singing either very well or so badly people pay you to stop, or finding Billy Eichner mid-episode of Billy on the Street and get a “for a dollar!” question right.) Spend no more than thirty minutes rehearsing, then parlay your talent into somewhere between $15 and $20. Quit after that—not because you’re not good enough, you’ve got a real future, but because you have a date to dine with! Eyes on the prize!

Eating out is unquestionably expensive in New York, but there are ways to do it inexpensively. Often some of the best food costs the least. Many of The New York Times Best 100 Restaurants feature menus where two could reasonably get a meal for under $20. Take, for example, #10: La Piraña Lechonera, a Puerto Rican restaurant run out of a trailer in the Bronx, offering pork and rice for $14. If you’re not a purveyor of the Times, hop down to Chinatown and wander into a Dim Sum spot with dumplings for a few dollars. And then, of course, there’s the classic dollar slice—actually somewhere between $1.50 and $2.00—but still a steal.

If all else fails, head to the two-story Burger King in FiDi. On the right day you could stumble into a writing workshop hosted by Dream Baby Press. A few kids meals should be on budget. Plus, you get a toy!

Another financial heads up: At some point, you may need to use transit to get around. That’s life. Factor that into your funds.

3:00 pm

The food was fast; the meal was not. You picked over scraps while staring into each other’s eyes, getting deeper and deeper into the date. Now at hour four, you could call it and make plans to see each other again soon. That would be perfectly acceptable. Normal, even.

Not everyone is normal. Onward.

By now, you know each other well enough to engage in some gameplay. Hey! Get your head out of the gutter! You’re going to a vintage and/or thrift store for a movie montage dress-up. Nothing more.

In any given neighborhood, you could throw a penny and hit a thrift shop. And if it landed inside, they’d probably resell that penny as a “vintage street coin” for $5. And I’d probably buy it!

New York City thrift shops are a true treasure trove. I’ve heard that the Goodwill on Upper East carries designer bags, and the Housing Works Park Slope is a coverall lover’s dream. Urban Jungle in Bushwick offers everything from cowboy cosplay to Margaritaville chic. And Screaming Mimis in the Village sells more sequins than even ABBA could bear.

Here’s where the fun comes in. Give each other scenarios to dress for. “You’re going on vacation with your new stepkids, and they hate you.” “You’re about to commit a major heist at the Medieval Times in New Jersey.” “You’re a 19th-century vampire just trying to make it work in 1977.”

These are a few ideas to get you started, but please be creative. Carry on for as long as is fun or until someone from the store politely asks you to leave. (Alternatively, they may ask to join in. The last time I played, we stayed for an hour and became close personal friends with the staff).

5:00 pm

Admin time. You’ve been on this date since 11 am, take a minute to check in with your family, friends, and pets. Just because you’re having the time of your life doesn’t mean you can ghost your people! Tell them what’s up and send a video of you marching around Beacon's Closet dressed as a 1990s power banker who wants to give it all up and go to clown school.

5:30 pm

You’re hungry, you’re thirsty, the staff at the store let you keep the outfits because you “made it weird” and “ripped them beyond repair after that cartwheel.” Time to make like Marnie and Charlie in Season 5, Episode 9 of Girls—masterpiece “The Panic in Central Park” —and use this fancy dress for all it’s worth.

Head uptown to Met. Hopefully it’s a Friday or a Saturday, because that’s date night. Really. The Met offers live music, drinks, and special programming from 5 to 9 pm on weekends. In the warmer months, the roof is also open. There’s a bar and a band and a packed house of art-loving aficionados basking in the sunset. This event is free with museum admission, which is Pay What You Wish for NY state residents and NY, NJ, and CT students with valid IDs. So if you have extra cash from the street act, put a few dollars in. But also, do what you must.

If you want to drink, you and your date must embark on a challenge: charm your way into a free cocktail from a smitten stranger! Of course, there is the possibility that either you or your date hit it off with the drink purchaser and they fall in love and leave you in the dust. But if that happens, it’s a sweet story for them and a risk you have to be willing to take.

7:30 pm

Provided your date hasn’t left you for the soda savior on the roof, you can exit the Met. You’ve spent nearly eight hours together; it has not broken the bank. Cool!

You wander down the museum’s marble steps and into Central Park. Your hands knock against each other as a nervous energy fills the air. You interlace a finger. Then another. Then another, until you’re walking hand in hand by the Great Lawn. The park is filled with sounds of evening delight: a popped bottle of champagne, peals of laughter from friends on the grass, a barking dog chasing a squirrel, elderly men practicing Tai Chi under a tree.

Then… music? A jazz musician wailing on his saxophone in the arches of the Bethesda Terrace. Or if it’s summer, it might be a Summerstage concert at Rumsey Playfield, offering free (and ticketed) shows. If it’s August 2025, it’s possibly decorated actors performing Twelfth Night for Shakespeare in the Park at the newly reopened Delacorte Theater. And if it’s a nightmare, it could be James Corden reviving the Late Late Show with a fully staged crosswalk musical at the intersection of West 79th and West Drive.

Let’s pretend it’s a jazz musician. You sit by the fountain as the sky turns from dusk to dark.

You buy an ice cream from the cart. Yeah, we’re having dessert before dinner. Yeah, we’re spending money now. (If you’re strapped, do the street act again, then pick this up.) The music scores your moment as you finish the cone and wipe a bit of drizzled chocolate off your date’s face.

You look up at the stars. You can’t see many, but you’re surprised to see a few. You lean into each other and gasp as a comet flies by. Oh, wait, never mind. That was the asteroid headed for—

Kidding. But what a way to go, right?

9:00 pm

Hands held tightly, you amble out of Frederick Law Olmstead’s wooded oasis. You and your date feel worlds away until suddenly, you hear cars whizzing by and see pedestrians scurrying across 59th and 5th. You slip back into reality.

Or maybe you don’t. Maybe you say fuck it and sweep each other up into a big romantic New York City kiss. A New York City kiss is a perfect smooch that is inevitably ruined by being splashed by a puddle, a leering man shouting “me next,” a too-friendly dog, or getting in the way of Richard Kind (happens more often than you’d think).

9:05 pm

The grumbling stomachs are too much to bear. It’s time to eat.

You could do it together—go to a diner that may or may not actually have diner prices (Cobble Hill Coffee Shop, Tom’s, Square, Kellogg’s, Pearl). Or you could go back to your apartment and serve up a steaming plate of spaghetti aglio e olio, the three-ingredient dish cooked by Jon Favreau for Scarlett Johansson in the movie Chef (arguably one of the most sensual cooking scenes ever filmed).

You could also call it a night, shake hands like adults, and go back to your respective homes for leftovers or whatever waits in your fridge.

As for me? Once we’ve gotten through the first ten hours and are sufficiently hooked, there’s only one reasonable next step: demand the nine-course tasting menu at Per Se.

11:00 pm

Go to bed! Whatever that means… ;)