Date Night Ideas Trivia NYC: How a Random Tuesday Turned Into Something Unexpected

We’d done it all.

Dinner in Midtown, rooftop drinks in Brooklyn, a movie in Queens that neither of us remembered the plot of. After a while, every “date night” started to feel like a copy of the last. Comfortable, sure. But missing something. So when Tuesday rolled around and we had zero plans, I googled “date night ideas trivia NYC” half as a joke and half out of desperation.

Surprisingly, that’s how we ended up at Rabbit Hole Astoria—and honestly, I don’t think we’ve laughed that hard on a Tuesday in a long time.

The Setup: Zero Expectations, Full Curiosity

It wasn’t planned. We were in sweatshirts, not date clothes. The idea was just to grab a beer, maybe split something to eat, and see what this whole “trivia night” thing was about. I figured there’d be a few people, maybe a half-empty bar, and some background questions no one paid attention to.

Nope. Rabbit Hole had a full room, not in a packed or overwhelming way—more like everyone there was in on a secret we had just discovered. The kind of local crowd that shows up not because it’s trendy, but because it’s consistently fun.

When Trivia Night Becomes Date Night

I’ll admit it: I’m competitive. My partner is not. But the minute the host dropped the first round—TV couples from the early 2000s—they were in. We scribbled answers on paper like it was high school again, whispering guesses, side-eyeing the team next to us, and lowkey celebrating every right answer with way too much enthusiasm.

There was something about the casual competition, the themed drinks named after TV shows, the banter between rounds—it just worked. It was playful, low-stakes, and somehow way more intimate than a movie or another dinner.

Why It Works as a Date Night (Even on a Tuesday)

Here’s the thing: most “romantic” date night ideas in NYC feel like they’re trying too hard. Trivia night at Rabbit Hole? The opposite.

• You get to actually talk to each other

• There’s no pressure to be overly romantic

• You learn weird facts about your date (mine knew every single actor from The Office)

• And if the date’s going great—you stay. If it’s awkward? Trivia gives you an easy way out

Plus, the drink specials and bar bites make it feel like you’re out without blowing your budget. Which—let’s be honest—is rare in NYC.

What You Can Expect at Rabbit Hole Trivia Nights

• Trivia every Tuesday at 8PM

• New themes weekly (pop culture, music, TV, random knowledge)

• Cocktails and bar food you actually want to order again

• A crowd that’s friendly but competitive

• Zero entry fees, zero pretension—just good vibes and better questions

You don’t have to be a trivia nerd. You don’t even have to be good. But if you’re looking for new date night ideas, trivia in NYC might be your new go-to—and Rabbit Hole is a solid place to start.

When the Night Turns into a Weekly Thing

We didn’t expect to go back the next week. But we did. This time with friends. Then again, just the two of us. It turned into a little routine—a midweek pause button. The trivia became the excuse, but the real reason we returned was the way it made us feel: connected, low-pressure, and genuinely happy to be out together.

In a city like New York, finding something simple that feels special is a win. Especially when it comes to date nights.

So If You're Searching for “Date Night Ideas Trivia NYC”…

Try this:Skip the fancy stuff for a week.Text your person: “Wanna lose at trivia tonight?”Head to Astoria.Grab a cocktail at Rabbit. Laugh a little. Maybe win. Maybe lose.And leave feeling like you actually spent time together—without needing to plan a thing.