The perfect date night begins with a game of Delivery Roulette

The best way to get to know someone is to have them order food for you.

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Takeout container of delivery Pad Thai
Photo: Erin Clark/The Boston Globe (Getty Images)

Dating during a pandemic is a unique experience. When my current boyfriend first slid into my DMs in April 2020, we assumed that it would be no time before we could casually grab a drink to get to know each other. After a couple weeks of texting, as the pandemic got worse and worse, it became clear that we would have to put a hold on our first in-person cocktail—both trying to be as safe as possible, we stuck to just chatting over FaceTime for the early stages of our relationship. But just because we couldn’t go on a traditional dinner date didn’t mean we couldn’t make meals part of the fun.

Delivery roulette is simple. Get your date’s address for delivery, see what’s nearby, then send them dinner without telling them what’s coming. They’ll do the same for you, and when the food arrives you hop on the digital video platform of your choice, unbox your meal, and go from there. You can ask a few questions ahead of time to make sure there are no complete disasters: deathly allergies, dietary restrictions, any ingredients that are a complete no-go. But don’t give too much away, because the real joy is in the surprise.

My boyfriend and I first tried this out after a few FaceTime chats and a handful of Netflix Parties (another great form of digital hangout that’s reminiscent of the golden days of AOL Instant Messenger). I spotted the idea on TikTok and, always desperate to be a hip TikTok teen, thought we could try it out. We’d had enough time to get to know a little bit about each other and put that knowledge to the test. Reader, we both nailed it.

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I sent him a meal from his favorite barbecue place complete with a bottle of their signature sauce, remembering that he had sung its praises in one of our earlier talks. He sent me a meal from a restaurant near an old, beloved apartment of mine, a spot that I hadn’t even considered would be within my current delivery radius. We not only both enjoyed delicious meals but were able to acknowledge how the other was paying attention and taking interest in our lives.

The meals don’t always have to be so personally aligned to your partner, though. Delivery roulette can be a great way to simply try something new and get you out of your delivery rut. On another occasion, I was sent an incredible jibarito from a neighborhood spot that I had never bothered to try—it soon became a new go-to.

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Plus, you just might learn more about the other person in the process. On a whim during one delivery roulette night, I sent my boyfriend a bowl of Caldo Gallego soup from a local Cuban cafe. When he received it he was shocked, revealing personal and family memories based on the soup that may not have come up in our conversations otherwise.

We’ve been together for almost two years, and while we are now fully comfortable with seeing each other in person and even dining out at the occasional restaurant, we still keep delivery roulette in our back pocket. Snowed in at our separate apartments? Delivery roulette. Someone’s got a case of the sniffles? Delivery roulette. Spending time in a different city? Delivery roulette! It’s the perfect distanced date idea for every occasion that really proves that the way to someone’s heart is through their stomach.