How to legitimately surprise someone who’s celebrating at a restaurant
This post originally appeared in the July 31, 2024 edition of The Move, pro tips and advice from Eater’s dining experts, direct to your inbox. Subscribe now.
Years ago, I was celebrating my birthday dinner at a favorite restaurant of mine when, after our party had placed our order, but before the cocktails came, a server arrived tableside to present a bottle of sparkling wine. Before we were able to protest that we hadn’t ordered it, they explained that the bottle was “a gift from Amy” — a friend who lived clear across the country, and who’d casually asked about my birthday plans a few days before. It was a delightful surprise: I marveled at her sneakiness, turning what I thought was a friendly throwaway question into, in hindsight, a brilliant moment of reconnaissance. And because the bottle was something I wouldn’t have ordered for myself, it really helped prime our table for a night’s worth of celebration.
Call me old school, but the idea of Venmo-ing money as a present still feels awkward. Instead, inspired by this gift from years ago, the restaurant bottle-drop is something I’ve done for friends many times since. It’s a move that always satisfies.
Restaurants are usually more than happy to accommodate this request. It helps, of course, if there’s a reservation in your recipient’s name, and from there, it’s pretty easy: Check out the menu, pick out the item you want sent their way, then call ahead and ask for it to be delivered to that specific reservation; the restaurant will simply take your credit card over the phone. If you’re attempting this at a restaurant that’s walk-in only, enlist the help of a co-conspirator, whether it be a mutual friend, family member, or romantic partner, someone you know for a fact will be in their dining party — to ensure that they get seated, and to gauge that this is still a risk worth taking in light of any snafus that may arise while awaiting seating. (There’s nothing worse than arranging for a treat to arrive only for your friend to forego the hour-long wait and head somewhere else.)
I personally recommend a gift that arrives toward the beginning of the meal as opposed to sending dessert — which another person in the party may have plans for. Same for the similar move of picking up the whole tab: Doing so can create a weird dynamic for other guests in attendance who might have gone into the night planning to pitch in. And pragmatism aside, it’s also decidedly less thrilling: The one time I covered the bill outright, the recipient reciprocated by purchasing me a gift card to the restaurant for a similar amount; it started a war that’s still ongoing over picking up the check, surreptitiously or otherwise. (But also, don’t do this! Just let your friend pick up the check!)
The key to this move lies in creating a fun moment of surprise, giving your recipient that VIP feeling that comes with getting something sent to your table. I’ve done this not just with Champagne or a favorite bottle of wine, but also with a round of cocktails that I knew held personal meaning; I don’t see why something like a full seafood tower or a caviar add-on wouldn’t work just as well, if that aligns with your recipient’s interests. Use your judgment here — and if you’re unsure if your friend is drinking at the moment, or what their dietary preferences might be, getting a second opinion from a dining partner is always a safe play. But it’s a great way to add an exclamation point atop an already planned meal, one that says, “I want you to have a great time — on me.”
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