Ask The Salty Waitress: What Should I Consider Before Proposing In A Restaurant?

Dear Salty: As Valentine's Day approaches, I'm preparing to propose to my long-time girlfriend. But I'm stuck trying to figure out where to pop the question. We're both kind of foodies, and I splurged for our first date, at a nice restaurant that has since become our go-to place for birthday dinners. It would the perfect spot, so I'm leaning that way.

But I can't really get a handle on whether this is best option or not. Of course, none of my friends are going to be like, "Yeah, my wife really wishes I'd done it at the Empire State Building instead." You seem to have a lot of restaurant experience, so I'm asking you; have you seen a lot of restaurant proposals? Do you have any ideas for do's and don'ts: What should I do, and what should I absolutely avoid?

Thanks,Temporary Bachelor

Dear TB,

Have I seen a lot of restaurant proposals! I've even seen some at my own beloved diner. Some people can really get romantic over a Denver omelette and hash browns.

For you, though, I think going to your favorite swanky spot to do the deed is a lovely idea. It's a place where you have sentimental attachment, and that will likely mean a lot to your about-to-be-betrothed. Still, the restaurant proposal brings up a multitude of issues. So I talked to Jeff Witzig, manager at Topolobampo, Rick Bayless' acclaimed Mexican restaurant in Chicago, who was a font of information regarding using the restaurant setting for this particular life change. So between Jeff and myself, here's a quick guide on what to do and what not to do regarding restaurant proposals. If you only walk away with one tip, it's this: Keep the ring out of the food, buddy. But first:

Tell the restaurant

If this is a place you usually frequent, call the manager or stop by and visit your favorite server and give them a heads-up. You don't want to spend your magical evening stuck at a table by the bathroom, or smack dab in the middle of the floor for all to see. A cozy, corner table by the window would be ideal. Getting seated off to side also helps prevent your future public embarrassment in case—I know, it's too horrible think about, I'm just hedging all bets here, but how do I put this—she does not answer in the affirmative.


Jeff seconds this notion, and stresses that you call and at least visit the restaurant first. "That's very, very helpful for me if they have some idea of what they can do and then they ask is this possible." If you don't have a plan, Jeff says he then gets thrust into the role of event planner, "and that is challenging, because I don't know them or their partner to figure out what would they be special to them. So my main thing is if they have an idea, and then we can have a conversation about our capacities as a restaurant."

What sorts of things do people ask for? Jeff says that table location is "no big deal," flowers and candles are a given, but then things can get complicated. He points to frequent requests for "special musicians," and in a small space, a mariachi band or string quartet can make thing uncomfortably crowded for your fellow diners, who are also out to have a good time and enjoy their evening. It's your big night, but it might be someone else's big night too, y'know? That couple celebrating their 50th wedding anniversary may actually trump your sweet little proposal. So while I'm sure your mind is consumed right now by this big life step you're about to take, please remember that it's not all about you, even at your selected proposal setting.


Don’t ask in the middle of your meal 

Timing is key. While you hate to think about the possible negative response, it could happen, and then you have to have an escape plan. Jeff describes, "We've had people that have suddenly needed the check because the proposal didn't go well." Can you imagine the anguish of sitting there waiting for the credit card to run?


Still, some diners are committed, no matter what answer they get. Jeff remembers a couple that "was an obvious no, and then they did complete their meal, but it was in complete silence. And we're a multi-course [restaurant], so we're going in every 10 minutes to clear silverware and plateware and introducing new dishes and new wines to people who are essentially looking down at the plates. Their relationship was dead in the water." I think it's a pretty big nod toward Topolobombo's excellent food that the couple remained through several silent courses.

The down-on-one-knee question

But if you are pretty sure about her response and don't mind a multitude of of public attention, go ahead, get on your knee. After all, if a man does that in public, he's either becoming a knight in King Arthur's court or is proposing to his girlfriend (let's leave the NFL out of things for now). So that one maneuver is going to immediately draw the eyes of everyone else in the restaurant. It's up to you whether you want them all in on your big moment. Speaking for myself, Salty's a traditionalist—crusty, but with a heart of gold—so I always do a happy little gasp when I see someone going for matrimony in a big way in public. I am the first to clap wildly and dab my eyes with my mustard-stained rag. It's not often that we get to see the big life moments of total strangers in the real world; no one's inviting us to random delivery rooms or anything, are they?


Jeff agrees. "The knee draws everybody's attention," but he also points to a very practical reason to keep this tradition intact: It enables a hopefully non-awkward transition to a post-proposal embrace, which would be harder to do across a table. "After a proposal, you usually want to hug and kiss the person, and I've seen it where across the table, it's kind of awkward to be seated. Plus there's a candle between you—it's a fire hazard." Excellent point! "So in a restaurant, I'm in favor of the knee just for that transition."

But if you don't want to be the story everyone else is going to talk about for the rest of the night, just stay in your chair, take both her hands, and have the ring at the ready at dessert time. You'll soon get an answer to the big question either way. Just watch that candle.


Do not put the ring in the food

I don't know where the idea to hide that ring in the dessert first came from, but it's terrible. You do not want the symbol of your lifelong devotion to become a choking hazard, or worse, to have it travel through your future wife's digestive tract. I swear this happened to a friend of mine, and I got skeeved out every time I looked at her ring, imagining where it had been, the things it had seen.


Having seen his share of rings in desserts, Jeff describes this experience as "very messy." To try to avoid scraping whipped cream out of a diamond setting for all eternity, some proposers are putting the ring in plastic first. But, Jeff notes, "having a plastic-wrapped ring in a piece of cake at the end—is that really the kind of mechanics you want to go through?" Advises Jeff, "Keep the ring in the box."

If you must, have the ring served alongside the dessert on a tray or something. But do you really want something that cost two month's salary out of your sight for any extended period of time? She's (hopefully) going to love it whenever you show it to her, even if you just slide it across the table: When it comes to an engagement ring, it's not about the presentation. A Denver omelette is an entirely different matter.


Should this be a surprise? 

This is a very particular decision. Does your partner kick your shin when those "Every Kiss Begins With Kay" commercials come on? Is she talking a lot about her friends' engagements/proposals/rings/dresses? Has she recently queried whether your parents have ever been to the Caribbean and if they have passports? (She may be thinking destination wedding.) Since you guys have been together for so many years, unless she (yes, or he, it's 2019) has made her anti-nuptial feelings perfectly clear (perhaps a "forever single" tattoo on her forearm or similar), I'd be surprised if the issue of marriage hadn't come up before this. If it hasn't, be sure to test the waters before the big day. You don't have to let the giant sparkly cat completely out of the bag, but a discussion about your respective futures (stay or relocate? kids or no?) is necessary if you haven't had one yet. Says Jeff: "Even with as much pressure as it is, with my staff, we're so excited to see it happen. So when it is a no, it kind of sucks the air right out of the environment. While you can't always predict that, having enough conversations with your partner helps take off some of that pressure."


On the other hand, if you're already ring-shopping, all bets are off. It's a good move on your part to let her cast an opinion on that ring she'll be sporting for the rest of her life. But sometime guys can hit it out of the park without help: My second husband did that, a lovely two-carat emerald cut that I later hocked for the down payment on a Chevy Nova.

Which I bring up to stress this, if you'll allow me a little Salty indulgence: Right now, you're at the beginning of a beautiful journey. Your collective life is stretching out ahead of you like an all-day sucker. These decisions you agonize over now—the engagement setting, and then all the bizillion wedding details that will follow if things go your way—will be long forgotten by the time you guys are fighting over whose turn it is to change the midnight diaper and where in Florida you should purchase your retirement condo.


Think long-term, big-picture, is what I'm saying; life throws a multitude of turns at you at ever given opportunity, and who knows where things will end up eventually? So at this moment, the really important part is not the restaurant, the dessert, or even the ring. It's this person. Mazel tov. Oh, I think I have something in my eye—where's that towel?