So you’re at a restaurant with a friend. At some point in the evening, perhaps in a lull in conversation between the removal of the plates formerly containing the rings of onion but before the presentation of the back ribs of baby, your friend leans over, gestures across the restaurant towards your server, and asks: “Pretty cute, right?”
And of course, your server is pretty cute. Plenty cute, in fact. And they seem really nice and sweet and charming. Even though you react in horror when your friend offers to exclaim, “MY BUDDY THINKS YOU’RE CUTE” when your server returns, a question flits across your mind: Is it okay to ask them out?
POINT: No, it’s not okay under any circumstances
Oh, you think your server’s cute? Congratulations—so did virtually everyone else they waited on today, and they’ve already had to deal with a barrage of unsolicited comments on their physical appearance, invasive questions about their personal life, high-larious innuendo-laden jokes pilfered from decade-old episodes of Entourage, and propositions beginning with the phrase, “What time do you get off… from work?” So why do you want to be a part of that?
The harsh reality is this: the basis of asking someone out is to explore a connection that you’ve made with them, and you probably didn’t make a connection with your server. The reason they seemed so sweet and charming? The reason they’re laughing at your jokes? The reason they’re not just saying hey, fuck off when you’re being all flirty with them? They want a good tip. Or, at least, they don’t want you to call over the manager and complain about how rude they were.
Because we insist on allowing the wildly outmoded system of tipping to be a thing, there’s an absurd asymmetry of power in the server-customer relationship that’s already fraught with tension. Don’t make it worse by making them worry that you’ll punish them with a shitty tip if they reject your advances or are otherwise insufficiently ego-stroking.
Look, there are plenty of wonderful, attractive people on whom you can hit who aren’t at work and aren’t just trying to get through their shift. Be considerate; don’t hit on people whose ability to make rent requires them to be a captive audience to you.
COUNTERPOINT: Yes, it’s okay as long as you’re polite
Let’s not exaggerate what we’re talking about here: it’s just a polite invitation to coffee at the end of your meal. If your server is old enough to have a job, your server is old enough to deal with this basic, mundane social interaction without it ruining their day.
That’s not to say that some customers can’t be total pieces of shit about it, and there’s no excuse for that. But it does no one any good to define “inconsiderate” down to such an extent that considerate people start to internalize the idea that merely asking someone out is an untenable imposition. Asking someone out at their work is less than ideal, to be sure, but it’s hardly a sin.
Let’s be real: plenty of people have gone on dates with their servers. It could be that your server is just being friendly and gunning for a tip, but maybe they actually like you and think you’re cute. Both are possibilities, but why assume when you can know for sure? It’s not like your server is really in a position to ask you out.
Here’s the bottom line: Your server is an adult (…seriously, they are, right?). They should be able to handle a polite date request. Ours is a society where people are generally expected to find love and be in relationships, and that means sometimes people will ask other people out. Nobody should have to deal with assholes, of course, but polite invitations to coffee? That’s just a part of living in a world with other human beings.
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If you’re going to ask your server out anyway
Be polite. Don’t be cocky, gross, creepy, or sexual—they’ve already likely heard all of that shit, and there’s a good chance they’ve already heard it earlier that day. (“But this one time my buddy Gizmo told this joke about titties and totally hooked up with our server!” Yeah, I know, some people inexplicably reward being a creep; it doesn’t make it okay to be creepy.)
Don’t monopolize their time. It’s understandable to want to build a rapport with your server so that you don’t seem like just another customer. Sometimes it works. But most of the time, you’re just making them squirm because they’ve got work to do and they don’t know how to extricate themselves from customers who are transparently hitting on them. If anything, take their lead: if they don’t seem chatty after you ask them how their day is going or what appetizer they recommend, don’t push it.
Ask them out after you’ve tipped. You can at least remove the “Is this going to adversely affect my tip?” aspect of the situation from the equation. Also: tip well (it varies, but it’s normally around 20 to 25 percent for dinner or brunch; 25 to 30 percent for a weekday lunch), but not absurdly well—it could be construed as trying to purchase a date with them.
Don’t be loud or ostentatious about it. In particular, don’t let other tables or their coworkers hear—being asked out in front of an audience is really uncomfortable. Plus, it sucks to be embarrassed in front of coworkers; they have to see those jerks every day, you know.
Take no for an answer. Understand that, because of the aforementioned asymmetry in the server-customer dynamic, your server may find a way to turn you down that sounds friendly, playful, or equivocal. If you don’t get an unmistakable “yes,” then you should take it as a “no.” Make sure you signal that you fully accept and understand it’s a “no” so that your server doesn’t think you’re a creep who will, like, follow them into the parking lot or whatever.
Consider asking them out with a note. It’s more passive and middle-schoolie than most people are comfortable with, but it’s actually a particularly considerate way to ask out your server: it avoids an awkward conversation, it’s private and audience-less, and if they’re not interested, they can easily turn you down with a pocket veto. Many—though, it should be noted, not all—people would appreciate that sort of thoughtfulness. (If you do this, you should probably assume that they’re not going to call instead of, say, constantly checking your phone. If you know you’re the type who will constantly check your phone, seriously: don’t do this.)
Use common sense. You’re 45, and your server looks like they’re taking an extra shift to pay for senior prom? Come on now.