How to Ask Out Your Waitress

This is a quandary that has haunted me for years. Years, I tell you.

I think the quick and easy answer is that you develop a witty rapport with the waitress while she’s serving you, and she’s smiling and laughing and maybe touching your shoulder, and so it’s only natural that you slip her your number at the end of the meal and tell her that you’ll make her the best chocolate peanut butter pudding pie, way better than this restaurant’s desserts, should she ever call you.

But we all know that’s never going to happen.

Plus, not all waitresses are your waitress. That is, you may want to ask out a different waitress, not the one that’s serving you. You’re selecting things off the menu–why not select a woman to date as well! All you have is looks and general attentiveness to her patrons to go on, but that’s a decent start. Better than meeting a girl at a club and sizing her up by the length of her skirt and whether or not she can hear you over the din.

A few months ago, I thought I had figured it all out. This was soon after the breakup. Of course I’m not interested in actually dating anyone at this time, but I love the chase. The waitress in question was the hot one at Wasabi in Clayton (you know which one I’m talking about). I was wearing a distinctive tie that day (let’s say it’s a pink tie), so my plan was as follows:

  1. When the waitress is doing nothing, get up to go to the bathroom.
  2. Instead of going to the bathroom, sidle up to the waitress and get her attention.
  3. Say, “Hey, quick question. One of my friends wants to know if you’re single.”
  4. She asks, “Which one?”
  5. You say, “The one in the pink tie.”
  6. She looks over to your friends, then realizes–the hilarity–that you’re the one in the pink tie.
  7. She takes your tie in her hand, pulls you towards her, and makes out with you on the spot.

So that’s the plan. Foolproof, right? You avoid awkwardness if she has a boyfriend, and if she doesn’t, she thinks you’re clever and bold.

But there’s a problem. The problem is that you’ve taken away the greatest and least awkward excuse not to give someone your number: I have a boyfriend. You have to give her that chance after she knows who’s actually asking for her number, not before.

Why am I thinking about this? Again, I’m intentionally single and I want to remain that way. But there was a super cute and kind of alternative-looking waitress at Pueblo Solis tonight. More than cute. She was a hot hipster. Hipster is on my list of “must kiss” people (also on the list: every race except for white and Asian, a significantly older woman, a lesbian [current or former], Amy Adams, a nurse [during an appointment], and a beekeeper).

Of course, I did nothing, because I have no idea what to do and I’m not all that bold. I do know that you can’t have a friend talk to the waitress in question. Doesn’t work that way. You also can’t just write your number on a receipt. I’ve been a waiter, and you may not even know who wrote the number. Some sort of rapport or flirtation is necessary.

Is there a secret formula that I’m missing? Tell me, ladies and waitresses of the world: What is the right way to ask out your waitress?