Q&A: How Do I Ask Out the Waitress Who Serves Me Every week?

Dear Juliette,

I have a really big crush on the waitress who serves me every week at a restaurant I go to. I can’t tell if she likes me or if she is just being nice to me because it’s her job. How can I tell if she wants me to ask her out or if I should keep my mouth shut so I can keep going there?

My Dear Reader,

I am a firm believer that prolonged eye contact is a giveaway. As a former waitress, I rarely made eye contact for longer than a second with any of my customers for the specific reason that I dreaded any of them asking me out and making it awkward thereafter when I inevitably said no. I only made real eye contact with the guys who I was truly interested in, the ones who I wanted to ask me out. I have tried to make this a rule in my life in the fashion world as well, due to being so outstandingly magnificent that every guy who meets me wants to go out with me. It is not a guarantee, but if she looks directly into your eyes, longer than she needs to, there might be something there. With me, if I linger, there is.

bmovieContrarily, if she is shy she might have trouble looking at you, but if she is being gushy and awkward that is also a pretty good sign that you make her nervous. If she giggles with her co-workers after walking away from you, plays with her hair while talking to you, or any other cliché schoolgirl behavior ensues, you probably have a pretty good chance. As much as some waitresses “work it” for tips, most waitresses are real people who still maintain at least 75% of their personality while working. I did.

If you feel comfortable asking her co-workers about her, do it. They will be able to give you the best idea of what her status is and you can read whether they encourage or discourage you to go for it since they probably know more about her than you do. They might even have ideas for where you should take her or things she likes. Do a bit of recon before you throw it all out there. It might be as easy as finding out that she told someone she has a crush on you, and then you just have to decide the best way to knock her socks off with your chivalrous, sweet, charming greatness.


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