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Overworked waitress doesn't need any guff from overly entitled diners, she raps.
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Overworked waitress doesn’t need any guff from overly entitled diners, she raps.
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I get it, waitresses are being all nice and [bleep] ’cause it’s their job and they want a fat tip. But let’s pretend that you are seriously interested in your waitress. Is it rude to show interest or solicit a date or more info from someone who is working? If it’s not, what are some ways you can approach that topic? —Question via Reddit, edited for length

THREE ANSWERS

Host of “Fred and Angi in the Morning” on 103.5 KISS-FM

Fred

Host of “Fred and Angi in the Morning” on 103.5 KISS-FM | Single | 35 | @fredonair

While I would not say every friendly service industry member is after you for your fat pockets, it probably is fair to assume as a general rule that most wouldn’t want you to confuse their friendliness with romantic interest. Great bartenders and servers are attentive, amiable and, sure, when appropriate, perhaps a bit flirtatious. You have to remember in whatever approach you decide (to ask or not to ask for a date) that these people are at work and are there to make money—this isn’t your own personal Tinder in 3-D. So keep in mind a few things if you ask your waitress out: 1) You probably will not hear from her. 2) If she gives you her number, it may be fake. 3) You may at some point return to the venue, so be cool regardless of what happens. Consider that whatever you do, the amount of fun you have and the quality of service you receive at her place of employment could be significantly affected by your behavior. An easy way to circumnavigate any adverse affects of your attempted restaurant romance is to follow the not-often-talked-about golden rule: Only hit on people at bars you don’t frequent.

Courtney Jacquin

Writer and editor
Writer and editor

Writer and editor | In a relationship | 24 | @courtneyjacquin

Hi! First off, you seem lovely. Oh wait. Let’s take a moment to talk about your server being nice because “they want a fat tip.” Did you know that, according to a 2014 study from the Economic Policy Institute, tipped workers have a median wage (including tips) of $10.22, compared with $16.48 for all workers? So, y’know, they’re actually just trying to make a living that’s, on average, worse than others’. Second, contrary to popular belief, women are not objects constantly vying for the attention of ogling onlookers, hoping to be asked out on a date. She’s just doing her job. If someone walked into your office job and walked up to your desk and asked you out, it would be a little weird, right? So for the most part, please do not do this. In some rare, rare instances, if you really have a connection with your server and have a really meaningful conversation beyond the specials of the day and the weather, maybe leave your number and a nice note with that aforementioned fat tip and leave it up to her.

Morgan Olsen

RedEye Eat & Drink, Lifestyles editor
RedEye Eat & Drink, Lifestyles editor

RedEye Eat & Drink, Lifestyles editor | In a relationship | 28 | @morgancolsen

There’s a very real chance that your waitress doesn’t want to be hit on or, worse, solicited while she’s trying to do her job. I wouldn’t recommend asking her out on the spot or pushing the issue in her workplace. She presumably goes to work every day to make a living, not to find her soulmate. And just because she’s working your table doesn’t mean she’s a captive audience for you to flirt with. Take it to a bar or, better yet, a dating app if you’re looking for a match.

Thanks for reading “Threesome.” Each week, we take a look at a relationship question from the public and have three panelists give their insights. Have a question to ask? Shoot it over to us on Twitter at @redeyechicago or on our Facebook page. If it’s a little more private, feel free to email it to redeye@redeyechicago.com with the word “Threesome” in the subject line.