How To Flirt With Your Server

As a single man in his thirties, I can attest to the fact that it is difficult to meet people in a modern world.  It is tough to meet people in a highly cynical and technological society.  Dating co-workers is wrought with pitfalls and in social settings people move in intimidating packs.  As your social circles begin to fill with spouses and children, not even parties are safe places to approach people.  This often leads to taking advantage of any opportunity to engage someone in conversation as a chance to flirt.  Inevitably this leads those on a search for a soul mate (or something less profound) to flirt with their server.

Over the years I have seen this happen countless times.  A vast majority of these attempts fail.  I have seen everything from bringing flowers (fail) to large group serenades (epic fail) result in embarrassing disaster.  I also have heard tales of success. I have witnessed co-workers giddily gossiping about the handsome man who gave them their number.  While flirting with a server generally results in failure, it occasionally succeeds.  This made me wonder what the keys to success were.

As a single man in his thirties, I admit that I am no expert on the topic.  Did I mention that both of the fails above were mine?  This is why I consulted a random sampling of some of Kansas City’s most attractive waitresses to find an answer.  Those that didn’t think this was a thinly veiled attempt to flirt with them gave me some incredible feedback.  So in an attempt to share this information with the masses and provide a slightly more interesting than normal blog post, I share with you the “fails” and “wins” of flirting with a server.

I start with fails because this was a longer list for each of them.  Servers did not come into work to meet you.  They have a job to do and your best efforts to flirt often make that job more difficult.  Any misstep can ruin your chances.  Before you worry about what to do, avoid shooting yourself in the foot with any of these moves.

Do Not:

Continuously flirt obviously throughout the meal

Look like you are showing off for your friends

Disappear to the bathroom to remove your wedding ring

Discuss money or finances at the table

Name drop

Call the server “honey,” “sweetie,” “babe,” or “stud”

Show up repeatedly during their shifts

Call the restaurant to see if they are working

Have a friend ask them out for you

Leave your number on the credit card receipt

Leave a bad tip

Leave such a good tip with the idea that will bribe them.

Have ten fraternity brothers join you in drunkenly serenading her with “You Lost that Loving Feeling.” (trust me)

That is by no means a comprehensive list.  Social awkwardness and fully stocked bars lead to people coming up with new and creative ways daily to blow any chance they may have.  There is hope though.  While the “Do Not” list was longer for everyone I consulted, they almost universally agreed on several moves that will improve your chances.  Here was their advice.


Wait until after the meal

Approach them away from the table

Be subtle

Make a sincere and specific compliment

Leave them your number

Leave a nice note instead of the generic “call me”

Leave your name

Leave a good tip


Exit the restaurant afterwards

This list is in no way a guarantee of success.  Chemistry and attraction play a huge role in all such matters.  This is nothing more than a helpful guide to succeeding when those things are already working in your favor.  Be classy and respectful above all else.  They are there to do a job.  Respect that at all times.  I hope this shed a little light on the topic for those who read it.  As for me, I swore off trying to flirt with waitresses sometime during the second off key verse of that horrible song.

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5 comments on “How To Flirt With Your Server

  1. yellowcat on said:

    A little friendly banter is a good thing and it makes my day a little more fun, but I don’t want to date a customer. I don’t go to where they work and sexually harass them, I expect the same thing.

    And guys: When you constantly come in on a server’s shift, it isn’t endearing. It’s creepy. The flowers and gifts usually go home with a different server who has fished them out of the trash. The entire staff (back of the house, too) laughs at your desperate attempts to get someone waaay out of your league. We also make note of your visits in case police intervention is needed.

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