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.

Read the full post at RestaurantLaughs