Flirting with Waitresses 12/2/18


By Richard E. Bleil, Ph.D.

One of my enjoyments is eating at restaurants. It’s not so much the food as just getting out into the world, leaving the office, and interacting with people. As such, tend towards those restaurants with friendly staff. And, frankly, I like it when waitresses (and waiters, although this story deals with a waitress) takes the time to chat with me. And, yes, in full confession, if it seems a waitress is flirting with me, I may ask her out.

Okay, right now, there’s a good chance that you, the reader, has a little voice in your head saying, “the waitresses only flirt with you to get a bigger tip, dummy.” I get this. I also understand that flirtatious behavior is not a license to harass. But, in my defense, if a waitress is so good at flirting (or “being friendly”, as is most likely the case), then the only way for me to find out if there is more of a connection is…brace yourself…to ask.

Now, having said that, and now that you know that I have asked in the past, let me quickly add that if she is not interested, then the burden falls to me to stop. Yes, stop. Not talking, not being friendly, but the responsibility is to accept her answer, in a friendly and non-threatening manner, and move on.

That’s the part with which so many men have difficulty, and, frankly, the topic of this story. See, she was a very lovely waitress at a restaurant and bar. She would always chat with me, laugh with me, share stories, and sometimes even sit with me when she wasn’t otherwise busy (one of my favorite things since I typically eat alone). To give you some background, she was also a professional cheerleader, so physically she was in great shape, and very attractive, which I tell you so you understand the direction this will eventually go. And, frankly, we really did “click”.

So, yes, I took a chance. And, no, she was not interested. She turned me down in a very sweet manner, telling me she already had a boyfriend, but I’m guessing she really just was not interested. And, that’s okay. I never asked again, but continued to frequent the restaurant, and our relationship never changed. I accepted her response, knew it was not ill intentioned, and moved on.

Time passes. We always said “hi” when I was there during one of her shifts, whether she was my waitress/waiter or not, and we still talked regularly. Frankly, I thought of her as my friend, and still do today.

So, one day, I’m having a meal, and she is working at the bar. Our relationship (by that, I mean friendship; not every “relationship” has to have a romantic or physical component, y’know) had developed to the point that she would even “unload” on me when she needed to vent. And, sure enough, as i’m enjoying a lovely meal, she sits down opposite of me, clearly unhappy.

I ask her what’s up, and she tells me how she hates guys who can’t take “no” for an answer, and she wasn’t even talking about me! Apparently, there was a man at the bar who was hitting on her. As her friend, I had to do that thing that, for some reason, is so difficult for men; I had to listen and not try to “fix” it.

She vented, I listened, and I think I helped. She seemed a little more relaxed by the time she left the table, but, sadly, did have to return to the bar and that customer, but I think she was in a better frame of mind to handle it.

Then it occurred to me. Here is a wonderful young woman, attractive, yes, but also very intelligent, very interesting, with a rich personal history, wonderful insight, and just a great person. She had, at that time, two men who wanted to spend time with her, the patron at the bar who was merely interested in her appearance, and me, who enjoyed our conversations and connection. He was pressuring her, unable to take “no” as an answer. I accepted any time she spent with me as a gift.

So who won? Well, the reality is that, at that moment, I was the one with whom she was spending time.

It’s a difficult lesson for men to learn. If you will forgive the analogy, it reminds me of a quote about a butterfly. If you chase it, it will run from you, but when you calmly sit down, and remain still, she might just land on your shoulder.

2 thoughts on “Flirting with Waitresses 12/2/18

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