The idea of trying again to approach her for social reasons did not appeal to me at all as I thought along those lines of cutting her loose. That's because I have BAD associations with persistence of that nature coming from me towards someone such as this waitress. I associate persistence with obsession and obsessive pursuit and chasing someone to the ends of the earth and back.
The problem with thinking like that resides in the fact that I have encountered stories from celebrities in the media telling of their personal dating and relationship experiences where the man DID persist and DID succeed, and a relationship ensued. Jane Fonda told of how Ted Turner got her number from someone, called her several times, asked her out several times, and after some attempts by Ted, she "gave in" and went out with him, and they dated and were married for some time.
These kinds of stories really messed with my head, because that was definitely NOT my experience with persistence. I would tell myself, "I'm not some hotshot rich guy, or athlete, or rock star, so I have to play by a different set of rules than a Ted Turner plays by." By "I would tell myself" stuff like that in the past, I mean the past as of this past several weeks or so.
I rolled this around in my head a bit. I now think some persistence can work, provided it doesn't degenerate into the crazy, chase-them-to-the-ends-of-the-earth-and-back type of persistence that I would engage in when I was a lot younger. I'll take that notion under advisement as I contemplate going to this waitresses' place of employment and talking to her some.
I believe that as long as someone such as this waitress likes me on some level, and as long as I'm really "easy" in the way I go about approaching her for social reasons more than one time, she might even be okay with a bit of persistence from me. I don't even know if this waitress is even single, but if she likes me as a customer and an acquaintance enough, it might even be okay to approach her more than once.
I think about a couple of women who came to my table at the MoCCA Fest comic book convention in New York City in years past. One, in 2012, hung around my table after she said that she didn't have the money to pay for one of my books. In the years and months that followed, I figured that she wanted me to give her a book, and that's why she hung around my table for a few beats longer than necessary. The other one, in 2024, was this GORGEOUS young woman who worked the food service at the after party for that year's MoCCA Fest on the Saturday night before she came to my table on Sunday afternoon.
I remember feeling really alone, with no one to talk to at this after party, and this GORGEOUS young woman looking at me and smiling as she went around picking up empty plates and glasses from the tables. On Sunday afternoon she bought a book of mine I recommended to her, and SHE hung around my table, just me and her, for a few beats longer than necessary.
I've thought about that encounter, and how I just probably said to myself at the time, "What if I just let this opportunity slip through my fingers? What will happen then?" Well, slip through my fingers she did. I just told myself a few weeks ago, "Man, the idea of picking someone such as her up on the spot like that is WAY above my pay grade." Yeah, well, maybe it's time to ask for a raise. I may be ready to "process" more women I'm attracted to in a manner that actually involves making a bit of a try for them. Maybe or maybe not this particular waitress at this diner, but yeah, maybe some more than I'm used to making a try for on a more frequent basis than usual.