Older woman #3 was a bartender at a small bar / lounge in Barcelona, which draws a crowd of 18 - 25 year-olds. * I believe that when an older woman is surrounded by pretty young things all day, she develops a sense of humility and vulnerability that her peers do not. Female high-school teachers might be this way too. In any case, I noticed her staring back at me several times one night, but since she was easily a 9, I figured she was just gaming me for a larger tip or something.
But when she had a lull in customers, she walked over and started chatting with me. Over the next hour or so, she was leaning in, grazing her cheek against mine to speak, reaching out to touch my arms, and laid her hands on top of mine. It never seemed eager or calculated, like a cougar would do, although her movements were more relaxed than those of a youngster.
I never mentioned her looks, starting off instead by asking if it's hard being a bartender since everyone must treat you like a robot -- she chuckled yes -- and proceeded to ask her what she does for fun, what she would like to do, etc. She was a painter, originally from either Mallorca or Menorca, so I mentioned that I was also a foreigner, and started talking about how guys don't do artistic things for the girls they love anymore. (I used to write them poems, a bad habit that I ended around this time.) Looking back, it was a very cheesy thing to say, but she responded really well to that remark, probably just because she was an artist (or thought I was cute enough to forgive).
Near the end of the conversation, she asked how old I was, and I said 23 (though I was nearly 24). "Oh my, you're very young, aren't you?" she said in Spanish. Shit. I asked her the same, and after a pause, she confessed that she was 28. I didn't know at the time that I was supposed to playfully tease her about being too old for me to talk to, so her anxiety about the age difference only grew from that point on.
When I returned the next week, she ignored me the entire time. Still being rather clueless about girl behavior, I waited around at the bar until a male bartender approached me and, in the friendliest way possible, told me that I was making her nervous. So a five-year age gap was all it took to go from heavy flirting to the cold shoulder, eh?
I didn't bother talking to older women after this, although by then they'd pretty much lost their looks anyway. This one simply flew under my radar: she had the same ultra-petite body type as older women #1 and #2 and showed no signs of aging -- I thought she was 20 or 21. That's probably how she got such a difficult job.
It's not cheating to include someone I thought was several years younger than me, for the simple reason that she didn't act that way, only looked it. Like older woman #1, who was almost the same age, her level of Neuroticism had settled in a more mellow range. That did make her appear less girly and high-energy, but I admit that there is a certain attractiveness to a mellow personality when the girl is strikingly gorgeous, like a mature cat who is happy to flop on your lap and purr for hours on end, and unlike a kitten that's too occupied in bouncing itself off the furniture and wanting you to constantly run around with some string for it to chase.
* By the way, there are lots of these places in Spain, including the gigantic club Razzmatazz that attracts people from hours away every weekend. In the US, there are only a handful of 18+ clubs, although these repel 22 to 25 year-olds (who think they're too cool for college-aged kids), and 21+ clubs, which in practice cater mostly to the wealthier 30-something group. The typical option for college-aged kids here is an awful frat party, and out-of-college kids have almost no places that cater primarily to them.