I actually did this yesterday (in spite of what I wrote above!)—it's not FR-worthy as I didn't push things as far as I could have, but I'll post about it here. I personally go for thin, tall, willowy younger ladies as a general preference, but this one surprised me a little. The story is anticlimactic though since I was not prepared to put in the effort required on a Tuesday night of all days, for the uncertain payoff.
I went out around 10 PM in search of
business visitors at hotels, which turned out to be fruitless. Two hotel bars I checked were completely dead (and obviously not much else happens Tuesday night). At the Loews, there was a group of maybe a dozen young women in their late twenties sitting together, which looked promising, but I couldn't immediately see an individual I'd want to approach without blatantly taking time to scan faces, which would be socially clueless. So I briskly opened the group with a "Hey ladies, how's your night going?" to assess reactions. I got a few giggles and heads turned my way, obviously, but none appeared particularly attractive.
Less than a minute into the conversation, one of the least appealing girls made an unwelcoming remark, presumably in the spiteful knowledge that she'd not be the one I'd choose to interact with in any case. I gave her the
"Okaaaaay..." Look and ejected.
Side note: for some reason the Loews seems to host big groups of females regularly; I need to investigate this. One lunchtime I even saw mini-groups emerging from a conference, all identically tagged, consisting of very young (18-19), reasonably cute girls accompanied, bizarrely, by overweight, astonishingly low-value youths (seriously, just one notch above social retardation: clues were unmissable in their clothing, grooming and written across their faces). I couldn't find a way to get around these guys to open the women, but it was eerie: I cannot imagine what sort of an event brought together such an unlikely matching.
Back to the main narrative; after failing to find anything of interest in the hotel bars, I had decided to head back to the car and was almost there when at around 11:15 PM I saw in the street an atypical grouping of three women and one man. On account of the man I passed and ignored them, but right after I got ahead, he left... he was a bum pestering them for change. I hadn't bothered to take much of a look at these girls, but for the sake of experience I slowed my pace and opened over my shoulder exactly as before: "Hey ladies, how's your night going?"
Then I took my first proper look; two were African-American, which is not to my taste, while the other had long blond hair but could lose a few pounds. Nonetheless, she quickened her pace a little to draw alongside me while the others dropped back, so I addressed her: "You have very pretty long blond hair, what's your name?"
We got into conversation and I realized that she was actually cute. In terms of facial features, she was very much my type. She told me she was 28. If she lost maybe fifty pounds, she wouldn't just be cute, she'd be
hot. I know how hard it is to lose fifty pounds though... I've done it.
They were heading for a bar and agreed that I could come along too. After some ado with drinks etc. at the bar, we took seats at a table. The table had two loveseats, one opposite the other on each side. Maximum occupancy of each was probably three, so I took one with PrettyPlumpBlonde and her friends actually moved to the one opposite to let us be together.
She was very receptive to deep-diving, gave me a sip of her drink, maintained constant eye-contact, didn't flinch when I moved so close our legs were touching the full length and had my arm around her, and appeared to enjoy it immensely when I got my face up close (ostensibly on account of loud music) to murmur in her ear. This was all within ten minutes of us being seated.
I didn't do enough to put the other two at ease though. Once I was practically wrapped around PrettyPlumpBlonde, I glanced across the table and saw two pairs of unfriendly ebony eyes, the depths of equatorial Africa staring out at me through them. The lower-status one just stared, but the other was clearly the alpha female of the three and actually motioned (nonverbally) for me to back off.
I barely adjusted my position but she seemed to accept this. This was clearly an "envious" cockblock, in spite of her explaining that they were "very protective". I started to challenge and the alpha complained "We don't know you... you barely acknowledged us outside". (Lesson for the future.) Then I remembered not to break circle and I turned all attention back to PrettyPlumpBlonde, saying: "Your friends are telling me to back off. Do
you want me to back off?"
She replied "No, you're good" and remained snuggled close. I asked her to tell them herself, and she told them it was okay. We continued like this for a bit. I found myself getting quite aroused... she had a surprising amount of sex appeal.
I think though that the damage had been done, because she broke circle to get another drink and when she returned the alpha female engaged her in conversation which essentially shut me out. I cooled my heels for a few minutes, but when it became apparent that I would need to put in a lot of investment to get her warmed up again, I decided to call it a night. I had a full working day the next day and our logistics were less than perfect. If she'd been fifty pounds lighter, though, I'm certain I'd have stayed as long as it took.
I didn't bother with a phone number, as I figured it was a now-or-never deal, but on reflection, perhaps I should have given myself that option. It would have been easy to justify not closing, on the grounds that I wanted to give her a chance to enjoy a last drink with her friends (she's leaving shortly for the West Coast) and we could chat another time. If she's worth opening, it's worth cultivating her interest while it lasts, until you actually get the lay. After that, it's up for debate. Another lesson for me!