Concerning the Zoe story mentioned above, I think it's worth mentioning that that developed over a fairly long period of time if I remember correctly (a few years?). The full thing is somewhere in this mess of a forum and it's definitely worth reading if you have the time. Mostly, the two of them were really cool for a while.
That's quite true. However, the length of time you've known someone isn't really a factor; sussing our their attitude toward the subject is. A fair number of folks know I run a foot fetish video business, and they either don't care or think it's interesting. I've had a couple of women that I'd only just met (or only knew on a superficial level) express an interest in modeling, even though not all of them panned out for one reason or another.
For example, I was at a party thrown by a friend of mine, and was chatting with "Sandy", the wife of another partygoer who I basically only saw when she showed up to these things. We were friendly, though, and as the first time she spoke to me she made a dirty joke, I knew that she wouldn't flip out if she knew about the foot thing. So when conversation naturally wandered around to what I did last weekend, I said I had a photoshoot with a model for one of my side-businesses. She asked what kind of side-business, so I said "foot fetish clips" - and left it up to her to either pursue the topic or drop it. She pursued it, and eventually said that she might like to try that sometime, pointedly showing off her foot. I nodded, said, "Absolutely, I'd love to shoot you", and handed her my card. (ProTip: Have professional-looking business cards.)
I was about to change the subject when another woman overheard me say "I'd love to shoot you" and said, "Wait, what? You want to SHOOT her?" - I laughed and said "with a camera!", and then the other woman commented about how she'd love to get into BBW modeling, maybe even fetish, but she didn't know how. I gave her some people to contact, and also gave her my card.
Now, granted neither Sandy nor this other woman actually followed up to schedule a shoot, but the point is, I did ask, at least one of them was a casual acquaintance, and it wasn't creepy or off-putting. You have to know how to gauge a situation to see if the topic would be welcome, regardless of who you're talking to.
