
Seriously though, i feel like the idea of a one-off encounter, like a one night stand, is very romanticized in the media. I can't say with impunity, but I don't think it is quite as casual or overwhelmingly frequent as it seems.
If this situation is something you really want, I totally respect your goals and hope you the best developing further toward reaching it. However, I don't think it's healthy to see an idealized, emotionally unattached, one-night-stand sort of encounter as something every Joe on the street can easily take part in. That seems like you're just discounting yourself and your abilities.
If it helped to be more 'playful' in a situation, even sexual, I say go for it.
You seem very earnest and I appreciate that. Don't discount yourself in lieu of society's standards of emotional and physical contentment!