Hey man, thank you for your advice. I can see why some people are saying you're generalising, but your comment did make me think about my sexual confidence (or lack thereof).

She's the kind of person who has mostly been with people (men and women alike) who seem to primarily be sexually dominant. I usually pride myself on being confident and forward when it came to men, but it's easy to be that way when men make it pretty clear whether they're into you or not (another generalisation of course, but I've found that guys who are attracted to me treat me completely differently from guys who aren't). Plus, if I come onto a random guy, I don't really feel like I have a lot to lose if he doesn't end up feeling it. We can just move on and go on our merry ways.

In this situation, I feel like I do have a lot to lose if things end up being awkward or something due to miscommunication. I feel like a lot of her sexual relationships turned sour because of ambiguities, uncertainties and either her not making her needs clear, or the other person being totally tone-deaf to what she wants. While she seems to like for people to just "go for it", in the long term it seems to always end badly and I don't know if I want to make that mistake as well.