What we do know is that he is really, really good at dating. So on the one hand, if you went in there and had sex with virtually no connection established other than some playful, sexy banter and verbal foreplay, that will work against you in terms of being evaluated as a relationship partner. Not just sex, but really aggressive, dirty sex and sexual role-playing. That means you're more likely to misread them, and it also often means they'll feel less comfortable voicing their displeasure. Often, women in this situation will have to mentally calculate: And the other unfortunate reality is that lots of the perpetrators don't necessarily realize they've done anything wrong — because there wasn't some violent struggle; the other person just didn't seem very into it. Is sex on the first date a relationship killer? Given the set-up you described, making a relationship happen here might be tricky. I'm not saying you can't have hot, consensual sex on a first date. His first text message was sexual and, being a flirty person, I responded back with some flirtatious banter. Not every guy will go for this he might not be in that place , but if he is, he might just begin walking down that path with you. At least, it would at the very least not hurt you and might even help chances for a relationship. Unfortunately, our culture has this vision of the rapist or the sexual assaulter as being some masked creep hiding in the bushes. By then, you might actually know each other well enough to discuss what does and doesn't work in the bedroom for you — and the anticipation you've built up will make the sex that much hotter. A sweet, caring side. Again, on a first date, you don't know this person very well. Well, that "not very into it" should be a big, flashing red light to you.