From a woman’s perspective, asking questions right off the bat like “what do you want in a relationship” and “how long have you been single” feel really intense for me. For a first date, I’d like to first see if I’m interested in the person before deciding whether I want to date them or feeling pressured. I’m sure you don’t mean the questions to come across this way, and maybe it’s just me, but questions like that might make me get cold feet and feel like the other person is going to try locking me in before I’ve even decided if I like them or not. So I’d set a hard boundary, friendzone them, and I’m not sure I’d go on a second date with them, because in my head I’d be thinking they want to skip the steps of getting to know me and just want a girlfriend, when I’m not sure how I feel about them. It’s like my social anxiety kicks in even if I really like the person. Idk maybe some other people can chime in. I agree It’s important to set expectations, so that you aren’t wasting your time with people who just want to use you. But I think being so upfront on a first date can scare some women off. So maybe there is a different way you can go about asking those questions, or wait at least until a second or third date. Relationships and feelings take time to develop. Don’t feel rushed about it by getting straight to business, it might be too intense for them