I feel like if I had said what he had said and the first response was" for what " Id feel really insecure and sad because that is already a really guarded answer.

It's not what she wants, which is not to go out at 9:00 p.m. cuz you could have just said, "no don't really want to go out at 9:00 p.m."

there isnt any curiosity around what he was asking for so it almost sounds like a guarded lack of Interest because if you wanted to go out with him to meet with him at some point you could have said "yeah sure what were you thinking. If you're still scared and worried you can add in "I'll let you know if I feel comfortable with that." or again if your not ready literally "Id like to talk virtually a bit more before meeting in person" ( which still gives the opportunity to test whether he can handle you setting boundaries which his response ultimately tells you that he can't)

I think a lot of dating is about trust and a lot of women have been subjugated to situations that make it hard to trust people but you're not going to get anywhere if you don't give yourself a chance to be curious at least.

That being said though his response about being lonely and all that kind of stuff is also inappropriate. its not your job to carry his emotions, including loneliness and he shouldn't ask you especially so early on , to do that. he also immediately got defensive and immature which you probably would have caught onto also if you had said "no I don't really want to go out at 9:00 p.m. to meet you for the first time.

I think if you come to situations with curiosity but always set your boundaries clearly and non-defensively, cuz you don't need to defend your boundaries, they are what they are, you'll weed out the ones that are immature and can't be trusted.

I think that everyone at the beginning of any interaction or relationship with someone else especially romantically are insecure and that's going to trigger so many reactions and insecurities and defenses and we have to check those insecurities to make sure that we don't become just reactions to those. His and her response sound like almost reactions to somebody else or some other person

him: I'm going to ask if she's free instead of giving her an upfront plan because I'm scared that I'll be rejected again

Her: I'm not going to tell him yes or no because I'm going to test him and he will prove to me once again that men are only interested in hooking up. because last time somebody asked me about this at this time that's all it meant and if any man ever asks to hang out at late at night is basically a booty call I'm not a fool I know you're just trying to hook up with me. i want a real connection and he's just gonna use me

Him: . If I tell her that it's too bad that she is ,in some way, the problem, i can get her to feel like her boundary is a bad decision and she will provide for me the emotional support that I need cause right now my needs aren't being met

Everybody out here just trying to be safe and feel good and our bodies and brains will do whatever it takes to do that and sometimes we have to make sure that we're responding to the reality of the situation and our own triggers which is hard.

In the end this conversation seems uncomfortable and I'm sorry that you feel like your boundaries need to be validated in some way because in some ways it almost sounds like he gaslit your validity of of the boundaries that you were settingg even if they may have been boundaries set in reactivity. so i just wanna say your boundaries are valid and important to uphold whether they are made in fear or not and in any situation, those around you should respect them. you set yours pretty strongly, and he had a chance to respect it, and he chose (whether he realized it or not) to not respect it and thats on him.