The ability to safely and trustfully talk to a partner is a real indicator that what is happening is for real. Even when the situation doesn't apply to ourselves, we apply the method of thinking that people are grouped into leagues. You are smart enough to know what this man's intentions and level of respect are. You will need to be able to meet him on equal footing for this to work, and getting to know him well enough that he doesn't feel "out of your league" is important. Yes, you need to go beyond the "he's out of my league" thing and also have more confidence in yourself, but those are separate issues from what I think is actually going on here. I do agree maybe you need to give yourself a little more credit just as a general rule. I feel comfortable with the person, really quickly. That doesn't mean it can't work, or that his interest isn't genuine! But it's just hard to say with this information here. If yes it's less red flaggy.
I can't answer any of your other questions, but you seem really down on yourself. If you're this uncomfortable now, I say trust your gut and move on. Could he be pursuing you for sport and he will lose interest once he wins you over or has sex with you? If this guy is going all-in for you--this guy who looks great on paper and seems to check off all the conventional boxes of potential good boyfriend, and presumably would know a good deal when he sees it--then you might just be undervaluing yourself. As a result he was very okay with paying for things, although I honestly and sincerely tried to hold my own- and now we usually go dutch. Either way, it's good to be wary of sliding, and to focus on commitment to things that are important to you, both inside and outside of romance. If he really is simply smitten with you and why not! But if you enjoy spending time with him and feel like yourself and feel like he's getting to know you for real, and vice-versa, it seems like not a bad thing at all. Two months ago, an interesting guy contacted me online. Your youth is quite attractive, by the way, especially if he wants kids, but This has nothing to do with whether you're totally desirable as you are or any accounting of "leagues," by the way. Does he really enjoy the "teaching and caretaking" role, or will he inevitably lose respect for me? There were genuine reasons why I was attracted to men that many women wouldn't consider conventionally attractive, but a small part of that was likely a need to control - with my looks, with their own acknowledgment that I was not someone they'd have considered pursuing because I'm out of their league. He requested that we stay in touch as friends and keep going to things together and "maybe you'll change your mind. I haven't done this yet but I am dating someone new and looking forward to this getting to know you tool. I am saying this not just as a stripper where this behavior is rampant; as a uni student and in the normal world workforce, men who are pushy about not allowing you to break up with them and shower the objects of their romantic interest with expensive, obligation-making gifts are controlling and bad news. Pretend he is simply from another culture and grew up speaking a different language from you. We need to stop forming silly little leagues based on the shape of someone's cheekbones. It's almost like he made up his mind about us before he even met me. But the point is that one thing is true for all of us: And to his friends. If you're thinking this right now, then you're still in the mindset of League Theory. Yes, you need to go beyond the "he's out of my league" thing and also have more confidence in yourself, but those are separate issues from what I think is actually going on here. Basically, if you are a 10, you should be willing to settle for another 8 or so. Also, his ability to afford these clothes speaks to the fact that he may have a ton of money, which is another sign that he could be out of your league. I was kind of a late bloomer and didn't even kiss a guy until I was It may be that he's less in love with the real you and more in love with the version of you he expects you to be.
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