I believe that you are overthinking the entire issue and he is only making small talk with one of his customers.
Also, it would be very unprofessional of him to try to pick up a customer as this is most probably against the rules of the company he works for, provided the company is a serious one.
The fact that you call him "freaking hot" leads me to believe that you are probably not the only one of his female customers to share that kind of opinion. If he is just a little clever as he is "hot", then he should know that flirting with customers is a taboo topic.
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He's trying to get a female perspective on what's going on in his romantic relationship. Sounds like he doesn't feel ready for what his partner is ready for and is wondering if all women her age (ish) feel that way.
Your mental health doesn't define you. If he finds out about that he will only learn about your past, that's not a bad thing, it's the history of you.
We all have some degree of mental health problems... Some more, and some less. It's what you do with then what matters, and he will see that you were taking care of them. If you ask ne, that's nothing but a good thing.
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sounds like just making convo
I'd keep it casual until you're more certain.
let it go
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