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It's definitely inappropriate. Unless you've been involved or have shown interested in being involved with him, then it's totally not cool for him to talk like that.
I've known guys like that. After I've had enough of saying "stop that", then I just cut them out.
I once had a guy, who I was friends with for years.... we'd lost touch (because I was always annoyed at him being inappropriate). I reconnected with him like four years later... and within two conversation he'd ALREADY restarted behaving the same. So I cut him back out pretty quickly.
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"The time has come, the Walrus said, to talk of many things. Of shoes, of ships, of sealing wax, of cabbages, of kings! Of why the sea is boiling hot, of whether pigs have wings..."
"I have a problem with low self-esteem. Which is really ridiculous when you consider how amazing I am.
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