The chemistry between any 2 guys is gonna be unique, so that fixed "textbook" answers with a simple "yes" or "no" will always be difficult, and suspect. At best there can be general guidance.
I remember cruising a guy I hadn't seen before in a gay club, who really intrigued me, and we hit it off, but I could see he didn't want to leave with me. So I put him on the "back burner" in my mind but didn't totally forget him, either. Nor did I try to contact him, though through the club owner whom I knew I might have gotten that info, which I later learned he had.
But my patience paid off, and sure enough, 2 months later I saw him again, and this time I really went after him. But so did some other guy, and before I knew it the 2 of them had left together. I've never had that happen to me before or since, and I felt like a total loser & fool. But I have persistence if nothing else (and stubbornness), and I wasn't done with him yet.
The very next night he was there alone again, and this time I let out all the stops, refusing to go 3 strikes in a row. By now I figured I had nothing to lose, so I guarded him like in a basketball game (mixing my sports metaphors here), not letting him get within 5 feet of another guy, and bluntly asked him as closing time approached if he wanted to go home to my place. He accepted, and from that moment we dated for 2 years, and remain friends to this day. Unfortunately for me at the time he's a guy who prefers to remain single, as he does to this day, and that's why I eventually moved on, because my long-term goal was a monogamous partnership, that I now have.
Moral: patience, timing, and reading the other guy correctly. I can't help you read this guy you've met, you're gonna have to use your own judgment & instincts. Whether he'll be flattered by attention, or turned-off by pestering, I can't guess. But isn't falling for a guy a great experience? If this guy doesn't pan out I'm sure you'll have others.
(And BTW, I know your city very well, even led the Pride Parade down Hennepin on my motorcycle, had plenty of my own gay escapades right there, including with the guy in the story above, a good place for it.