chemistry w/ chicks?

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Hi /adv/ , if I don't feel chemistry with a girl right off the bat, should I discontinue seeing her?

So I've seen this other chick about 5 times now, and as much as she's incredibly hot, we don't really seem to have that "chemistry". She's pretty timid because she has an over protective mother (she's 16), and I don't exactly feel enthusiastic to meet up with her again. I'm going to see her again this Sunday. If I don't feel that spark, should I just drop her? Will chemistry come anytime soon?

On the other hand, I met up with a girl I barely knew in high school last night, and we hung out from like 8 PM - 1 AM and it was lots of fun. We had some drinks at the park, went to an arcade, we had really good conversation flow, in general she was lots of fun to be around. Although, apparently she fell into a depression a few months ago and for the most part has no hobbies or interests rn. She also used to have a thing for a close friend of mine about a year ago. They went to prom together, and they were drunk at an after party and the only thing he remembers is fingering her. So he doesn't remember if he fucked her. Also I'm not sure if she still has a thing for my friend.

To sum up all of my questions.

1. Should I drop girl with no chemistry? (desu everything feels kind of forced, even the flirting. cringe.)

2. Is girl w/ depression red flag?

3. Am I cuck if I want to continue seeing this girl because of the possibility of her having fucked and still having a thing for my close friend?