Need help figuring out some stuff with a girl

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So, in short, I ended up having a fling for this girl last summer for about a month before she eventually ended it and then left for university

I saw her via mutual friends a few weeks ago and then she asked me to hang out yesterday, and we spent a few hours talking and catching up. She's been through a lot of shit (slept around with some guys, had her heart broken, was sexually assaulted), and I'm not sure if it's her usual habit of slightly oversharing or if she needed someone to talk to. I think it might be both

But for some reason it kept me up all night. I think it's because we're in different places in life. She's discovering her sexuality while I'm staying at home after dropping out and I of course have had only one experience in the past year, with her (I was over her after about a month though, when we broke up).

I like her a lot still though. I have no idea how she feels about me, because she never really gave any clear signals during our last hangout. I enjoy just spending time with her, and I'm thinking of asking her out. But given her past experiences, and the fact that she seems more into hooking up with people, I don't know how to broach the subject.

I'm caught between straight up asking her out, or telling her my feelings. Is it dumb to just ask if she likes me?

If she rejected me, I'd still hangout with her to be honest; I enjoy being around her. But then I dont' know if I'm being a massive cuck or what.

Any advice on how I should handle this? I know I'm overthinking, but I'm not exactly keen on making a fool of myself by going about it the wrong way