Date was really nice but mentioned quite a bit how broke he was

I don't have much dating experience so bare with me here.....He was so cute, so nice, and had a lot of interesting hobbies. He paid for my coffee which I thought was sweet. But about a minute into the date he said he was broke. And then he kept sprinkling it into conversation the whole time and it really bothered me. Now I have no problem going out with someone who doesn't have the best financial situation and has aspirations for something better but the mentioning of it quite a bit was kind of weird on a first date. Is this strange or am I overthinking it? I'm gonna go out with him again but I'm a little weary. I've been in some previously bad situations with guys trying to make me their step in mothers and I tend to brush past the red flags in that same regard so I'm cautious with this sort of thing. What do you guys think?