Okay, so my parents' friends have a daughter that I feel like I get along with really well, and would love to start something with her. My parents also like her a lot since she does really well in school and has a good relationship with her parents. Now, I've never expressed my interest with her because I don't want to piss off her parents. Anyway, the other thing is the age difference. I'm 23 and she's 17. I've known her for quite a few years and always felt like I got along with her but never made a move because I wanted to wait until the age difference between us became less significant. Also, her dad is really protective of her, so don't want to piss him off. And of course, I'm concerned that if things go wrong between us, that it'll ruin the relationship between my parents and her parents. The last thing is that if she isn't interested in me, I fear that it'll make the relationship between me and her (and hence my parents and her parents) complicated. I have a healthy friendship with her but never brought up a relationship at all. Since my mom likes her, she really wants me to hook up with her. However, I'm afraid that doing so would cause other problems. Any thoughts?