<human>: So my mom and dad have a circle of friends and one other husband and wife couple have a daughter and a son. me and the son always chat at gatherings and share the same interests. 

I kinda like him and would like to fool around with him but there are some obstacles. One is that based on what he has told me, he has never had a girlfriend and I can assume he is a virgin by his personality. I just want to fool around and worried that he'd get way more attached than me and it will end badly.

Another thing is the cultural stuff. Me and him are both from a sexually repressed culture and I am not sure how to go about making a move since I don't know how it will be dealt with like for example it may be seen negatively if a woman asks you out but I am not sure) since we are pretty much westernized it shouldn't but I still worry

I also worry about the parents and their friends finding out, Unfortunately, they tend to gossip and I'm not sure how'd they re-act, His sister is dating a different guy from our group and they are practically engaged and no one seems to mind which is good.

am I just sweating the small stuff too much?

Can you condense the text into three sentences or less?
<bot>: I like a guy from a group of family but scared that personal/cultural/social problems will get in the way if I try and make a move on him and this is making me frustrated