I am good friends with this couple who are about 30 years older than me, and have recently begun to develope feeling for their daughter who is around my age. While I am friends with her already I am closer to her parents and think that our friendship could be at risk if I started dating their daughter. My first thought is to ask them if it's ok, but even that seems risky.
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From my experience, it all comes down to whether or not you can impress the parent or brother.
Have a friend from high school and one summer I developed a thing for his sister. Because we were such good buds, he was all for it.
Had a mother from work who found me all sorts attractive so she insisted one day that we walk her dogs together along with her daughter whom I should meet.
My point is that it's doable.0