For what it's worth, here's a point of view from the flip side: I'm a 44 year old female and have a very strong and natural friendship connection with a 19 year old male that I met through family. The age gap doesn't bother him, but because the gap is so vast, I feel like I'm doing something wrong, and that I shouldn't share deep emotional thoughts with him, because people might think I'm trying to manipulate him in some way. I'm worrying so much about it that I keep on backing away from conversation and he's starting to notice that I'm avoiding him. It's such a hard situation to be in, because our friendship enriches my everyday life, yet I feel pressure from the general rule of society that suggests, if an older woman is close friends with such a young male, then she must have impure motives. I understand that not everyone has decent intentions in these types of situations, and yes, of course that should be looked down upon, but that is definitely not the case with me. I just want to be able to enjoy the emotional and intellectual connection we have without feeling like I'm doing wrong by him.