Very upsetting. What I found so curious about it was how remarkably unaware and juvenile Simon's friends were. When boys are in their teens, they might brag about and encourage sexual activity but you are supposed to grow out of that. They didn't.
And Simon did have young women interested in him, those friend-zone girls, but rather than respect that and let something develop, they would seduce them away from Simon rather than let things develop naturally. When I was in my late teens/early twenties (high school and college) there was an unwritten rule that you don't do that.
They couldn't figure why nothing developed with Simon and those young women when they were making it impossible.
Simon's real problem wasn't with women; it was his friends.