She told him why didn't you ever ask me out? He was puzzled and never knew that was an option. He didn't consider it since the guys she dated was nothing like him.
He didn't cross that boundary line. He didn't date close friends or within his circle of peers. He didn't date friends family members or exes of people he hung out with.
This would anger them and they would distance themselves. Mad holding a grudge if the friendship failed how could it be a relationship. He had a hard time opening up since his feelings would be used against him. Staying single because his emotions would get the best of him. Dating was fun at the beginning it was easier to get physical than get to know a person.