Okay I'm just going to describe the scenes I remember because it's been a long time.
Mother character gets asked what happened to her son's father, she describes an encounter where she was working at an Army hospital (WWII?) and encountered a dying pilot. She says she wanted a child but never wanted a husband because she was afraid, he would weigh her down. She says she seized the opportunity to get exactly what she wanted and had sex with him. I distinctly remember the character she told this to saying "You raped a dying man?" with a sense of disgust and horror.
There are scenes where the son asks his mother about who his father was and she says that he isn't important. He called his father a "flyer" and drew a picture of what he thought he looked like with crayon.
Then sometime later (like 20-30 years) he is an adult with a wife and children of his own. I don't remember if gap in that time was covered or if it was just an immediate jump.
Him and his wife are in an unhappy marriage, and he contemplates cheating on her with his kid's babysitter as he's driving her back home. That was the last thing I saw.
Thinking back, it had more of a TV movie look to it than a theatrical release. It also could have been a TV show with long episodes, but I don't know.
Thank you so much for your help!