In the story of "The Best Girlfriend You Never Had," analyze Lucy's relationship with her father, mother, and Leo in detail to find evidence that their relationships are not healthy.

Lucy's relationship with Leo is not healthy. Though they spend time together and read poetry to each other, Leo is not in love with Lucy but with a woman called Guenevere, but Guenevere does not seem to know that Leo exists and forgets him after meeting him. However, Leo says that Guenevere's dismissive behavior "adds to what he calls her charming basket of imperfections." He only likes women who don't like him back, making his relationship with Lucy strange and unfulfilling. 
Lucy's relationships with her parents, who are alcoholics, is troubled. She says that she and Leo used to eat dinner "on TV trays next to our parents and their third martinis, watching What’s My Line and To Tell the Truth on television and talking about anything on earth except what was wrong." Lucy's family life is filled with a lot of drinking and not a lot of love or honesty. Her favorite childhood memory is when she pulled a heavy urn on top of herself when she was four and crushed both of her femurs. She recalls her stay in the hospital:

"My parents, when they came to visit, were always happy to see me and usually sober. I spent the remaining years of my childhood fantasizing about illnesses and accidents that I hoped would send me to the hospital again."

The only time her parents paid attention to her was the time she was in the hospital as a little girl, and she sadly prayed while growing up to have another accident so her parents would focus on her and love her. Her parents did not provide her with a lot of acceptance or love, and when she asked her father if he approved of Jeffrey, one of her boyfriends she hoped her parents would like, her father said, “Lucille...I haven’t ever liked any of your boyfriends, and I don’t expect I ever will. So why don’t you save us both the embarrassment, and not ask again.” Her parents rarely gave her the affection and attention she craved, as they were involved mainly with drinking.