Tripp (Matthew McConaughey)is a thirty-something guy who refuses to move out of his parent's house and constantly brings girlfriends back to the house. Whenever Tripp feels a relationship is getting too serious, he lets the girl find out he still lives at home and she usually dumps him. After walking in on their son having sex with a woman again, his parents go to a friends bbq. All the other similarly aged people at the bbq admit to having adult children living at home also, except the hosts, who admit that their son Dougie moved out after finding "the right woman". At a furniture store, Tripp meets Paula, a beautiful woman and invites her to a lunch date. It turns out that Tripp's parents have hired Paula (Sarah Jessica Parker). She thinks that men still living at home lack self-esteem so she creates a relationship with the man, in order to build up his confidence. She pretends to like what the guy likes, she lets him help her through a crisis; she meets his friends & she lets him teach her something. All of this is designed to make the guy move out.