A lonely, neurotic, and hilariously honest middle-aged man reunites with his estranged wife, and meets his teenage daughter for the first time.
Harrelson stars as Wilson, a lonely, neurotic and hilariously honest middle-aged misanthrope who reunites with his estranged wife (Laura Dern) and gets a shot at happiness when he learns he has a teenage daughter (Isabella Amara) he has never met. In his uniquely outrageous and slightly twisted way, he sets out to connect with her.—Fox Searchlight Pictures
Wilson (Woody Harrelson) is a lonely and neurotic middle-aged man living in Minnesota with his dog and sole companion, Pepper. He has spent the last seventeen years divorced from Pippi, who aborted their child and turned to a life of prostitution and drug use. Wilson has given up on his dreams and aspirations.Wilson's life turns for the worse when his friend Robert (Brett Gelman) moves away along with his family. Robert moves to St. Louis, Missouri, with his wife Jodie (Mary Lynn Rajskub) so they can afford to buy a house. It is clear that Jodie does not like Wilson, and she forced Robert to move so they could get away from him.
Wilson lives alone in a tiny apartment, has next to no friends and is a socially awkward person. Wilson believes that the humans have lost the sense of community and camaraderie with their friends and neighbors.He will strike uncomfortable conversations with complete strangers about the stage four lung cancer of his own father.
Wilson has to travel to meet his father who has been diagnosed with terminal cancer. He leaves Pepper with dog sitter Shelly. At the hospital, Wilson wants his father to display some emotion of love or hate, but he dies instead.
Wilson takes care of the funeral arrangements and the last possessions of his father. He meets his old school friend Orson (David Warshofsky), as he is the only living person who shares any memories with Wilson. But Orson is a jerk, and Wilson decides not to be friends with him. Orson says that his father is still alive and refuses to die and seems happy that Wilson is rid of his own father. Wilson says that he wants to start dating again, but Orson says that he gave up on women a long time ago. Wilson calls Orson a toxic, soul-sucking Vampire.Wilson drives his father's car back to Minnesota.
Desperate to meet someone new, he tries unsuccessfully to court a woman at a pet store by conversing with her and rear-ending her vehicle. The woman runs away in haste as a little girl points out that Wilson rear-ended her on purpose.
Wilson goes on a date with a lady named Alta (Margo Martindale) he meets at the supermarket and talks about is ex-wife who left him 17 years ago & had an abortion. Alta is into internet applications and suggests that Wilson do a People Finder search to locate his ex-wife.Alta tracks down Pipi's sister Polly. From there Wilson calls Polly and finds that Pippi relocated back to the LA recently. Wilson tries to track Pippi (Laura Dern) down in LA by asking the local prostitutes. Finally, Wilson meets Pippi who is a waitress at a middle-class restaurant.
They initially have a tense reunion as she has been rebuilding her life (and she did want the restaurant to know that she was a prostitute and had a substance abuse problem in the past), but they warm up again and spend the night together. Pippi reveals to Wilson that she didn't abort their child, a daughter, but gave her up for adoption.
Through the adoption agency, Wilson tracks his daughter and Pippi and Wilson ambush her in a mall, when she is being harassed by her school buddies for being a "fat person". Pippi, Wilson and Claire (Isabella Amara) connect and start spending time together. Claire was adopted by a really rich family, who don't spend too much time with her.Claire doesn't want to introduce Pippi and Wilson to her adoptive parents.
Pippi hates her sister Polly (Cheryl Hines) and decides to show off Wilson and Claire to her as "her family" by spending a weekend with Polly's family in the suburbs. Wilson tries to make it work, but the trip looks like something out of a horror movie.Polly finds out that Claire has lied to her real parents to be with Wilson and Pippi. Polly and Pippi have a horrendous fight and Polly gets them arrested for kidnapping. Wilson is jailed for 36 months and Pippi walks when she makes a deal with the state to sell Wilson out.
Wilson's awkward social tendencies and his tendency to shoot his mouth off, get him into trouble often inside prison, with him being beaten by fellow inmates. But slowly Wilson wins them over with his innocence. After 2.5 years Pippi visits Wilson in jail only to tell him that she is moving to Australia with her AA sponsor, Tyler.
Wilson is released from prison, and he returns to his hometown only to find that all his know hangout spots have closed. He returns to his pet sitter Shelly (Judy Greer) only to find that his dog Pepper has died in the 3 years he has been behind bars. Wilson is devastated, but eventually starts dating and then having sex with his dog sitter.
Claire reaches out to Wilson. Wilson demands an apology from her for ratting him out to the feds. Claire tells him that she is pregnant. Wilson is ecstatic once again. But the Claire's adoptive parents Cassidy don't want Wilson to have to do anything with Claire and push him off.Eventually Claire agrees to make Wilson a part of the baby's life and he lives happily with the dog sitter (and a new dog).
