We begin with a flashback of Maggie and Milo as children dressing up for Halloween with their dad. Maggie tells us that maybe they got their problems from their dad. Everyone referred to her and Milo as the Gruesome Twosome.
In the present, Milo (Bill Hader) is blasting music in his apartment. He draws a face on his bathroom mirror, then lays in the tub. Off camera he slits his wrists. The water in the tub gets bloody.
Maggie (Kristin Wiig) is at home in her bathroom holding a handful of pills. Her phone rings. Her ring tone is the Growing Pains theme song “As Long as We Got Each Other.”
Maggie goes to the hospital and visits her brother. It’s been ten years since they’ve seen each other. A nurse gives her his suicide note. It read, “To whom it may concern. See ya later”. She suggests he go back to New York with her. He resists because he thinks she’s only making the offer out of guilt, plus he has fat goldfish to take care of. She says he can get new goldfish.
The go to New York and Milo meets Maggie’s husband Lance (Luke Wilson). He’s an odd match for Maggie, but is clearly a super nice guy. He brags about how Maggie is always trying new things. Currently she’s taking scuba lessons for when they have a late honeymoon in Hawaii.
The next day, Milo bums around town and finds Rich (Ty Burrell) inside a bookstore. He watches from a distance. Later he goes to a gay bar, but it’s “dyke night”. He goes home to Maggie’s house drunk and wakes her and Lance up by bursting into their bedroom and telling them about his adventures with the lesbians.
The next morning Milo apologizes. Maggie suggests he do some work clearing paths in the woods with Lance.
Maggie goes to her scuba lesson. She and the instructor Billy (Boyd Holbrook) clearly have a bit of sexual tension. When she goes home, she finds that Milo has invited their mom (Joanna Gleason) over. Their mom is a bit of a free spirit and missed Maggie’s wedding because she was on an “insight retreat”. In fact, that’s why she’s in New York. She’s at another insight retreat at Woodstock. She invites everyone to visit her at any time. Maggie calls her bluff and we see that their mom is all talk and really has very little interest in spending time with her family. She has a new family with new children now. Maggie secretly takes birth control pills. Maggie says to Milo, “Can you imagine being married to her? I’d jump off a bridge too.”
The next day Milo works up the courage to speak with Rich. He brings a copy of Moby Dick to the counter. Rich is surprised, but relieved to see that Milo has no animosity towards him. He tells him that he read Moby Dick a long time ago when it was given to him by a good teacher.
Maggie ends up at the bar with Billy the scuba instructor. She seems uncomfortable and wants to leave, but instead they end up having sex in the bathroom.
The next day, Milo is taking Maggie to work. She asks if he thinks she’d make a good mom. He says that she’d be overprotective and uptight. She gets angry and leaves. Milo tells Lance about the conversation. Lance says, “Sometimes it’s like landmines, man.” He finds himself stepping on them all the time and he’s figured out that all he should do is apologize and they can move on. Milo goes to pick up Maggie from her job at the dentist office and apologizes. He says she’d make a great mom and he jokes that his real problem is her morbid obesity. She cleans his teeth and they both get high on the nitrous.
Milo shares the fact that he ate pussy awhile ago because the girl looked like a young Debbie Harry. He didn’t like it. He tells Maggie she has to share a secret. She confesses that she’s been taking birth control pills. It’s only partially because she doesn’t want to have kids. It’s mostly because she’s been sleeping with the instructors of every new venture she’s been taking. Billy is just the latest one. She says that Lance is too good of a man to be married to a whore. Milo says she isn’t a whore. She’s a restless housewife with whore like tendencies. Milo is late for a meeting. He says he has to meet with Kevin Clancy.
Instead, Milo goes out for drinks with Rich. Rich asks if Milo remembers a little copper whale he gave him a long time ago. Milo not only remembers it, he carries it with him everywhere.
Maggie is at home watching Deadliest Catch with Luke. She tells him that she loves him.
Rich and Milo are in a car and Rich apologizes for what they did a long time ago. He’s dating a woman now and has a son. His son doesn’t know about Milo. They end up spending the night together. Milo lies and says that he’s doing much better in Los Angeles than is what the reality is. The reality is that he’s a waiter at a tourist restaurant. He tells Rich that he just got an agent and is busy as an actor. Rich asks if Milo would give his agent a screenplay he wrote.
Maggie tells Billy what they did the other night was a mistake. They bang again. She goes home and violently carves a pumpkin. Milo sees she’s upset and cheers her up by forcing her to lip sync along to “Nothing’s Gonna Stop Us Now.”
Milo is finally getting the swing of his job. He goes to Rich’s place and ends up meeting Rich’s son. Rich is furious, so Milo goes out and gets super drunk. He finds himself on a rooftop, drunkenly staggering along the edge. He drops the little copper whale over the side. A cop finds him and takes him home.
Milo tells Maggie that when he was a kid there was a bully named Justin Meyer. Their dad told him that Justin was the kind of kid who would peak in high school. Milo imagined going to a reunion and Justin would be fat and bald while Milo would be a famous actor with a wonderful boyfriend. He looked up Justin online. Justin has a nice job, nice wife and a couple of kids. Milo realized that Justin didn’t peak in high school. He did. Maggie tries to comfort him by telling him that no one is a famous actor. Milo says that George Clooney is. Maggie tells him that she needs to know that he won’t check out on her. He promises to do his best. He later reads Rich’s script. It’s a romantic comedy for someone like Jennifer Aniston in mind. He’s not impressed.
Lance is out doing Fantasy Football, so Maggie and Milo get dressed up for Halloween like they did as kids. They do a Cemetery Walk, a thing they haven’t done since their dad died. They talk about the weird child psychologists they had as kids and show each other their skeleton tattoos. Then they dance. Milo goes to the bathroom and leaves his phone behind. Maggie sees that Rich calls. She calls Milo on this and points out that Kevin Clancy moved away years ago. Rich was a teacher who molested Milo when Milo was 15 years old. He’s lucky he didn’t go to jail. Maggie seems to be the one who exposed the truth because she was looking out for her brother. She tells him, “I know you blame me. This sucks. I was having such a good night.”
She goes home and ends up sick on the bathroom floor. Lance suggests that he and Milo have a Dude’s Day. Milo points out that Dude’s Day has an entirely different meaning to him. They end up going to a climbing wall and then have a couple beers. Lance is scared that it’s taking so long to have kids and is worried that he might be shooting blanks. Milo says that when they were kids Maggie would hide things like cigarettes around the house. Maybe she’s doing the same thing with some sort of medication. Lance says that Maggie would never do a thing like that.
Maggie goes to the store to buy a pregnancy test because she’s a little late, but changes her mind. She runs into an old classmate who has a terrible kid. They hang out a little bit. Her friend says she isn’t surprised that Maggie is married because Maggie always had a lot of boyfriends. Maggie breaks down in tears and runs to the bathroom. While in there, she buys a tampon. She isn’t pregnant.
Maggie buys some goldfish for Milo and tells Billy that it’s over, for real this time. She goes home and discovers that Lance has found her birth control pills. She confesses that she’s been cheating on him. She goes outside to confront Milo. She yells, “You ruined my marriage.” He points out, “If you think that’s marriage, you’re fucking nuts.” She says that next time he tries to kill himself he should cut deeper. She goes back inside and finds the goldfish she bought and forgot in the plastic bags have died. She tries putting them in an aquarium, but it doesn’t work. She throws the aquarium on the ground.
Milo asks Rich if he’s gay. Rich says that he can make it work with his girlfriend. He also asks if Milo read his script. Milo says it was great. Maggie leaves Milo a voicemail that says, “Dad saw a way out and maybe you did too. See ya later.”
Maggie goes to the pool where she had scuba lessons and waits for everyone to leave. Once it’s empty, she ties weights to herself and jumps in the pool. Before she drowns, Milo jumps in and saves her. She buys him new fish.
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