At the beginning of the movie, Burt (John Krasinski) speculates that girlfriend Verona (Maya Rudolph) is pregnant due to a change in her "vaginal flavors." After the title shot, Verona is six months pregnant. The couple visits Burt's parents, Jerry (Jeff Daniels) and Gloria (Catherine O'Hara), for dinner, who excitedly break the news they are moving to Belgium in June. Burt and Verona are shocked at the random announcement, as the baby is due in July and the reason they moved to Colorado was to be close to family. Jerry and Gloria are still too excited about their move to be concerned, seeing the positive that if they can't get their house rented for the next two years, Burt and Verona can live in it. Burt and Verona are devastated that Jerry and Gloria are okay with being away from their grandchild for two years, but Jerry and Gloria (still excited) simply state they can fly back to visit. Gloria gets a phone call from their realtor and discovers they have someone who will rent the house. Jerry and Gloria are even more thrilled, while Burt and Verona try to absorb the situation.
Burt and Verona (both in their mid 30s) contemplate what they should do, since they agree they want to be near friends and family for having the baby (it is mentioned Verona's parents passed away when she was 22, explaining why they moved to live by Burt's parents). Verona says they can move anywhere, since Burt would be able to get a job (he works in insurance) and she can do her work from anywhere (she illustrates medical conditions). They rule out Chicago, since they used to live there, and Verona brings up Arizona where her sister and former boss (from Chicago) live. Burt and Verona agree to fly out to Arizona, which begins a travel search to find a new home including visits to Phoenix, Tucson, Madison (WI) and Montreal. There are title shots throughout the movie to indicate the change in location.
("AWAY TO PHOENIX") They arrive in Phoenix, and are met by Verona's former boss, Lily (Allison Janney), her husband Lowell (Jim Gaffigan) and their two children, Ashley and Taylor. The family takes Burt and Verona to a sparse racehorse track followed by a diner. Lily is energetic, loud and unedited while the rest of the family is mostly quiet and introverted. Throughout the visit, Lily thinks nothing of making uncomfortable and disparaging comments about her children (who are nearby) and husband Lowell is too miserable to pick up on it. Lily says people in Phoenix are very "clique-ish," and doesn't understand why her and Lowell were unable to get membership into the country club. When departing from the family in the parking lot, Lily hangs back to give Verona a hug goodbye. As Verona walks to the passenger side, Lily gives Burt a hug goodbye, then suddenly jolts her head forward and kisses him. Burt struggles to push her off, and silently walks to the drivers seat.
The next day at their motel room, Burt returns from his job interview and tells Verona it went well. While he wasn't offered a job on the spot, he expects to hear something formally in the next few days.
("AWAY TO TUCSON") Burt and Verona travel to Tucson, where they visit Verona's sister Grace who works as a concierge/guest representative at a hotel/resort. While waiting for Grace, Burt and Verona sit in the lobby area, where a mother quizzes her young son about things he knows. The mother points to different objects, and then points at Verona's tummy. The boy says "baby" and the mother asks the boy to tell the nice lady what he knows about babies. The boy hesitates, before saying that babies are strong breathers. The mother looks puzzled, but the young boy continues that once he held a pillow to a baby's head and expected it would stop breathing, but the baby was sneaky and he would get it the next time around. Stunned and embarrassed, the mother rushes her young son away from Burt and Verona. As that happens, Grace finishes with a guest and meets with Burt and Verona for lunch.
Later on, Verona accompanies Grace as she shops for a spa tub. Verona shares her concerns about motherhood. Grace has Verona climb into a tub with her as she comforts her sister. Grace asks Verona if she has visited their parents' house yet, but Verona says she hasn't since their passing. The thought is still too painful for Verona to bear. The sisters reminisce about the past and Grace reassures Verona about being a future mother.
("AWAY TO MADISON") At the airport check-in, the attendant at the desk reminds Verona that women who are eight or more months pregnant must have a doctor's note of approval to fly. Verona explains that she understands, and she is only six months pregnant. The attendant asks a co-worker for their opinion, who also does not believe that Verona is only six months pregnant because of her large size. Finally the attendants get their supervisor (Christine Baranski), who also asks for medical documentation, unconvinced Verona is anything less than eight months pregnant. Burt and Verona are forced to take a train to Madison.
As they board, Burt tries to see the positive of riding the train ("maybe we'll see buffaloes!"). Sitting in a booth on the meal car, Verona checks on the baby's heartbeat with a portable device. She comments the baby's heartbeat is a little slow. Burt makes some agreeable comments, and Verona brings up that they should argue more, or at least Burt should raise his voice to get the baby a little more riled up. After a moment, Burt yells, "You cunt-sucker!" at Verona, attracting shocking looks from everyone on the train. Burt takes the device to excitedly check on the baby's heartbeat. (Burt taking opportunities to surprise Verona and raise the baby's heartbeat and then check using the device becomes a recurring stint for the rest of the movie) Later on in the evening in the sleeper car bunks (Burt is on the top bunk, Verona on the lower bunk), Verona comments on being so huge and has concerns on remaining big. Burt comes down to comfort her, letting her know that no matter what her size, he will always love her-- even if she gets so huge that he can't find her vagina (this too becomes a recurring joke).
In Madison, Burt and Verona are walking through a university campus to meet one of Burt's childhood friends, Ellen (Maggie Gyllenhaal). They ask a woman with a stroller if they know where Ellen's office is, she says she does and points them in the right direction before briskly moving on. Burt and Verona find her office door, and notice the nameplate reads "LN" and proceed to knock on the door. Ellen asks them to enter, and as Burt and Verona do, they see that Ellen is standing at her desk, comfortably breastfeeding her children (one is an infant, the other a young toddler). Ellen appears to be unashamed to be breastfeeding openly in front of Burt and Verona. They awkwardly wait for Ellen to finish, and then they all walk outside. As they walk, Ellen (whose infant is wrapped in front of her) chats mostly with Burt while Verona struggles to keep up with them. Ellen talks about things that leave Verona mostly out of the conversation, and also explains that she knows the woman that gave Burt and Verona directions to Ellen's office. Ellen once babysat her child, and breastfed him to calm him down, not thinking much of it. The woman was upset, and Ellen didn't feel she needed to be so.
Later on, Burt and Verona come to Ellen's house for dinner. At the door, Burt and Verona have brought a stroller as a gift, and hide it on the porch for now. Ellen opens the door and greets them, and has them take off their shoes and put on slippers (Verona puts on fuzzy animal ones while Burt puts on elf shoes). Burt goes to get the stroller, and Ellen seems devastated at the gift. Ellen orders Burt to put the stroller back outside on the porch. Ellen takes Burt and Verona to the bedroom to meet her husband, Roderick (Josh Hamilton). Roderick is comfortably seated in the middle of an elaborate, bohemian styled bed, holding their infant son who is napping. Ellen climbs into the bed next to Roderick, while Burt and Verona simply stand in the room, puzzled at the situation and what to do. Burt asks questions, and Ellen and Roderick seem caught off guard at having to explain their lifestyle philosophies, including 3 S's: no sugar, no separation, no strollers (Ellen: "Why would I want to push AWAY my children in a stroller?") and living a "continuum" lifestyle (Verona: “What’s a continuum?").
At the dinner table, the conversation shifts to Burt and Verona's occupations, and Roderick is seemingly disgusted at the idea of working in insurance (Burt's occupation). Burt then pointedly asks what Roderick does, which seems to have hit a sour spot (Ellen has a trust fund they mostly live on, Roderick doesn't really have to work), and Ellen tells Roderick to calm down since Burt and Verona come from poor, less privileged backgrounds, and they should not expect Burt and Verona to understand the same things Ellen and Roderick can. Burt is outraged, and starts calling out on Ellen and Roderick's insane behavior, and is fed up with trying to act polite to them. Burt storms off the table, and Verona follows suit, taking off her bootie-slippers, saying she hates them. As she does, Burt returns to the table with the stroller, and walks towards the toddler at the dinner table with a smile. Ellen and Roderick, still sitting at the table, protest Burt and plead with the toddler to not get in the stroller. The toddler hesitates, then smiles and climbs into the stroller while Burt runs him around the house, chased by Ellen and Roderick.
("AWAY TO MONTREAL") Burt and Verona travel to Montreal, to visit old college friends, Tom and Munch (who are married). On the porch, Burt and Verona are impressed at their friends' house, and how "grown-up" it is. As they enter the house, Burt and Verona continue to be awed at how obviously well put together the home is, and in the living room are several children watching The Sound of Music. It's the "So Long, Farewell" scene in the movie, where the children sing and bid goodnight to the party guests as they go upstairs to sleep for the night. The two youngest children in the living room act out and sing along with the scene for Burt and Verona, who are visibly impressed. Tom and Munch return to the room to get the children for lunch, and Tom explains to Burt and Verona that they haven't let them watch the second half of the movie quite yet, due to the heavy topics involved.
The scene changes to where the two couples (Tom and Munch, Burt and Verona) are enjoying themselves, driving around town at night. Burt and Verona explain that they are very taken by Montreal, and are confident this is where they want to move. They come to a local diner-looking restaurant, where Tom and Munch ask why Burt and Verona aren't married yet. Burt explains that he has proposed to Verona several times already, and even asks her to marry him again to show Tom and Munch, and Verona confidently turns him down. Verona explains she simply doesn't understand the need to get married, and that she is very happy with Burt and knows they are committed to each other. Tom respects the situation, and explains that really all you need is love, as it is the glue that keeps a family together.
Later on at a bar, Munch and Verona chat away from Tom and Burt, who are watching performers on stage (it's "Amateur Night"). Munch asks Verona if she is having any complications with her pregnancy so far, and Verona says no. Munch is happy for Verona. Meanwhile, Tom and Burt are talking, when they see Munch take the stage. She starts dancing around the pole, in a depressed and vulnerable way, with constant eye contact at Tom. Tom explains to Burt that Munch had another miscarriage, just the other day. This was her fifth miscarriage. Tom knows that Munch loves all five of their adopted children as any mother could, but there is tremendous pain in not having her own child.
The next morning, Verona wakes up to hear Burt talking on the phone, under the bed. Burt tells the person on the phone they will be on a plane first thing once Verona wakes up. Verona asks who it is, and Burt explains that they need to visit his brother in Florida, as his wife has suddenly left him.
("AWAY TO MIAMI") Verona and Burt fly to Miami to see Burt's brother, Courtney. On the plane, Burt attempts to scare Verona again, and checks the baby's heart rate with the device, while Verona politely apologizes to the other people on-board. Burt and Verona arrive in Miami, and are met by Courtney and his young daughter, Annabelle. They all walk about at night, and Courtney explains the situation to Burt-- Courtney thought his wife hadn't really left, so he simply told Annabelle that her mom was away visiting someone and would be back in a week; then after a week, he realized his wife wasn't coming back-- he tells Annabelle that her mom is still away, as her father passed away (he really didn't). Courtney is lost as to how explain the situation to Annabelle-- he asks Burt if it would be wrong to say that she was murdered. Burt says of course he can't say that kind of a lie to a child. Courtney is still lost as to what to say to his daughter.
In the evening, Burt and Verona act out a story using stuffed animals for Annabelle, who enjoys it as she is in bed preparing to go to sleep. After they finish, they say goodnight to Annabelle, who asks if Verona can stay by her a little longer. As Verona sings Annabelle to sleep in her room, Courtney shows Burt school photos of Annabelle. Courtney reminisces their childhood, when it would take weeks to get school photos, whereas now they are done within a week. On second look, Courtney notices a carrot juice stain in the photo. He says he must have missed it when Annabelle went out the door the morning of the photo. Courtney distresses, saying a mother would have caught such a detail, and begins to breakdown at the thought of all the things Annabelle won't have growing up without a mother.
Later on, Verona goes into the backyard to see Burt on the trampoline, jumping while talking on the phone. Burt explains to the person on the phone he knows it is a late hour, but he wouldn't be calling if it weren’t important. It turns out Burt is calling everyone in the family's phonebook to see if they know anything about the whereabouts of Courtney's wife. Burt tells Verona he can't understand why a mother would abandon her child, and how unfair it is to Annabelle that she will grow up without her mother. Burt begins second-guessing their lives, and makes Verona promise that she will never leave their child, which she promises. Burt asks Verona why she just doesn't marry him, to give him peace of mind-- he understands that she doesn't want to get married without her parents there, but he feels it's important to do so. Verona says she won't, and climbs onto the trampoline to assure him that she will always love him and never leave, regardless of not being married. He promises the same. They rotate asking each other promises for their future (including to NEVER follow Ellen and Roderick's philosophies on seahorses), akin to marriage vows. They fall asleep on the trampoline.
The next morning, Burt wakes up on the trampoline to see Verona is missing. Burt sees her sitting on a bench close to the orange trees in the yard, and walks over. Verona explains that her dad planted an orange tree once. Her father would tend to it well, but it would never bear any fruit. One day, Verona, sister Grace and their mom got a variety of different fruits and stuck them on the tree. Verona says her dad stared at it for a good minute, possible thinking the tree really did have an overnight growth of a fruit variety, but probably realized it wasn't the case once he saw the pineapple on the tree. Regardless, her dad went with it and was proud of his family for the tree's progress. It became a family tradition to hang the most ridiculous things on the tree.
("HOME") Burt and Verona are driving in their own car, with all their things through a coastal countryside. The car approaches the entrance to a homestead, and as they turn in Verona sees the tree with random things still hanging from it. They drive through a small orchard and then stop in front of a large white house. Verona comments it's still as beautiful as she remembers it. Burt and Verona walk to the front of the house, unlock the door and slowly step in. Verona takes it all in, while Burt moves slowly forward to another set of doors. He opens it, revealing the outside at the other end of the house, facing the water and sunset. Verona comes next to Burt, and they both sit on the steps, staring out into the water and sun. Verona feels they are home, at last.
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