A panicked young woman, with her reluctant friends in tow, rushes to Mexico to try and delete a ranting email she sent to her new boyfriend.
Wesley Darya has just met Jared Sterling, the guy she thinks is the man of her dreams. After thinking he was ghosting her after not hearing from him for five days, Wesley and her friends Brooke and Kaylie get drunk and send Jared a long and aggressively vulgar email. When Jared calls back and explains that he was in a coma after being in a car accident, Wesley realizes her mistake and drags her friends to Mexico to find Jared’s belongings and delete the email.
While in Mexico, Wesley gets herself into trouble by constantly crossing paths with a mother and son and getting into situations where the mom thinks Wesley is trying to seduce her son, but the boy develops a crush on her. Wesley also encounters Sean, a failed blind date that ends up developing a close friendship with her as he learns about why she is there. However, Brooke and Kaylie feel neglected as they have to keep putting up with Wesley’s crazyness. After she ditches them, they come to personal revelations about their own lives (Brooke wants to leave her unsupportive husband and Kaylie wants to adopt since she and her husband have had trouble conceiving).
Eventually, Wesley finds Jared and almost deletes the email while he is passed out, but she listens to advice from Sean and shows him the email, thinking he will accept her at her best and at her worst. She is very wrong, as Jared is freaked out by the email and dumps her.
Upon returning home, Wesley is alone but gets a job as a guidance counselor at a middle school after Sean recommended her. She reconciles with her friends and then goes to find Sean to pursue a relationship with him.
Wesley is struggling to find a job and a partner and desperately wants to settle down in life. She goes on a date with a man named Sean. However, Sean ends the date abruptly when she mentions marriage and kids too frequently. Immediately after that, she slips, falls down, and meets a charming man named Jared (Robbie Amell). Jared seems like the perfect guy and Wesley starts to hide her true self in order to make the relationship work.
After Jared and Wesley finally have sex, the former does not contact her for a few days. Upset, Wesley gets drunk with her friends and writes a long and insulting email to him. However, Jared calls Wes after that to inform her that he had gotten into a car accident in Mexico, without having checked the email. To save her relationship, Wesley decides to go to Jared’s hotel in Mexico, sneak into his room and delete the email. She takes her friends, Brooke and Kaylie along.
Coincidentally, Sean is at the same hotel. Wesley gets chucked out of the hotel due to a few mishaps. However, she tries to break in again (against her friends’ advice), gets caught, and is jailed. After her release, Sean comes to pick her up. Wesley decides to meet Jared at the Mexican airport and fly back with him. She plans on deleting the email on the flight. Sean agrees to drive her to the airport. On the way, Sean tells Wesley that she had been his first and only date after the death of his wife. He had ended the date because it had gotten too real too fast. The two bond over the drive.
On the plane, Wes tells Jared about the email and comes clean to him. However, Jared breaks up with her since she had been hiding her true self. After that, Wes ends up fighting with her friends since they feel neglected by her. Back home, Wes finds a job due to Sean’s recommendation. Then, she apologizes to her friends and they forgive her. Wesley goes to Sean, who is at the restaurant where they had gone on a date, to ask him out. However, Sean is on a date with another girl. Yet, he agrees to date Wesley and the two kiss on the street. The other girl walks past them, complaining to her mother about her terrible date.
The film starts with Wesley Darya (Nasim Pedrad) going to a job interview for a guidance counselor position at a Catholic school. She bombs the interview when she starts getting too candid about sex talk with the head nun. Wesley’s friends Brooke (Anna Camp) and Kaylie (Sarah Burns) try to cheer her up at Kaylie’s house, only for a broken transformer to fall on Wesley’s car.
Wesley decides to go on a blind date with a friend of Kaylie’s husband Tad (Scott Rodgers). She meets the guy, Sean McGuire (Lamorne Morris) at a bar. Although they chat and joke briefly, Sean decides to take his “automatic out” because Wesley was going too fast by talking about marriage and kids. She responds with how she has had a very bad year with trying to find a job, her ex getting married, and her birds dying. As she storms out, Wesley’s heel gets caught in a crack and she trips and falls unconscious. She is woken up by a handsome stranger named Jared Sterling (Robbie Amell). He invites her back to his place so her friends can pick her up there.
Wesley likes Jared a lot, and he seems to be attracted to her, so at Brooke and Kaylie’s behest, she decides to see him. They start dating for about a month, and they end up having sex. After a few days, Wesley doesn’t hear from Jared, and she thinks he is ghosting her. She gets drunk with Brooke and Kaylie, and they all write Jared an angry email with references to his dead dad and him having a small penis. As the ladies try to find a signal to send the email, Wesley gets a call from Jared, who says he was in a coma for the last few days in Mexico after getting into a car accident. His phone and laptop are at his hotel, and Wesley realizes she has made a horrible mistake. Unfortunately, the email has already gone out. Desperate to fix things, she proposes to her friends that they go to Mexico and break into his room to delete the email. Although they are reluctant at first, Brooke and Kaylie agree to go.
The ladies arrive in Mexico at the resort where Jared is staying. They make a bad first impression when Wesley’s bag falls and a dildo falls out, which is picked up by a boy named Nolan (Toby Grey). His mom Debbie (Jessica Chaffin) is pissed at Wesley, who awkwardly tries to get away from the situation. To her surprise, Sean is also there, but she tries to avoid him.
Without a clear plan on how to get into Jared’s room, Wesley calls his phone until she hears his ringtone. When trying to use a card to open the door fails, she has Brooke and Kaylie help her pretend to need assistance getting back into her room while she is only wearing a towel to make it look urgent. The resort employee knows it’s not her room, but after Wesley begs him, he relents and lets her in. Unfortunately, the room belongs to Debbie and Nolan, the latter thinking Wesley is now his girlfriend and that they have a connection. Two instances occur in which her towel falls off and Nolan almost sees her, but when he tries to return the towel while covering his eyes, he accidentally touches Wesley’s breast. Debbie comes in and sees and thinks Wesley is a pedophile.
Meanwhile, Brooke and Kaylie go out together since Brooke is feeling neglected by her husband back home. They spot two men that they decide to hang out with. Kaylie befriends one guy because he’s gay but the guy Brooke talks with is a total loser. Wesley returns to them while wearing a towel that is barely covering her.
The next day, Brooke and Kaylie tell Wesley they learned that the resort’s manager, Quintano (Izzy Diaz), takes guests paddleboarding and leaves his stuff on the shore, so they may have an opportunity to swipe his master key. While Wesley attempts to wait for an opportunity, she is met by Sean, who tries to get Wesley to go paddleboarding with him. Since Brooke and Kaylie can’t, Wesley reluctantly joins him. They make it to the dock and hang out where they see a dolphin. Wesley is amazed by it until the dolphin swims to her and starts humping her. Not long after, it jumps back out and slaps her in the face with its penis. Sean carries a traumatized Wesley to the shore, where Brooke tells her they got the master key.
While walking back to the hotel, Wesley feels sick and passes out. Nolan happens to be there and tries performing CPR on her, but she pushes him off. Debbie attacks Wesley for thinking she was once again harassing her son, but Wesley then barfs on Debbie’s face. This leads the three friends to get kicked out of the resort. They are forced to stay in a rundown motel in a dangerous part of town. Wesley, still desperate to complete the task, tickles Brooke to get her to give up the master key before Quintano changes the codes to Jared’s room.
Wesley runs back to the resort where she gets electrocuted trying to climb a fence. She does manage to make it to Jared’s room and gets a call from him saying he will be heading home early. Quintano and his assistant catch Wesley in the room. She attempts to jump out the window to escape but is caught. Brooke and Kaylie have arrived to find her and watch her being arrested. The two go to the jail to bail Wesley out along with Sean, but to their surprise, Nolan is the one who bailed Wesley out because he loves her so much. After Wesley gets out, she appears to have a moment of clarity on how insane the whole trip was, but she instead just has a different plan on getting close to Jared and erasing the email when he’s not looking. Brooke and Kaylie become concerned for Wesley’s behavior and try to help her out, but she remains stubborn and drags Sean into the mess. Brooke and Kaylie decide to go off on their own.
The two ladies decide to go to a meditation resort led by a guru Kaylie follows named Angel de la Paz (Heather Graham). After a bus ride to the place, the two meet Angel, and Kaylie expresses her desire to have Angel help her get pregnant since she has been having trouble doing so back home. Angel says she cannot do anything for her, despite her having a reputation for helping women. Angel decides to see Brooke alone, and while Brooke doesn’t like how Angel spoke to Kaylie, she is able to open up to her about her frustrations with her husband back home, leading Brooke and Angel to start hooking up. Kaylie, however, is depressed and gets drunk. On the ride back to their motel, she tells Brooke she never liked her husband and supports her next move.
Wesley and Sean find Jared being escorted to the airport by hotel employees, who are carrying his electronics out to bring back to the airport. The two decide to follow the hotel van, and they start bonding more on their trip. Wesley talks about how much she loves Jared, but when she gets down to it, all she really likes is that he’s attractive, and he said she’s the “last normal girl in LA,” which Sean disagrees with since he knows Wesley is anything but normal. Their trip is derailed when a goat standing in the middle of the road causes their car to turn over, but they are unharmed. They find the place and see it is a quinceañera, so they actually enjoy the party and hang out together. He joins her on a van that takes her to the airport so she can “conveniently” bump into Jared and guide him home after claiming that she flew to help him.
Wesley joins Jared on the plane ride home, while also seeing Brooke and Kaylie and passively ignoring them. Wesley tries to get Jared to fall asleep so she can delete the email from his phone, but she remembers that Sean told her she should let him read the email so that he can see her at her best and at her worst. Wesley wakes Jared up and shows him the email. He is understandably horrified and tells Wesley he doesn’t want to be with her anymore, and Wesley is now alone and miserable. Even when they land back in LA, Brooke and Kaylie are too tired of her drama to deal with her. They announce that Brooke is getting a divorce and Kaylie is going to adopt a baby.
After some time, Wesley gets a call from a school saying that Sean recommended her for the guidance counselor position. She goes to the school and makes a good impression on the kids and staff, allowing her to earn the job. Still feeling bad about neglecting her friends, she goes by Kaylie’s house and finds her cat Kevin (who is repeatedly mentioned as looking like Hitler) wandering outside the house. Wesley climbs the tree in the yard to retrieve Kevin, when she sees Kaylie and Tad talking in the house with a pregnant woman. She falls from the tree and is met outside by Kaylie, Tad, Brooke, and the pregnant woman. Wesley explains herself and apologizes to her friends for her behavior and tells the woman that Kaylie and Tad will be great parents for her baby…but it turns out that she is a real estate agent and Kaylie and Tad are just selling their house. Wesley is embarrassed, but her friends forgive her.
Wesley then goes to the same restaurant where she met Sean and tries to explain that she was wrong about Jared. However, Sean is on a blind date with another woman and says he only wants something casual instead of a relationship. As she excuses herself, Wesley tells Sean how she really feels and leaves. The other woman returns and tells Sean a crazy story, so he runs back outside to Wesley and kisses her. The other woman comes out and is pissed, telling her friend that this always happens to her.