After he receives a new cancer diagnosis and she is fired from her job as a sex columnist, Bailey and Darla take a road trip that forces them to get intimate with their issues, as well as each other.
Bailey (Sam Richardson) and Darla (Brittany Snow) embark upon a misguided and mutually deceitful form of therapy, one in which they must drive across the country re-enacting Darla's colorful history as a sex addict. As their true motivations for the road trip come to light, the unlikely pair force one another to confront their issues and discover that there might actually be more to love than just sex.
Darla (Brittany Snow) is a sex addict and attends an addict support group at a local high school. Bailey (Sam Richardson) attends a cancer support group at the same school. Bailey is due for his annual checkup after his testicle removal surgery an year ago.Darla has sex with people who attend the support groups, by hooking up with them in empty classrooms at night. Darla insists that she is not an addict and only attends the support group to conduct primary research for her magazine column which focuses on the topic of female orgasm.
Darla is fired by her boss at her office Tanya (Jordana Brewster) for having sex with an intern (she has a video clip as evidence). Tanya says that Darla was recently embroiled in a sexual harassment complaint at the workplace and now her writing is also going downhill.
Bailey works at a gym, cleaning and maintaining the equipment. Meanwhile Bailey gets news from his doctor that his cancer has re-emerged. Bailey had testicular cancer and already had his left one taken out. Now there is a lump in the right one and needs to be chopped off.His girlfriend Elizabeth (Anna Akana) breaks up with him saying that they both need to be with other people before they know they are right for each other. Bailey and Elizabeth's parents are friends, and Bailey's parents are big fans of Elizabeth. Bailey hasn't told his parents about the break-up.
Darla is a column writer and needs to find a top story to save her job. After a meeting with Elizabeth (where Bailey realizes that she is already dating other people and she declares that she is going home for her mother's retirement party), Bailer gets drunk and accidentally enters Darla's support group, she takes him out to see if she can get a human angle story out of him.While talking, Bailey notices Darla carrying the map of USA. Darla explains that their group leader made them mark all the places where each of the group participants had sex, as a way of healing and making progress.
Bailey suggests that Darla visit all the places she had sex in, to cure herself and she agrees (she is only looking for the story). The idea is that she will have sex with Bailey in all the places where she first had sex. Bailey sees a video of Elizabeth on Instagram inviting people to attend her mother's party. Bailey agrees, on the condition they visit Dallas, where he hopes to reconnect with Elizabeth. Unbeknownst to Bailey, Darla persuades her former editor, Tanya, to let her publish a daily blog about the trip. Darla convinces Tanya that Bailey is the story, and lies that Bailey knows that Darla would be writing about it. Tanya agrees as she needs a powerful piece to showcase the power of the internet to her conservative board of directors, who are not willing to let go of the print medium.But Tanya refuses to cover Darla's expenses and says that if the piece is a success, she will consider taking her back.
They start the next morning and Darla brings a map full of X's. She has sex with Bailey in exactly the same places and the same way where she had sex before. She finds out that Bailey had a testicle implant after the removal of one of his testicles previously. While Darla will have sex with Bailey everywhere, but she sleeps on the couch in motels and won't share a bed with him. She writes her blog in the bathroom, hiding it from Bailey.She keeps a daily blog on her computer and her online account, not shared with Tanya yet. Darla is reluctant to go to her own house (where her parents live, as that's also marked on the map), but Bailey forces her to. Darla admits that she has sex with a married man and his wife walked in on her and gave her the dirtiest look she ever got from anyone. Yet, at the time, she had no remorse from her actions.Darla discovers Bailey's passion for drawing, and he considers not going through with the surgery.
In Dallas, Darla is forced to pose as Bailey's girlfriend and meet his parents, who are dismissive of his art; his mother, Cindy (Vivica A. Fox), hopes to reunite him with Elizabeth. Sneaking into Elizabeth's childhood bedroom to recreate losing his virginity, Bailey and Darla spend a romantic night together, kissing for the first time.He discovers her blog before they attend a party at Elizabeth's parents' house, where Elizabeth inadvertently reveals Bailey's posts portraying Darla as his girlfriend. Darla confronts him for using her to make Elizabeth jealous, and he accuses her of using him for her blog, disparaging her writing and sexual past. She humiliates him with the truth in front of Elizabeth and his family, and storms out.
Elizabeth reconnects with Bailey, and he tells her of his new diagnosis. They prepare to return to Atlanta together, but she upsets him by revealing his diagnosis to their parents. Darla has sex with a man she meets at a bar, before angrily sending him away. Visiting her mother, Betty (Amy Pietz), who shares her destructive behavior, Darla struggles with her final blog post. She is touched to discover Bailey's drawings on their map, and her mother rejects her attempt to discuss addiction.
Arriving in Atlanta, Bailey realizes that he and Elizabeth have outgrown their relationship, and they amicably part ways. Darla makes peace with her mother, who fixes her car, and she arrives at Bailey's support group just as he is describing his appreciation for her. They reconcile, and he undergoes his second Orchiectomy, while she commits to treating her sex addiction.
Agreeing to remain platonic friends while they help each other through their recovery, Bailey finds a job as an illustrator, and Darla is offered her job back due to the popularity of her blog, but declines and receives an advance to write her own book. One year later, Bailey's cancer is in remission and Darla has spent a successful year in recovery, and they agree to go on a date.
