Plot
Alex Rose's mother Elizabeth tells her her cancer is back, and metastasized. Elizabeth fears Alex is settling into a life out of obligation.
Elizabeth's will reveals Alex no longer has a job at Rose Cosmetics, and her sister-in-law is the CEO. Her house will stay off the market for a year, so available to them for now. Each get 20% of the company's shares, but Alex's inheritance will be divulged after completing set tasks.
Once alone, Alex watches her mother's video explanation. Elizabeth wants Alex to follow the life list wrote at 13. After completing the tasks, her inheritance will be unlocked. Young lawyer Brad Ackerman, the will's executor, will verify each task's completion then give her the subsequent video.
Alex is given a true love test to determine if she is truly in love. Its four criteria are: 1) if she can fully open her heart to the person; 2) that he is kind; 3) that he inspires her to be her best self and 4) she could envision him as father to her future children.
After Alex shows her boyfriend Finn the list, he enthusiastically envisions them jointly owning a gaming company where they both would work. Appalled, she leaves. Alex later approaches Brad, accepting her mother's challenge.
At a comedy club open mic night, Alex effectively shoots down a heckler. She then is challenged to get out of her comfort zone daily for a week. Brad gets her to volunteer teach high schoolers in a shelter. Encountering difficulties with a student, Alex is taken to the shelter's coordinator, Garrett Taylor. Having briefly met on the subway, he gives her advice on dealing with the youth.
At a peace-making dinner with her estranged father Sam, Alex inadvertently discovers she is the result of her mother's affair with musician Johnny Alvarez. Meeting with her brothers, Alex proposes finding him, which her brother Lucas supports, whereas Julian discourages her to avoid public scandal.
To learn to play Clair de Lune, Alex enlists her childhood piano teacher, who accepts on the condition that she participate in a group recital. After another failed attempt to connect with the challenging student, she again goes to Garrett. However, as he has a charity event to attend, she tags along. Brad is also there with his girlfriend Nina, who is soon to be moving back. Seeing Patrick Ewing, Alex gets an introduction so charms him, as Garrett and Brad talk about her.
Dating Garrett, Alex gets Ewing to participate in a charity event, where they shoot hoops together, ticking more items on the list. When she unhappily points out to Garrett their activities focus on him, she gets him to come to a dinner party at hers. Afterwards, they argue because he was uncomfortable with her rambunctious friends for some of the things they said. He further accuses her of only being with him to finish the list for her inheritance, then leaves angry.
Without her ride, Brad and Nina drive Alex to surprise Johnny at a gig in Vermont. Booking adjoining rooms, Nina notices their chemistry, so quietly leaves. Alex and Brad go to the gig, and Johnny comes over between sets as they were staring. They chat, agreeing to meet in the morning. Alex and Brad go drinking afterward, then later are intimate.
In the morning, Johnny is a no-show. Saddened, but unsurprised, they ride back to NYC in silence. Alex thanks Brad as they pull up to her building. He kisses her, then she chastizes herself for believing meeting her birth father would fix things. Brad goes on to praise her, she calls their intimacy a mistake, then he reveals that he and Nina broke up over her. Upset he had not told her before they slept together, Alex sees Garrett so starts to leave. Brad tells her he does not believe she loves Garrett. She angrily gets out of the car.
However, Alex talks with Garrett in her building. Although he says he missed her, she tells him that what he had disliked that night in her apartment are essential elements of her. Alone again, they both move on.
Lucas gets Julian and Alex to meet at the house, believing it is about its sale. He surprises them with an impromptu campout under the full moon. Both initially object, but end up staying. Alex tells them about the Vermont trip, and her brothers make her aware that they were all envious of her close bond with Elizabeth. She shares the videos of their mother with them.
Alex meets with Sam again, and they reconcile. When she goes to the law office in December, she expects both to see Brad and be told she will not receive her inheritance as she did not complete the list. Regardless, Alex receives her inheritance, the deed to the house. In her final video, Elizabeth asks her to strive for true love, and she watches them together.
Alex apologizes to Brad, confessing that the last time they spoke she felt overwhelmed. She insists he fulfills the four criteria of the true love test, and they embrace.
Alex invites everyone over for New Years, where Julian toasts to old friends and new, thanking their mother for helping them get through the year.
