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Alex is reluctant to go to her sister's baby shower. She knows her family will just bombard her with the usual questions—why she isn’t married to her boyfriend, Finn, yet, and why he’s only working at a record store.
Meanwhile, Finn heads up to her room, strips down, and starts dancing to "Buttons," expecting Alex to walk in soon. But instead of Alex, her sister's kids walk in. Awkwardness ensues.
At the end of the night, Alex talks to her mom, with whom she has a great relationship. She even works for her mom's company. But then her mom drops a bombshell—she’s dying.
Cut to some time later: Alex is lying in bed alone. Her mom has passed.
She heads to the lawyer's office for the reading of the will. Expecting to see Old Man Sullivan, she’s surprised when a young lawyer named Brad walks in instead. And Brad only brings bad news. First, Alex and her family must keep the house for at least a year and can't sell anything inside it—not that she minds. But she’s shocked to learn that her mom made her sister-in-law the new CEO of the business. As for Alex, she won’t receive her inheritance right away. Instead, Brad hands her an envelope with instructions to open it when she’s alone.
Back home, she puts in the DVD from the envelope. Her mom appears on the screen, explaining that she wants Alex to live her best life, starting with completing her old "Life List." Every time she checks something off, she’ll receive another DVD from her mom. And when she finishes the list, she’ll get a final envelope. What’s inside? Who can say.
Determined to start fresh, Alex breaks up with Finn. She begins tackling the list—reading Moby-Dick, learning the piano—but it’s harder than she expected. So, she pivots, tries stand-up comedy, and earns her first DVD.
Meanwhile, Brad keeps showing up, being unexpectedly nice to her.
She’s starting to enjoy herself overall, but then she reconnects with her dad—only to learn he’s not actually her biological father. Her mom had an affair with a man named Johnny Alvarez. He is her real father.
She starts working at a school and meets a guy named Garrett. They start dating, and things are going great—until she throws a dinner party with her friends, and Garrett hates them. That’s… unfortunate.
After a long search, she finally tracks down Johnny. She takes a road trip with Brad and his girlfriend, Nina, to meet him. But Nina starts sensing something between Brad and Alex—and she’s right. Nina eventually heads home, and Alex and Brad end up sleeping together.
The next morning, Alex meets Johnny, and they agree to get breakfast the following day. But he never shows up.
On the way home, she and Brad get into a huge fight. He tells her she should break up with Garrett because "that guy sucks." She does. Then, in frustration, she tears up her list—after all, the only thing left is to "find true love."
But then Old Man Sullivan gives her the final DVD and envelope anyway, and it’s all very sweet.
Finally, she realizes—she does love Brad. She goes to find him. They kiss.