Watch on Philo! - Philo.tv/DTH *Producer note: a listener has explained to me how PO boxes work* A woman walks into a bar as Oliver narrates over the scene. We see that she ends up in the background of a selfie while she’s walking around. She sits at the bar, writes a letter, and puts a stamp on it. When she notices the cops looking around, she quickly leaves, causing the letter to fall to the floor and get kicked under the bar. Fast forward five years: the gang is at brunch. Ramon brings them a letter he found under the bar — it turns out this brunch spot and the nightclub from five years ago are one and the same. They can't make anything out from the outside of the letter, so they open it. Unfortunately, the letter couldn't be less helpful — it's even signed "Me," almost as if it’s written in code. We also find out that Shane and Rita are both pregnant! Yippie! Oliver and Shane go to tell Oliver’s dad that they’re expecting. Oliver is also working with his dad to open a postal museum. While going through the attic, Oliver’s dad finds a box labeled "For Oliver Someday" and quickly tries to hide it. The next day, they're back at the office when Charley reads the letter and immediately realizes that the author is talking about the now-famous artist Nate Hallaway. Shane looks him up and sees he’s playing a gig in Vegas. ROAD TRIP! Oliver and Shane go to a doctor’s appointment, and everything is looking good with the baby. However, Oliver realizes he knows very little about his family history. He goes to talk to his dad, who then gives him the "For Oliver Someday" box. Meanwhile, the gang makes it to the Vegas show. At first, Nate acts like he doesn’t know what they’re talking about. But after the show, he admits the truth: the letter is from a woman named Tracy Rio. She wrote his best songs. That night, she had suddenly disappeared without telling him why. Since then, she has been sending him songs and he sends money via a P.O. box every month. The team stakes out the P.O. box until someone matching Tracy’s description shows up. They follow her and discover that she’s now a caregiver. She invites them in and shares her story: she’s been on the run ever since her dad robbed a bank when she was a child. Her whole family has been "wanted" ever since. When she turned 18, her mom gave her money and stamps, and they communicated through a postal box. After that fateful night, she assumed the box no longer worked and never wrote again. She asks the team to find her mom and tell her she’s okay. While working on this, Oliver reads through the letters his dad kept and begins to question why his dad held onto them all these years. As he’s processing all of this, Oliver tracks Tracy’s mom to a nearby church. He delivers Tracy’s letter and tells her he must report her to the police. However, he finds out she has another daughter who will turn 18 in six weeks, so he agrees to give her that time before reporting her. Oliver and his dad have a heart-to-heart about fatherhood and reconcile. Six weeks later, it’s time for the gala to raise money for the postal museum. Tracy — whose real name is Lilly — shows up, and her mom is there too. Lilly goes on stage to sing. Meanwhile, Oliver tells her mom that it’s time: the feds are waiting. She turns herself in, and Oliver reunites Lilly and Nate backstage. The movie ends with the gang hanging out, drinking Yoo-hoo, and Rita finding out that the baby they’re adopting was just born — so they rush off together.