You Can't Win 'Em All is the 20th episode of Season 5 on CW teen soap 90210.
ANNIE DEALS WITH THE FALL OUT FROM HER BOOK — Jordan (guest star Robbie Jones) calls in a favor from his mother (guest star Robin Givens) to help out Mark (guest star Charlie Weber), but in exchange must end things with Naomi (AnnaLynne McCord). Annie (Shenae Grimes) must deal with the betrayal Liam (Matt Lanter) feels from being in her book and Michaela (guest star Lyndon Smith) catches Navid (Michael Steger) and Adrianna (Jessica Lowndes) during an intimate moment. Jessica Stroup and Tristan Wilds also star.
The episode begins in the morning with Navid and Liam waking up and wondering about the things that transpired on the previous day. Under his pillow, Navid finds one of Adrianna’s earrings. While dressing up, Adrianna finds one of her earrings missing and wonders where it could be. In the bathroom, Silver looks worried after doing a breast examination. In prison, Naomi and Annie arrive to meet Mark, who has been arrested because drugs were found in his baggage, at the airport. Jordan is with them and Annie tells him, how Patrick must have framed Mark. She recalls that Mark’s suitcase was in the lobby, when Patrick had come to meet her. Annie and Naomi are worried on learning from Jordan, whose lawyer is handling Mark’s case, that this wasn’t Mark’s first offence. In fact, Mark was out on parole for narcotics trafficking. Mark tells the duo that, two years ago, while he was working at a restaurant, the crew there was dealing in drugs. He looked the other way, but when they got busted, he too was arrested. He, plead not-guilty to charges and got away with probation and no jail time. During their conversation, Mark reveals that he has two kids with his ex-wife. He says he hasn’t been a good father all these years and has hardly spent any time with them. Which is why, he had promised to celebrate one of his kid’s 11th birthday this weekend, but can’t because he in prison.
While Michaela and Dixon are having a chat in his studio, Silver gives him a call. She knows that Michaela is still mad at her, so she asks Dixon to fix it, saying she has something else she needs to deal with. At home, Silver takes a call from an organizer of the Spencer Blane concert, for which Michaela had applied. The call is for Dixon, but Silver takes a message. She is told that Michaela has been chosen and isn’t too pleased to hear that. She tells the organizer that Michaela’s schedule wouldn’t allow her to participate in the concert and hangs up. At Annie’s, she returns home and learns that Liam is still really mad at her for writing the book. He says that his life is in disarray because of it and storms out. At Naomi’s, Jordan tells her that his mother is worried that he getting too close to Naomi will affect her (mother) reputation. Mark being arrested for narcotics possession has made matters worse. Naomi figures that because Jordan’s mother wants to keep Mark’s arrest under wraps, Mark could get released within a few days. Mark’s wife would then not come to know about the arrest and Mark can keep his kids from moving to Vermont with his ex-wife. Jordan points out that Mark will be in jail all weekend and won’t be able to attend his kid’s party, so his wife would come to know about his arrest. Naomi says that won’t be an issue because she will be throwing the party.
At Dixon’s, Silver tells Michaela that she has been chosen for the Spencer Blane concert, but can’t go on tour because she is carrying her baby. Dixon and Michaela both try to argue with her, saying this is a once in a lifetime opportunity. Silver doesn’t care and reminds Michaela that she has signed a contract with her. She tells Michaela that she will have to move back to Washington and cut all contact with Dixon because he is being a bad influence on her. Dixon is baffled as to who sent the song to the organizers. Michaela right concludes that Adrianna did it, to get back at Silver. At Annie’s, while she is busy going over the details of Mark’s case with Ms. Burns, Mark’s lawyer, Naomi convinces Liam to spend a day with Mark’s son, who is a big sci-fi fan. Naomi feels this would help Dylan, Mark’s son, forget the fact that his father isn’t around. At Adrianna’s, Dixon tells her about Michaela being chosen for the concert and about Silver’s reaction. Adrianna also feels this is a huge opportunity for both Michaela and him. She urges Dixon to not let Silver ruin it. At the birthday party, after Naomi has organized everything, she and Liam have talk about the fact that Mark won’t be there.
Liam thinks it isn’t a good idea for her to lie to the kids about why Mark won’t be at the party. She disagrees, saying some lies are good. The kids arrive with their mother and are really excited on seeing the grand arrangements. Before leaving, Mark’s ex-wife tells Naomi to ask Mark to drop the kids back home by 6 in the evening. Naomi assures her that it will be done. Dixon accompanies Silver and Michaela to the doctor’s. On the way, he tries to reason with Silver, but to no avail. She makes it clear that all she cares about is the child Michaela is carrying and nothing else. At Silver’s, Adrianna comes searching for her and finds Navid there. He tells her Silver isn’t home and he is there assembling a crib for Silver's baby. While chatting, they both concede that they are really attracted to each other and begin making out on Silver’s bed before eventually having sex. At Annie’s, while she is having a talk about Mark’s case with Burns, Jordan’s sister Elizabeth arrives. She surprises Annie by telling her that her (Elizabeth) mother wants to help Jordan with Mark’s case, but Jordan turned down her offer and isn’t returning her calls. At the party, while Naomi goes to get the kids some ice-cream, the kids tells Liam that the party is fun, but seeing their dad is the only thing they want.
On hearing this, Liam decides to do something about it. Naomi returns and finds Liam and the kids missing. At Naomi’s, Annie confronts Jordan, who is there planning a surprise for when Naomi gets back. After she tells him what Elizabeth said, he tells Annie that his mother doesn’t do anything without expecting something in return. He feels taking his mother’s help would be like doing a deal with the devil. Annie is really desperate to save Mark, so she urges Jordan to let his mother help, saying she doesn’t care about the consequences. While at it, she gets a call informing her that Liam is with the kids at the prison. She arrives there and a while later, so does Naomi. They are all touched to see, how happy the kids are on seeing their father. At Silver’s, while Navid and Adrianna are busy cozying up in bed after making love, Michaela enters to have a talk with Silver. She is shocked to see the two of them and quickly leave. Adrianna rushes after her and explains that she didn’t tell her anything because she didn’t want to hurt her. Michaela sees sense in what Adrianna is saying. At Naomi’s, she reprimands Liam and even slaps him in anger for what he did, saying Mark might lose custody of his kids once his ex-wife comes to know he is in prison.
At the hearing, thanks to help from Jordan’s mother, the judge rules that Mark is free to go. At the restaurant, Mark and Naomi bid each other a tearful goodbye because Mark has to move to Vermont, so he can be close to his kids. At his surfboard store, Sydney comes to see Liam. She tells him that she has left her husband and doesn’t care about the money anymore. She wants to restart things with Liam and asks if he is interested. Dixon tells Silver that he showed the contract that she has with Michaela to Mark’s lawyer. The lawyer told him that Michaela can do whatever she wants till she has proper medical care. Dixon tells Silver that she can’t legally stop Michaela from taking part in the concert. At Naomi’s, Jordan and Naomi are about to make love, when he gets a call from his sister. She reminds him that his mother helped him and now he owes her one. She wants Jordan to leave his girlfriend and immediately take the next flight to NY. Jordan reluctantly complies, but doesn’t tell Naomi the real reason before leaving. At Annie’s, she is shocked, when told by Liam that he wants to move to Australia with Sydney and start things over. He asks Annie to buy his bar, so he can do that. At Dixon’s, Silver and he return and are shocked to learn that Michaela has packed all her stuff and left. The episode ends at this point.
- Shenae Grimes as Annie Wilson
- Tristan Wilds as Dixon Wilson
- AnnaLynne McCord as Naomi Clark
- Jessica Stroup as Erin Silver
- Michael Steger as Navid Shirazi
- Jessica Lowndes as Adrianna Tate-Duncan
- Matt Lanter as Liam Court
- Keke Palmer as Elizabeth
- Amy Lawhorn as Dana Holland
- Jordan Austin Smith as Dylan Holland
- Chandler Kinney as Olivia Holland
- Melissa Ordwayas Sydney Price
- Naomi – Okay, Annie was a hooker and my rap sheet was a mile long. We still love you
- Adrianna – At some point you're gonna have to stop trying to make everyone else happy because Silver's only trying to make herself happy
- Naomi – Liam some lies are good lies, that's what families do
- Silver – Naomi says jump, we hop a plane across the country
- Naomi – Oh Annie it's so cute that you're keeping your sense of humor during this family tragedy you created
- Annie – I know it sounds really cliché, but telling the truth finally set me free of it all
- Liam – Look you're hot and all, but I'm exhausted so hop back on your mommy porn tour bus and get a real life
- When It's Over by Wild Belle
- Hunger by Rhye
- Old Friend by Sea Wolf
- Go Slow by Haim
- I Have Made Mistakes by The Oh Hellos