Don't Trust the B---- in Apartment 23

Chloe tells June that Benjamin is going to be in town to shoot a commercial with James. She is excited and has even moved him up to #1 in her guy rotation. June tells Chloe that she has to tell him about her rotation if she really likes him. June recounts her own story about being unaware that the guy she liked was dating another girl. Chloe tells Benjamin that she is dating five other guys, and is surprised when Benjamin tells her that he is also dating five other girls. They bond over this. However, after a they hook up in the bathroom and Benjamin slips and falls, Chloe takes him to the hospital but discovers that his emergency contact is a girl named Melinda, who is number one in his rotation. She is hurt that she is not his number one. June tells her that she understands what she is going through, for the first time Chloe is feeling jealous.

June discovers that Chloe has been attending Alcoholics Anonymous Meetings, to share her crazy partying stories as well as take free booze from the alcoholics. Pepper sets Mark up on a date with one of her friends, and June struggles to hide her jealousy. Chloe tells June that she is using Mark whether she realizes it or not, and toying with his emotions. Mark admits to June that he likes her but she is unsure if she feels the same. They decide to have sex, but the result is not what they expected- it is awful. Meanwhile, James learns that he is on the short list for Woody Allen’s film “Monte Carlo, Monte Carla” but he may not get the role because Woody does not think he is deep enough.

James invites Chloe and June out to dinner to meet the girl he has been dating, Emily. At the dinner, Chloe after barely talking to Emily says “Veto”, forcing James to break up with her. Chloe explains to June that she and James have veto power over who they each date. Chloe doesn’t want James to date anyone that will make him soft and complacent. However, she soon finds out that James has been secretly continuing to date Emily. Chloe decides that they need to take a break and end their relationship. But soon Luther and June realize that they must get the two back together after each of their lives begin to change- Chloe has begun working at a cell phone store, where she can fight with customers all day, and James has become fat, soft, and complacent.

June receives her 1 year roommate evaluation from Chloe, in which she is shocked to find that she has been given a D. She eventually realizes that the only aspect in her life that she could possibly be slacking off in is her love life. Luther sets her up with James’ agent’s assistant, Will. The two really hit it off and bond over having to deal with a crazy person in each of their lives. For June, it’s Chloe and for Will, it’s one of his clients, Chris Spalding, a demanding novelist. It is soon revealed that Chloe is Chris Spalding. After attempting to share this information with Will, June’s plan backfires and Chloe has Will fired. June turns to James, who desperately needs Will’s help on his own projects, to help get his job back. During this time, James is struggling to land an audition for a new Woody Allen film “Monte Carlo, Monte Carla.”.

June is startled when a man she has never seen before jumps out of a door in the apartment that she has never seen before. It is Teddy, Chloe’s childhood friend from Camp C.U.T.S. (Callous Unemotional Trait Survivors) who visits her every year when he goes off his medications. His visit coincides with the Carter Marsh Annual Warehouse Sale, where Chloe uses psycho and manic Teddy to her advantage against all the vicious out of town women at the sale. But this year, Chloe finds herself increasingly distracted by her relationship with Jonathan. Meanwhile, James is devastated when he finds out that his Beek Jeans have been relegated to the “cooling rack” at the sale where no one is buying them.

June has been so stressed and consumed with work that she has no time for anything else, including Chloe. Chloe's remedy for this is to slip June an herbal relaxant, but the next thing June knows, it's Tuesday and Monday is a complete blackout. As she tries to piece together what happened, June discovers some surprising things about herself. Meanwhile, James grapples with the idea that he may have impregnated June's friend, Crissy, on her wedding day.

After struggling to make ends meet, June comes up with a creative way to make extra money; little does she know, Chloe has plans to make extra money too, and her plans are a little less innocent. Meanwhile, James launches a line of super-skinny jeans.

June obtains not one but two jobs AND an internship; Chloe has a bad idea and June is left to pick up her mess; James lands a role opposite the child star from Mad Men.

June moves to Manhattan to follow her dream job and the most perfect apartment, but they both disappear in seconds after her arrival, thanks to a CEO from the Bernie Madoff School of Embezzlement. Without anywhere to live or work, June seems to turn her luck around when she gets hired at a coffee shop and meets Chloe, a charming, vivacious roommate without any morals. Chloe soon spends all of June savings, but she and her snarky friend, James Van Der Beek, come to learn that June is not as dumb as they thought. June turns the tables on Chloe, who is so shocked about it that she accepts June into her group of friends. June, with the help of her new friends, might just learn how to survive in New York City.