Charlie encounters an ex whose son looks an awful lot like him.
Alan lends Charlie money and crosses a line in his attempts to get it back, resulting in Alan getting kicked out of Charlie's house and bunking at Judith and Herb's.
Charlie tries cooking, Alan tries dating two women at the same time and Jake tries beer. Chalie proves to be the sole success at his new endeavor.
Charlie romances Alan's sweet receptionist despite Alan's best efforts to prevent it. When Charlie breaks up with her, Alan must raise her salary and give her health benefits to get her to stay on as his receptionist.
The guys bump into Jake's former teacher who became a stripper after a fling with Charlie. Charlie tries to help her out by giving her a room and a job, but things spiral out of control.
When Judith kicks Herb to the curb, Alan comes knocking, encouraged by the fact that maybe it wasn't his fault his marriage ended. Meanwhile, Herb gloms onto Charlie in order to meet women but isn't quite in the same class.
Alan tries to escape Judith's grasp as Charlie and Herb go on the prowl. But Herb backs out and goes back to Judith. Meanwhile, Charlie and Alan threaten Jake with military school and find it's a surprising motivational tool.
Charlie's new girlfriend asks him to spend the night at her place, while Alan tries to enforce a punishment on Jake.
Jake disappears with the daughter of Charlie's neighbor, a former NFL player, and Charlie is left to cover his back. Meanwhile, Alan scores a hot date with the help of Charlie's Mercedes.
Evelyn offers to pay for Jake's college education, leaving Alan to wonder if he ever needs to work again.
One of Charlie's old partners in crime dies, leaving Charlie to reevaluate his own reckless lifestyle.
Charlie and Jake fight for the affections of a waitress, while Alan fights sexual tension with his receptionist.
Judith is pregnant with a baby girl and Alan is convinced that he is the father. Meanwhile, Jake is in a contentious mood and Charlie thinks he knows why.
Convinced that Alan's family doesn't fully appreciate him, Melissa invites Alan to live with her and her mom.
Charlie finds himself in couples counseling.
While Chelsea is out of town, a former girlfriend shows up drunk at Charlie's, but when Chelsea gets back early, Charlie must get the half-naked woman out of his room before Chelsea sees her.
Charlie tells Chelsea that he loves her, but instead of returning the sentiment, she just thanks him causing Charlie to worry about the balance of power in the relationship.
When Chelsea gets sick and Charlie has to take care of her, he must also fight the overwhelming urge to flee.
Charlie joins Alan, Herb and his next door neighbor in a night of alcohol-fueled sexual reminiscences after Chelsea finds nude pictures of another woman on his phone.
Evelyn finally meets Chelsea and Charlie, and tries to prevent them from becoming friends.
Chelsea sets Alan up on a blind date with her new friend, Rose. Alan actually hooks up with Rose, but Charlie is worried about her real intentions.
Charlie reluctantly agrees to let Chelsea move in as he mourns the loss of his bachelor pad. Meanwhile, Alan finds that there's not much space left for him in the house.
Alan and Chelsea become best buds, and Charlie decides to take advantage of the situation.
Charlie starts to question his relationship with Chelsea when he hears that Mia is back in town. Meanwhile, Judith goes into labor and Charlie, Alan and Herb rush her to the hospital.
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