Alan has been hiding the fact that he is dating Jake's best friend's mother, and when Jake finds out he decides to move back in with his mom.
Lindsey asks Alan to move in with her and Charlie is beside himself convinving Alan to say "yes".
Alan makes the jump and moves in with Lyndsey, but secretly sees Melissa on the side at Charlie's house.
Alan, Lyndsey and her son move back in with Charlie after the fire Alan accidentally caused destroys Lyndsey's house.
Alan paints the town red while masquerading as Charlie sneaks off for some cosmetic surgery.
Charlie dates a slightly older woman, something that he is not used to and causes him some problems adjusting.
Charlie's girlfriend decides that she cannot handle his stalker, Rose.
Charlie and Alan try to set their mom up with Russell, their local pharmacist.
Berta's temporary replacement does such a good job that Charlie is enamored with her; Alan thinks Lyndsey's ex-husband is following him.
Charlie's old girlfriend Courtney shows up after three years in prison, and Charlie starts spending lots of money on her.
Alan's money woes causes him to look elsewhere for money to get a nice birthday gift for Lyndsey.
Charlie and Courtney break up, sending Charlie back to see his psychiatrist.
Charlie and Lyndsey's friendship grows and Alan becomes suspicious.
Charlie's becomes obsessed with the newly "married" Rose; Jake and Eldridge engage in stupid and dangerous stunts and film them in an attempt to make money.
Charlie and Rose continue their romantic liaisons; Alan's attempts to borrow money to expand his chiropractic business takes a surprising turn.
Charlie is tired of the short periods of time he can be with Rose and tries to convince her to go away with him; Alan battles with his conscience over scamming his family and friends in a Ponzi scheme and finds a way out from an unexpected source.