Out for coffee with Alan and Jake, Charlie bumps in to a woman he had dated about nine years prior, and before going up to her, he notices an 8-year-old boy with her. The boy looks exactly like Charlie... more
On his way out for the night Charlie realizes he's out of tip money and asks Alan how much cash he has on him. Alan has $38 which Charlie basically begs to borrow. Ever the tightwad, Alan wakes Charlie... more
Alan starts dating two women at the same time, and things initially work out without a hitch. Alan dismisses Charlie’s advice that things could get complicated, and that he should have lies ready just... more
Alan turns to Charlie for a ride to work when his car is in the shop, leading Charlie to meet Alan's attractive receptionist. Charlie pursues the young woman, Melissa, and much to Alan's chagrin she agrees... more
Alan and Charlie bump in to Desiree Pasternak, Jake’s 5th grade teacher, who Charlie had seduced years before. After Charlie dumped her she went off the deep end, losing not only her sanity, but her... more
After Judith asks Alan to take care Jake for three straight months, Alan and Charlie discover it’s because she and Herb are having marital problems. Later, Herb comes over to drop some things off for... more
After sleeping with Judith when she and Herb separated, Alan decides he can't rush in to anything serious with her again and meets her for dinner to make that clear. However, desperate not to end up an... more
After dating for about a month, Charlie’s new girlfriend, Chelsea, asks him to spend a night at her house and Charlie begrudgingly agrees. A creature of his ways, Charlie tries his best to settle in... more
After hearing that Alan has to go to Beverly Hills to check on Evelyn’s house, Charlie enlists Alan to take his Mercedes to the dealership, which is in the same part of town. Once there, Alan ends up... more
Evelyn invites Charlie, Alan and Jake over for dinner to announce that she has set aside enough money to pay for Jake’s college education, and as motivation, enough to buy him a car as well. Shocked... more
When Charlie’s good friend Andy dies prematurely, Charlie feels that his time on earth may be drawing to a close as well. Not only does he rush off to the doctor to get a complete check out, he also... more
When Alan and his assistant, Melissa, share a few kisses at his office Alan puts a stop to it right away, insisting that they keep things professional. Once back at home Alan can’t stop obsessing over... more
Alan has completely convinced himself that it was he, and not Herb, who conceived a child with Judith, and when he finds out that they have begun renovating a room for their expected baby daughter, he... more
Alan’s girlfriend, Melissa, throws him a surprise 40th birthday party which goes horribly. During the party Berta, Charlie, Evelyn and Jake ridicule and belittle Alan so incessantly that Melissa insists... more
Charlie and Chelsea are still dating but have fallen in to a bit of a rut, prompting Chelsea to end the relationship after one too many nights staying in, watching TV and eating Chinese take out. Charlie... more
Charlie’s girlfriend Chelsea has to go away to her Ex-Mother-in-law’s funeral, and Charlie begins to experience some jealousy when he discovers she will be staying with her ex-husband. The night Chelsea... more
When Charlie tells Chelsea that he loves her, she replies with a simple "thank you." Not used to putting his feelings out there and not having them be reciprocated, Charlie goes to Dr. Freeman to talk... more
When Charlie’s girlfriend Chelsea comes down with the flu, his natural reaction is to send her home so he can avoid getting sick. However, trying to prove how much he loves her, Charlie asks Chelsea... more
When Chelsea discovers some topless photos of an ex-girlfriend on Charlie’s cell phone, she storms off after breaking up with him. Meanwhile, Herb and Alan are both dealing with relationship problems... more
Chelsea and Evelyn meet for the first time, and Chelsea discovers that Charlie hasn’t told Evelyn about their engagement. In order to make this up to her, Chelsea starts spending time with Evelyn and... more
When Alan becomes a little too obsessed with building model cars, Chelsea insists that she and Charlie set him up with one of her girlfriends. She sets up a double date, and when Charlie and Alan show... more
Chelsea and Charlie get into a huge fight after the lease on her apartment ends and she suggests she move in to his place, even though he still wants his own space. After some soul searching and a chat... more
Charlie and Chelsea are on their way out for the night and Chelsea notices that Alan has sunken to an all time low, he’s brought out his ventriloquist doll. She invites Alan along and Charlie hesitantly... more
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, on the sixth season... more