It was the sixth-season finale, and Charlie's ex-girlfriend, Mia, suddenly shows up, causing Charlie to re-think his relationship with Chelsea. Meanwhile, Alan, Charlie and Herb go to the hospital with Judith when her water breaks.
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Alan and Chelsea were becoming very close and were spending lots of time together. Charlie realized that this could work to his advantage, and he spent time doing his own thing while Alan kept Chelsea happy.
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Charlie struggled with how he felt about having Chelsea move in, and Alan felt that he was being forced out to make room for her.
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Alan lets Chelsea arrange a blind date for him and her new friend, not knowing the friend is Rose (Melanie Lynskey).
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Chelsea and Evelyn meet for the first time, and they want to get to know each other and build a relationship. Charlie didn't like this at all, so he tries to keep them from spending time together.
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Charlie released stress by having a drunken male-bonding night with the guys after Chelsea became angry with him when she discovered topless photos of an ex-girlfriend on his cell phone.
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When Chelsea became sick, Charlie decided to let her stay at his place so he could take care of her. Charlie tried very hard to not run away from Chelsea and her illness after she became demanding with her many requests.
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Charlie professed his love for his girlfriend Chelsea, but he wasn't ready for the response he received. This response made him do something very out of character that no one expected.
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Charlie realizes he has a big problem when he learns that his girlfriend is on her way over to his house, and he needs help from Alan and Jake to remove a half-naked woman from his bed.
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Charlie ends up in couples counseling after his current girlfriend becomes very dissatisfied with their relationship.
While they were in bed, Charlie's current girl of the moment, Chelsea, suddenly began crying after Charlie asked her if she wanted pudding. She wasn't' really crying about the pudding, but that's what set her off. She revealed to Charlie that she was sick of their routine, which consisted of TV, sex, and food. She said, "We don't go anywhere, we don't do anything. I want to know who you are; I want you to know who I am." Charlie thought they did know each other. Chelsea asked him what her middle name was, and he guessed wrong. He also had no clue what her cat's name was when she asked him. She knew his middle name, which was Francis. He called her a show-off.
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In this episode, Alan's receptionist, Melissa, didn't think that Alan's family appreciated him, so she asked him to move in with her and her mom.
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Judith is five months pregnant and Alan is convinced he's the father. Jake is in a bad mood, and Charlie is determined to figure out what's the cause of his sour spirits.
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In this episode, Alan tried to fight off the attraction that was developing between him and his receptionist, while Charlie and Jake competed with each other to win the affection of a waitress.
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When Charlie's old friend Andy, a womanizer like Charlie, suddenly died, it made Charlie take a look at his own lifestyle and he attempted to make a few changes in his life.
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Evelyn offered to pay for Jake's college education and planned to get Jake a car if he did well in school. Since Evelyn intended to take such good care of Jake, Alan considered taking an early retirement. Meanwhile, Alan and Charlie tried to figure out why their mother was being so generous.
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When Jake disappeared with the daughter of Charlie's new neighbor, a former NFL player, Charlie had to try to cover for him when her father came to Charlie's house looking for her. Meanwhile, Alan was able to get a hot date with the help of Charlie's Mercedes, but things didn't go so well.
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Charlie's new girlfriend wanted him to spend the night at her place. Charlie realized that he was very set in his ways, and he struggled with spending the night in a strange house. Alan attempted to punish Jake for getting kicked off the bus for mooning the girls track team.
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In the last episode, Alan really wanted Judith, but this week he wanted his space from her because she was being too needy and clingy. Herb still wanted to spend time with Charlie so Charlie could help him meet women while he and Judith were having their problems. While all of this was going on, Jake thought everyone wanted to send him to military school.<
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Alan became very excited when he found out that Judith and Herb were having marital problems. He was even happier when he learned that Judith kicked Herb out of the house. Alan couldn't resist the urge to attempt to get Judith to take him back and give him another chance.
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Charlie appears to have a conscience when he actually feels bad about the way he treated Jake's former 5th grade teacher, who became a stripper after she dated him. Charlie wants to help her out, but things take a turn for the worse after she has a religious conversion.
The first scene shows Alan, Charlie, and Jake at the drug store. They are there to get Jake a jock strap for gym class. Jake wasn't wearing one to class because he says it felt like he was flossing his butt crack. Charlie says to think of it as a "bra for your balls." All of a sudden, Jake's former 5th grade teacher, Miss Pasternak, bumps into the guys ...
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Charlie's relationships with women have rarely been approved by those closest to him. In this week's episode, Alan didn't approve of Charlie's relationship with his receptionist from the start, and he had a really bad feeling about the outcome. Alan tried to prevent Charlie from seeing his receptionist, but of course Charlie didn't listen.
Alan's car was having engine problems, so Alan woke Charlie up early so he would take him to work. They were sitting in traffic, and Charlie still looked like he was half asleep. "It's 7 o'clock, where are all these damn people going?" Charlie asked Alan.
Charlie then found out from Alan that Alan would also need a ride home from work. At first Charlie refused. "Take the bus" he said. Alan replied, "Charlie, it's only for a couple of days." Charlie then said, "That's what mom said when she brought you home from the hospital ..."
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It's a series of firsts for the guys as Charlie attempts cooking, Alan tries dating two women at the same time, and Jake takes a swig of beer. Katie: Bridget Flanery. Angela: Helena Mattsson. Stephanie: Nikita Ager.
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Alan loans Charlie money, but takes things a step too far when he tries to get the cash back. Herb: Ryan Stiles. Ginger: Lisa Jay.
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In the sixth-season opener, Charlie runs into an ex-girlfriend (Rena Sofer) whose son bears a striking resemblance to him. Russell: Martin Mull. Chuck: Aaron Refvem. Brenda: Meeghan Holaway. Clive: Brendan Patrick Connor.
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