"Help Daddy Find His Toenail" - Season 5

Alan forbids Jake from going to a concert with his friend and his 17-year-old brother, but a defiant Jake sneaks out of the house anyway.

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Meanwhile, Charlie learns that Linda is being honored at a banquet but she has yet to ask him to go with her.

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When Charlie confronts Linda about it, she asks him to attend the banquet, which happens to be on the same night of Jake's concert.

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Evelyn offers Charlie a pill to calm his nerves but accidentally gives him a pill from the wrong bottle.

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Unfortunately, Charlie makes a fool of himself at the banquet and embarrasses Linda.

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Later, Alan catches Jake and Charlie sneaking back into the house via Jake's bedroom window.

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The next morning, Charlie's behavior at the banquet has made the newspaper, with a photo of himself making devil horns behind Linda as she accepts her award.

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Charlie goes to Linda's chambers to beg for forgiveness, but she breaks up with him.

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Afterwards, a sulking and depressed Charlie orders takeout, but his spirits lift when a pretty, young delivery girl is at the door.

"Putting Swim Fins On A Cat" - Season 5

Alan panics over the household finances because Charlie hasn't sold a jingle in a while. Looking for ways to cut back, he goes to Berta, who won't even consider taking a temporary pay cut.

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Judith is no help either, refusing when Alan asks if he can cut back on child support.

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Charlie tells Alan it's not a big deal; he shouldn't worry so much about money.

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Unable to sit back and let the cards fall where they may, Alan decides to enroll in a paid medical trial for a pharmaceutical company which results in him getting a rash and having his hair fall out.

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Meanwhile, Charlie meets Linda's four-year-old son Brendan and finds the best way to communicate with him is to sing him little songs. Charlie makes a CD of the songs for Brendan to listen to when he's away.

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Linda's ex-husband, who happens to be in the music business, hears the CD and offers Charlie an advance and wants to get it recorded. Charlie jumps at the chance--it looks like Alan's worries about money are over.

"City of Great Racks" - Season 5

Charlie and Linda (Ming Wen) are seriously dating, and it's only a matter of time before they consummate their relationship. While out on various dates with Linda, Charlie keeps thinking he sees Rose, or someone who closely resembles her with a different hairstyle.

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He becomes so obsessed with the idea that Rose is everywhere that it drives him back to the therapist's office.

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His therapist (Jane Lynch) tells him that he has feelings for Rose and that she represents an unconscious desire for him to retreat into to his juvenile relationships.

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Back then, Rose allowed him to be anything he wanted to be and still loved him the way he was. If he does nothing to resolve these issues, he's doomed to a lifetime of shallowness.

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Charlie jumps on a plane to find Rose in London.

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She's still crazy about him, and asks him to make a commitment to her. Unknown to Charlie, Rose's flat in London is filled with different color wigs, proving she was stalking Charlie in Los Angeles all along. Lucky for him, he comes to his senses and heads home on the next flight out.

"Dum Diddy Dum Diddy Doo" - Season 5

Tired of dating bimbos and being the oldest guy at the bar, Charlie goes on a blind date with a municipal court judge, Linda (guest star Ming Wen). She's an intelligent, attractive, age appropriate, single mother who is clearly way out of Charlie's league.

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Their first date goes horribly, as Charlie can't help but put his foot in his mouth, and the relationship appears to be over before it starts.

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After several attempts to get in touch with Linda, Charlie gets arrested while out on the town, and has to appear in front of a judge, who just happens to be Linda. Linda thinks Charlie's arrest was just a ploy to get to see her again and Charlie slyly goes along with that notion. She agrees to have dinner with him again as long as he stays out of trouble.

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At home, Jake wants nothing else but to be on the phone with his girlfriend. Whether he's at the dinner table, watching TV or in the car, he's got the handset glued to his ear.

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But when picking up Charlie from the jail, Alan finally cracks and throws the phone out the car window.

"Media Room Slash Dungeon" - Season 5

Charlie hesitantly goes to an event with Evelyn and is pleasantly surprised to discover that she's great company, as long as she's directing all her venom at everyone else.

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Not only is Charlie having a great time with his mother at the event, he's being exposed to a lot of wealthy hot woman.

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Alan gets wind of all the fun they've been having together and grows increasingly jealous.

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At the event Evelyn introduces Charlie to a charming woman with whom he hits it off. However, Charlie feels as if he must choose between spending time with Evelyn or this new lady.

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Of course, Charlie picks the woman over his mother, only to have the audience discover that Evelyn orchestrated the whole thing in order to have the husband find his cheating wife with Charlie. This would break up the marriage allowing Evelyn to sell their house.

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Charlie and Evelyn used each other to get what they wanted, and in this case, Evelyn outplayed him.

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Meanwhile, Alan begins dating a "damaged" woman who constantly weeps after sex. After seeing a therapist and getting back on her meds, Alan gives the woman another chance only to be faced with the same results.