7 Epic relationship fails of Alan Harper from Two and a Half Men

Chuck Lorre’s Two and a Half Men premiered in 2003 and followed the lives of two brothers, Charlie (Charlie Sheen) and Alan Harper (Jon Cryer), and Alan’s son, Jake (Angus T. Jones). As Alan’s divorce from Judith is almost confirmed, he moves into his brother Charlie’s home with his son Jake, disrupting Charlie's self-indulgent way of living.

While trying to raise his son, Jake, Alan also indulged in many relationships, like his brother, most of which ended terribly. From his marriages, short-term relationships to long-term relationships, Alan has failed over and over again due to several reasons, such as cheating and being dumped, among others. Here’s a list of 7 such relationship fails of Alan Harper from Two and a Half Men.

Disclaimer: The article is based on the writer's opinion. Reader discretion is advised.

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7 Epic relationship fails of Alan Harper from Two and a Half Men

7) Naomi leaves Alan for Hector

Introduced in Season 4 of Two and a Half Men, Naomi is Charlie’s housekeeper and Berta’s daughter. Naomi had lost her job after getting pregnant and also for stealing computers and a Xerox machine from her office.

She secretly dated Alan for a short while after giving birth. However, her mother still finds out but doesn’t stop her, as Alan was the best out of all the men she had previously dated. But the secret relationship still ends after Naomi chooses her baby’s father, Hector, over Alan, adding another relationship failure to Alan’s list of failures.

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6) Jamie rejects both Charlie and Alan

In the Season 2 episode titled "A Lungful of Alan, we meet Jamie (Paget Brewster), a friend from the Harper brothers' childhood. Charlie used to make fun of her for being a little too chubby and called her ugly. However, the brothers are shocked to see her transformation as an adult.

Alan feels jealous of Charlie getting all the attention from Jamie, but it later turns out that she was only trying to take revenge on him for making fun of her as a child. Alan thinks the situation might give him a chance and tries to impress her, but she rejects him as well, telling him that as a child, she was interested in him, but not anymore.

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5) His failed relationship with Lyndsey McElroy

Alan’s relationship with Lyndsey was one of the longest relationships that he had had over the years. She began dating in Season 7 of Two and a Half Men but had to go through a series of failures in the relationship, ultimately breaking it up.

Alan, while in a relationship, cheats on Lyndsey with Melissa, and even Lyndsey cheats on Alan multiple times during their relationship. He later burns her house down, resulting in her and her son moving in with Alan and Jake in Charlie’s house. He also gives stolen jewelry from Judith as gifts to Lyndsey. Throughout their on-and-off relationship, Lyndsey broke up with or kicked him out of her house several times, resulting in another failed relationship for Alan.

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4) His relationship with Rose

Rose is a major recurring character from Two and a Half Men and is known for her dangerous stalking tendencies toward Charlie. However, in episode 21 of Season 6, Chelsea sets up a blind date for Rose, who turns out to be Alan. Surprisingly, they both like spending time with each other and began dating.

However, it turns horrifying when Rose begins showing her stalking tendencies toward Alan and gets clingy, just as Charlie had warned it would be. He later breaks up with her after she causes a painful accident for him.

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3) Marriage and divorce from Kandi

Kandi was introduced in Season 3 of Two and a Half Men and was initially Charlie’s girlfriend before she began dating Alan. They began dating and even got married later.

However, just like with Judith, Alan is thrown out of Kandi’s home as she files for divorce after four months of marriage. She later gets to keep the condo they bought and even receives alimony. Kandi was one of the few relationships where, even if it didn’t work out, they still remained good friends.

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2) Divorce from Judith

The story of Alan and Jake in Two and a Half Men begins with Alan getting a divorce from Judith, who kicks Alan out of his own house, and he has to go live with his brother Charlie.

She is revealed to be enjoying her single life after divorcing Alan. It is even revealed that her and Alan’s marriage was not a happy marriage, and they were not happy with each other, resulting in the divorce that was initiated by Judith.

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1) Alan and Melissa’s disastrous relationship and breakup

Melissa was introduced in Season 6 of Two and a Half Men and was in a relationship with Charlie before dating Alan. Their relationship was marred by cheating and lies, as Alan always ended up lying about himself.

For instance, she berates Alan for not having enough money and not having a house of his own. He joins his mother’s business to earn extra money and plans a date with Melissa in one of the empty houses and lies to her about renting it. The date ends horribly after Evelyn reaches the house with potential clients, and they have to run out of the house.

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