The longest running and highly successful sitcom Two And A Half Men is loved by fans all around the globe for its impeccable comic timing and hilariously raunchy and funny moments. Everyone loved to hate Alan, the brother of protagonist Charlie Harper, and it does seem that that's what the showrunners were aiming for!

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Alan has gone through the most unpredictable character arc throughout Two and a Half Men's entire run, transforming from unassuming loser to someone possibly worse than Charlie. And yet, there's a lot about him that just doesn't add up. Here are 10 things about Alan that don't make sense.

10 Why The Beach House?

When Judith divorced Alan, she got the house in the settlement. She immediately threw Alan out and naturally, Alan broke in to Charlie’s Malibu house. The twist is that Alan appeared with Jake by his side.

Was it a weekend when Judith asked him to leave? Why did she throw Jake out too, seeing it was the first time Alan was moving out? Also, Alan knew Charlie would be a corrupting influence on a then-growing Jake but he kept letting the two hang around, regardless. Why was Alan so into the Malibu beach house?

9 Did Alan Really Care For Jake?

After the tenth season, neither Alan nor anyone else mentions Jake twice, at least until the end of the series when Jake finally showed up with no explanations on his whereabouts.

Why did Alan not talk to Jake for two years? Why did he not file a report or look into Jake’s mysterious disappearance? Did Alan care for Jake at all, or did he just lose interest? It sure doesn’t look like it based on Seasons 11 and 12!

8 Why Didn't Alan Declare Bankruptcy?

From the start of the show, Alan was struggling to make money and it was shown several times that he was not making enough to get by. Despite this, Alan continued paying a huge alimony to Judith.

Not only that, Alan used to pay for all the expenditure pertaining to Jake’s studies or extra curricular activities. It is impossible to survive when one is not able to save even a penny for themselves, so why didn’t Alan file bankruptcy?

7 Will The Real Alan Harper Please Stand Up?

At the start of the show, Alan is a pretty decent man who is facing the brunt of a psycho wife and a highly dysfunctional family. He maintains this well-meaning if unlucky facade until he suddenly doesn’t.

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It’s as if Alan suddenly morphs into a blood sucking parasite who is shamelessly living off of others' efforts. He even tries to cheat Charlie, his friends and Berta in an elaborate Ponzi scheme. So who is the real Alan?

6 Alan & His Ladies

Throughout the twelve seasons, audiences saw Charlie, Walden or others making fun of Alan's low demand among women. This doesn't make sense because while Alan’s taste in women was incredibly bad, he has had more than a fair share of girlfriends. He was lucky not only in the number of dates he's had, but in his partners' looks. In fact, most of Alan’s girlfriends have been hot and pretty.

He even managed to marry Kandi, who went on to be the heartthrob of millions, including Walden. And yet, he is always taunted about being the opposite of a ladies' man!

5 Did He Have A Fake Retirement?

When Evelyn offers a generous amount to take care of Jake’s education, Alan feels liberated. With Judith already remarried and off the hook, Alan decides he doesn't need to earn any more and starts indulging in little extra curricular activities. He even picks up a new hobby of water surfing.

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Sadly, all of this lasts for just one episode because exactly one episode later, Alan is once again seen struggling to make money, pay bills, and scrape by. Moreover, this retirement escapade is never mentioned again.

4 Why Did Alan Start Living With Walden?

After Charlie’s exit, Evelyn sells his house to a young and handsome millionaire Walden (Ashton Kutcher). The weird thing is Alan manages to woo this man too and starts living with him in the same arrangement as before.

Things do not stop here, as Walden even starts treating him as a family member. Honestly, Alan has started to look more like a pest by this time! Which leads to the next question...

3 Why Didn't Walden Throw Alan Out?

Walden allowed Alan to stay in his house, which is weird in itself. What is extremely unsettling is that by the end of the series (i.e. around Season 10), Walden does not look very fond of Alan.

He seems creeped out  and even sometimes grossed out by Alan and yet, he never throws Alan out. Walden never asks him to leave or find some other arrangement, which would have saved him a lot of grief.

2 Why Did Alan Marry Walden?

In the final season, Walden expresses a desire to adopt a kid. However, the difficult adoption procedures do not allow him, a single man, to adopt a kid. To get around this, he marries Alan in a scam marriage.

This does not make any sense because the kid completely vanishes from the scene after a few episodes and no one talks about him ever again. Also, Walden and Alan divorce each other rather soon and start dating women again! So what happened to the kid? Who knows!

1 Why Does He Keep Paying Judith?

Judith wants out of the marriage because, apparently, she just found out her true sexual orientation and discovered that she is, in fact, a lesbian. The couple goes on to have a messy divorce with a much messier settlement. Charlie starts sleeping with Judith’s lawyer Laura and then one day abruptly breaks it off.

Furious, Laura successfully gets the court to give Alan's house, retirement funds, Jake's custody and pretty much everything else to Judith. Alan could have sued Judith's lawyer for malpractice and most probably win but instead, he keeps paying fat paychecks to Judith every month. What's up with that?

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