Two And A Half Men: 10 Times The Show Broke Our Hearts

You don’t think of Two and a Half Men when you want a show that will make you feel sad. The show became a mockery of what it used to by its end, and all the heartbreaking moments dried up in favor of cheap jokes. 

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However, this only makes the earlier moments where the show was at its best stand out more, along with bringing the moments that signaled the series’ dip from quality in more of a stark light. We’re sure you’re still wondering when Two and a Half Men was so serious, so here are 10 times the show broke our hearts for you to see for yourself.

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10 Alan Undergoing Lab Testing For Money

You can’t fault Alan for being such a cheapskate considering he had to shell out more than $4,000 a month just for alimony, and the poor guy had to dig deep into desperation to earn that amount.

We saw the worst of this in one episode, where Alan was shown undergoing lab testing of various kinds just so he had money to pay for his alimony and child support. It was played off for laughs, but seeing Alan undergo all those horrible side effects did break our heart for him to see the guy struggle so much.

9 Jake Stops Talking To Alan

Jake is a complete dummy, so it becomes a big deal when he starts taking things seriously. In Season 8, Jake was at his angriest when he found out Alan was having a secret relationship with Jake’s best friend’s mother. 

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It was around this time that Jake stopped visiting Alan completely out of anger and refused to speak to his father. The surprise and hurt in Alan’s face were enough to make us feel sorry for him for being cut off from his own son’s life. It was the first time in a while that Two and a Half Men had felt very real.

8 Charlie Reflects On His Life

In one episode, Charlie’s visiting friend died after a lifetime of drinking and debauchery; this caused Charlie to rethink his own life. The show did a good job at getting around this too, as Charlie imagined his own funeral where he was disrespected by every attendee. 

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Those who know of Charlie Sheen’s exploits will have understood this was a kind of representation of how the actor must have felt in real life too, and it went a good way in humanizing the character who had been deep into his antics for quite a while by that point.

7 Charlie And Chelsea's Final Interaction

The entirety of Season 6 and Season 7 detailed the beginning, blossoming, and falling out of Charlie and Chelsea’s relationship. By its end, it was a shame seeing these two break up for good, as Chelsea had changed Charlie so much.

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Before Season 8 started, the hope was that Chelsea would return like so many of Charlie’s other love interests had, but their final interaction turned out to be definitive. The sad part is that both of them looked heartbroken for their relationship to be over, and there wasn’t anything particularly funny about it.

6 Charlie's First Death

Maybe Chuck Lorre thought he could get the fanbase to stop caring about Charlie Harper’s character by making a total mockery of him, but fans never got onboard with the revamp of Two and a Half Men.

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Even though Charlie Sheen was fired, fans had a liking toward his character on the show and to see his ashes being scattered around, while everyone present consistently joked about how horrible was, was not the farewell we wanted. It ended up being a sad episode rather than a funny one.

5 Charlie's Second Death

Again, Chuck just didn’t let go of his anger toward Sheen to give us a proper finale, and Two and a Half Men ended with Charlie Harper flattened by a piano. It would have been so much better to give us a heartfelt goodbye rather than a total fiasco that the finale was, and the sight of Charlie Harper’s death was just sad.

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Four years since that finale, fans generally feel it’s a shame that the character went out the way he did. After all, they could have made it better by having an off-screen departure, but in-universe Charlie Harper was crushed to death, making this a very gruesome fact.

4 When Walden Threw His Ring In The Ocean

Like it was before, Alan was again down and out with his finances and needed something big to bail him out. Walden, being a millionaire, had in possession Bridget’s ring that was worth an eye-popping amount, which Alan attempted to pawn off.

When he couldn’t bring himself up to do it and returned it to Walden, the latter threw it in the ocean. Alan’s plight was very clear as we saw in his face all the money he could have had to bail himself out of his problems. You can’t help but feel for him at the “So close, yet so far” aspect of this situation.

3 When Jake "Grew Up"

Let’s be honest and admit none of us wanted to see Jake get all those grown-up storylines Alan and Charlie had. So, when the show did evolve into giving Jake adult-oriented angles, the fans were sad to see the little boy having grown up in a bad way.

This first happened in the Season 8 premiere, where we saw two girls escape from Jake’s room in the morning, having clearly spent the night there. By the episode’s end, there was confirmation that Jake really had been up to some adult stuff, which made us all sad that now he too was becoming like Charlie and that the innocence was gone.

2 Alan And Judith's Divorce Confirmation

In earlier days, Two and a Half Men had a lot of heart in it, and the best moment of this was when Jake consoled Alan for his divorce. Here, Charlie made Jake understand that Alan was hurting inside and that he was putting up a brave face for Jake’s sake, which got Jake to appreciate his father.

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It was both heartwarming and shattering to see Jake approach Alan for an impromptu hug, as it was made aware to the viewer that Alan could never be with his son completely now that Judith had brought him to his lowest point.

1 Every Time Charlie Admitted He Loved Alan

Yes, this should be heartwarming rather than sad, but we know that all of these brotherly scenes meant nothing in the overall context of the show. The times where Charlie begrudgingly admitted he loved Alan were the best parts of the series; however, in the end, their impact was negated.

The final episode of the series even had Alan worry that Charlie was alive and prefer him to be dead, which makes it clear that those brotherly times were there just for the sake of the episode rather than having weight on the show’s canon.

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