Two and a Half Men has been making us laugh since 2003 all the way until the end of its twelfth season in 2015. In season 9, we’re introduced to the new leading man, Walden Schmidt (Ashton Kutcher). While this billionaire is sweet, humble, and totally relatable, we can’t deny that he’s done some things that definitely had us shaking our heads. Although he usually means well, he’s made some pretty questionable choices. Here are the 10 worst things Walden has ever done, ranked.
RELATED: 10 Guest Stars We Forgot Were On Two And A Half Men
10 When Walden Donates Charlie’s Piano
In the first season, in “Thank You for the Intercourse,” Walden decides to start clearing out Charlie’s things. He donates Charlie’s piano without asking Alan, which causes him severe distress since the object had so many emotional memories of his brother. Sure, Walden didn’t mean it, but don’t you think he should’ve known that something so special to Charlie also would’ve been special to his brother? He could have at least asked, right?
9 When Walden Pretends to be Poor to Sleep with a Cougar
In “Something My Gynecologist Said,” Walden takes Alan’s bike to get fixed. However, when it doesn’t fit in his car, he takes Alan’s. Of course, this not-so-great vehicle breaks down on the side of the road, and Walden is picked up by a rich older woman. Thinking that he is poverty-stricken, she invites him back to her place. Walden keeps up the ruse that he is poor, and even lets her buy him things. This is a pretty sketchy thing for a billionaire to do, even for sex. However, Walden does get his just deserts when he arrives at her house one night and finds another, even younger, man there.
RELATED: Two And A Half Men: The 10 Worst Things Charlie Has Ever Done, Ranked
8 When Walden Becomes More Interested in His Date’s Grandmother
In “Cows, Prepare to Be Tipped”, Walden goes out on a date with a young 22-year-old (Hilary Duff). Stacey is ditzy, and gets pretty drunk, and Walden ends up taking her home. However, he ends up becoming much more interested in her attractive and intelligent grandmother. No, we can’t even make this stuff up. What is probably the most sketchy and annoying about Walden is how he tries to hook up with all of these young women, but ends up swaying towards older women. Things would be much more simple if he could just make up his mind.
7 When Walden Pretends to Be Gay With Alan to Adopt a Child
Sure, we totally understand where Walden is coming from, and we’re not disputing that the system might make it difficult for single men who want to have a child. However, we’re not on board with using your best friend, having a fake wedding, lying to a social worker, and then still trying to sleep with unsuspecting moms on the side. There had to be a better way, right?
RELATED: Ranked: Two And A Half Men’s Funniest Characters
6 When Walden Makes Out With Jake’s Ex-Girlfriend
You know, we really thought that Walden was a pretty gentle and sweet man, but honestly, can he ever keep it in his pants? In “Bazinga! That’s From a TV Show,” Tammy and Jake break up. While Tammy may be much older than Jake (and pretty close to Walden’s age), they still dated for a long time, and Jake was pretty smitten by this woman. Sure, this is also probably one of Jake’s not-so-redeeming moments, as he is now dating Tammy’s younger daughter. So, this whole episode is kind of a total mess. However, we’re still going to venture to say that you shouldn’t make out with your best friend’s son’s ex-wife an hour after they break up? Gross.
5 When Walden Breaks Up With Kate (Again) On a Whim for Another Woman
In “Lan Mao Shi Zai Wuding Shang,” Kate finally returns from her travels, and the two sleep together and try to work it out. However, when Kate leaves for another trip, a hiker shows up on Walden’s deck. (We’ll just sidestep that this woman is actually Mila Kunis, Ashton’s boo in real life). He offers for Vivian to stay the night, but she leaves the next day. Of course, this is never enough for Walden, and he ends up breaking up with Kate and chasing after Vivian. Vivian ends up telling Walden that he falls in love too easily, and they part ways. Thank goodness for Vivian’s honesty, because jeez, Walden seriously needs to make up his mind.
RELATED: The 10 Worst Episodes Of Two And A Half Men (According To IMDB)
4 When Walden Asks Bridget to Sign the Divorce Papers In Bed
Yeah, you read that right. In “What a Lovely Landing Strip,” Bridget shows up to Walden’s house, and the two head upstairs to sleep together. A half-naked Walden goes to the bathroom to ask Alan for advice (remember, he’s also kind of seeing Zoey at this point,) and ends up returning to the bedroom to ask Bridget to sign the divorce papers. Furious, Bridget ends up driving her car into Walden’s house, which is pretty yikes, but like, we kind-of get it.
3 When Walden Makes Out With Judith
In the third episode of the ninth season, “Big Girls Don’t Throw Food,” literally right after we meet this seemingly lovable character, Judith pulls the moves on Walden after a deep talk. While this doesn’t really go anywhere, Jake of course videotapes it and blackmails his mother into letting him quit high school. While this wasn’t exactly initiated by Walden, it’s still not a great first impression to make out with your new roommate’s ex-wife.
RELATED: 10 Jokes From Two And A Half Men That Have Already Aged Poorly
2 When Walden Sleeps with Evelyn
If there’s one thing worse than sleeping with your friend’s ex, it’s sleeping with your friend’s mother. In the episode “Those Fancy Japanese Toilets,” Walden hires Evelyn as his interior designer. He is fairly warned by Alan, but it clearly isn’t enough to stop Evelyn from sinking her claws into the young billionaire. Not your finest moment, Walden, and we’re pretty sure you’ll never live this one down.
1 When Walden Lies (For a Long Time) To His Girlfriend
We’re all familiar with the alias, “Sam Wilson,” and this little charade goes on for a few episodes. We understand where Walden is coming from – he wants women to love him for who he is. However, he never thought through breaking the news to the woman when he realizes that he actually thinks she could be “the one.” Of course, when Walden tells Kate that he’s actually a billionaire, and his whole life is pretty much a lie, she isn’t exactly super pleased. While his intentions were good, they’re actually pretty selfish, and of course that woman is going to be super unimpressed. We saw that coming a mile away, Walden.
NEXT: Funny Sitcoms Like Two And A Half Men