Maria†Holic

They share a similar setting and gender bending theme. Both of them excellent anime. 

Maria+Holic's lead is essentially a parody of OtoBoku's main character. The premise that causes them to do what they do is similar, but minus the sadism and arrogance in Maria+Holic's main character. 

Both anime' has a cross-dressing male character. 

both boys are in a girls school by the same reason, there´s flesbianism too  

also a guy disguise as a girl in a girl's school. though it's new i'm sure it will be a good way to continue with the boy beeing a girl in a girl's enviroment anime. 

Both of them tells about a boy who attending school at All-Girl school, and both of them was a beautiful wo(MEN). Please don't falling in love with her/him 

they both have a guy cross dressing but in otoboku(otome wa boku ni koishiteru) there is less yuri scenes than maria+holic. But in Maria+Holic there is multiple text screnes. Otoboku has a sense of seriousness  

Both has cross dressing boys that can pass off as female students, because some messed relatives wanted these boys going to an all girls catholic girl. Plus the boys can also be traps as well, b/c they completely fool the girls around them and only a few of them know their secrets.  

Both are about a blonde boy who is forced to cross dress and go to an all girls school by their grandparent. 

Both series are comedies done by SHAFT in similar styles. While Maria Holic has a more structured plot, it can be just as wacky as SZS. Maria Holic also parodies Nozomu's despair sequence from time to time, which SZS fans will love. I suspect that Dorm Mistress and Kafuka are related. They are eerily similar. 

- Made by SHAFT, and also share some voice actors; - Comedies with parody elements and a dark sense of humour; - School setting with a quite interesting and unique cast of characters; - Main characters are in despair; - Shoujo-ai hints/fanservice. SZS is funnier, longer and wackier. 

Both are Studio SHAFT productions under the helm of Akiyuki Shinbo, which rely on fast paced gags, puns, and innuendos. The style of comedy is similar, and some of the jokes cross over from Zetsubou-Sensei 

Both series have the same producers so there are elements which are similar between the two. The comedy and the art style are basically similar. 

It's been said and exhausted before, but both are fun, crack, series to watch when you're in the mood for a great comedy. Both Sayonara Zetsubou Sensei and Maria Holic do not have much continuity (Maria Holic has a slight bit more, but that's not saying much), great opening themes, and a great sense of humour. 

Beyond the obviousness of their both being Shaft productions, each has a single theme that gets beaten senseless. These one-trick ponies get lost in the wilderness and well before they actually finish, each runs out of things to say. Many episodes would have benefitted from losing 5-10 minutes since much of the repetition would have been cut. Losing a few episodes would have helped the series as there were a few too many in which nothing happened -- the season finales offending most egregiously. Typical for Shaft shows, the music is mostly interesting. The artwork is good and the characters are visually attractive. To sum the experience up... I feel like I've watched two comedy skits that were turned into feature films.  read more 

The artwork and the animation is pretty much the same. Maria Holic might be a little lighter than Sayonara Zetsubou Sensei, but there's numerous characters and lots of high school girls absurdities in both of them. 

Exact same director. Exact same visual style and jokes. 

Both are animated by shaft. Both are made with Akiyuki Shinbo's uniuqe directorical aproach. The humor in both anime is similar. Both MCs are despairing over something. Both premises are uniuqe and refreshing. 

Almost exact same plot where the main character is stuck with keeping a secret about the a cross dresser's secret[In Mayo Chiki it's a butler dressing girl and in MariaHolic it's a crossdressing rich boy]. They almost have the same feel but I'm finding Maria Holic funnier, while Mayo Chika plays all the ecchi out  

Both about crossdressing in a school with some sort of maid thing going on and an unwitting person accidentally getting stuck keeping that crossdressing a secret. 

Very identical, Think of Mayo Chiki as a Maria Holic but reversed, for example the lead charaters gets nosebleed/Hives from the opposite sex/Mariya and Subaru both crossdressing and the main characters fines out that they crossdress exc. Mayo Chiki is not as quirky and random as Maria Holic. MAyo Chiki adheres more to male perceptive like fan service exc. 

both have sadistic characters, both have butlers / maids 

Same basic plot, but gender inverted. (Well, to an extent. If Mayo Chiki was completely gender inverted there would be mass public outcry.) Both have gender bending shenanigans, and a lead that has a phobia of the opposite sex. Mayo Chiki is more ecchi, and Maria Holic takes itself a little less seriously. 

both animes about only girls schools and both are somehow related to maria-sama and kind of Religious! both are pretty nice and have kind of calm atmosphere though maria holic is funnier!! 

Maria+Holic is pretty much a parody of the Catholic girl's school life that Marimite portrays. 

Maria Holic is a parody of the entire shoujo yuri genre in all its floweriness, but especially of Maria-sama ga Miteru. The school in Maria-Holic is Lillian Jogakuen with the over-the-top prettiness pushed to the next degree. Several of the characters are similar. Even the soundtrack seems based on Marimite's at times. No one would like Maria Holic more than a real Marimite-holic. 

cross dressing school life. 

Both animes revolve around a high school where one of its students is crossdressing as a members of the opposite gender. Both are very funny and worth watching.  

It's almost a yuri-orientied version of Ouran High School.Both of them has crossdressers(Haruhi for Ouran and Mariya for Maria + Holic).While Ouran features Bishônens and yaoi-like scenes,Maria+Holic features Bishôjos and yuri-like scenes but has much more dark humor,unlike Ouran High School 

It’s a trap! PriPri is set in a all-male school and MH is set in a all-female school, but they have the same feel. Both are comedies and basically make fun of, respectively, the shounen-ai and shoujo-ai genres. Also, Yuujirou and Mariya are similar: pretty, blonde, popular, and quite sadistic boys. 

Crossdressing boys, room for slash, only diff is that Princess Princess is an all-boys school.  

You could call Princess Princess the brother anime to Maria Holic. The two anime involve crossdressing, are set in same-sex schools as well as having shounen ai and shoujo ai hints. Although both anime may have these hints there is actually nothing concrete from these genres, at most, a kiss. Maria Holic, set in an all girls Catholic school could be considered a 'black comedy' since the main character Maria, is known to be a sadistic cross-dressing boy who bullies the bonafide lesbian and focuses on the idea of homosexuality a lot more whereas Princess Princess is more of an all-round comedy that deals with the boys' problem of having to crossdress for the sake of the all boys school they attend. Neither shows are particulary groundbreaking, but they provide decent entertainment.  read more 

It's pretty much a mirrored version of Girls Bravo, with both main characters of each show being allergic to the opposite sex. 

Some of you guys are probably wondering how Maria Holic and Girls Bravo are related to each other. Well both of the main protagonist break out in hives when ever they come in contact with the opposite sex. Both kinda focus around a main character trying to build up a harem. Well that's pretty much all I got for this one. There's probably some better recommendations out there, but I tried. Thanks for reading. 

Same director. Kanako and Himeko are practical twins (besides the latter's superior silliness and - presumed - heterosexuality). Mariya might or might not be likened to a vicious and gender-swapped Becky. Matsurika channels Ichijou, down to even the deadpan eyes. Both animes make use of quirky Shindo-isms/SHAFT-isms (immediately recognizable to fans of the man and company). PPD is significantly more episodic, but both have unusual (crack!) humor.  

Self aware and self deprecating humor is relatively common, and both Mariaholic and Pani Poni share this trait. They have a cast of characters that are cliche to an extreme, and their ridiculous, fetishized personalities are constantly lampooned. There is also a certain random and outlandishness that defines these two series' as well. Episodes will often not even complain a discernible subplot, and scenes may shift to ridiculous mascot characters without warning. 

Both have a type of airy yuri theme to them with funny parts except that Maria Holic possesses a greater deal of character interaction. All in all, if you're looking for a cheery and hilarious yuri anime, try Maria Holic!  

Both female leads are extremely perverted and the school they go to is most to all girls,both are hilarious comedies and both don't follow a plot. 

Both main characters are extremely perverted lesbians. 

Even though both of these two animes have completely different atmospheres. I My Me! Strawberry eggs calming while Maria+Holic chaotic-like. They both have guys cross-dressing as girls attending schools where they have to keep their real genders secret. 

All Girls school... girl love, girl love, girl love. But i guess MariaHolic kinda isn't all girl love as the main character and love interest is a cross dressing boy....  

Similar character interactions: in both we have the bully (Haruhi/Mariya), the one being bullied (Mikuru/Kanako), and the silver-haired smart kuudere who just doesn't care (Yuki/Matsurika). Both anime are of the school, comedy and parody genre. 

kyoko's fantasies are similar to kanako's, both series are sparkly and contain excessive nosebleeds (maria holic tends to parody this trope though), both are set in a school (middle school for yuri yuri, high school for maria holic) both contain absurd humor.  

They both have the same kind of humor. In both series they build the story around a main character having extreme nosebleeds in everyday situations. The difference is that in Maria Holic the main character is attracted to girls, and in Yamato Nadeshiko Shichihenge she's attracted to boys. Both animes use a lot of overly dramatic dramatic effects and random events for comedy effect. If you like one of the series you'll probably like the other one as well!