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If you liked Princess Princess add

...then you might like Back Street Girls: Gokudolls add

A trio of males are forced to act (or become) girls in order to appeal to a largely male fanbase. One of them is aimed more towards men, the other towards girls however. There is a lot more dark humour in Gokudolls and it is a lot more violent too, but the comedy is quite similar from the perspective of the three main characters.

If you liked Kuttsukiboshi add

...then you might like Fragtime add

Both are Shoujo Ai Both have an element of sci-fi / supernatural Fragtime is tamer than Kuttsukiboshi, but the latter isn't hentai. If you like short OVA / films with yuri and super powers (for lack of a better term) I would recommend either of them.

If you liked Love Hina add

...then you might like Tachibanakan Triangle add

This is basically what would happen if Love Hina had a female protagonist. There's a bit more Ecchi in Tachibanakan Triangle, but it captures the feel of both, Love Hina is definitely better romance / story-wise though, TT is purely slapstick comedy with ecchi thrown in.

If you liked Tenshi no Drop add

...then you might like Docchi mo Maid add

Both are 1 episode OVAs which revolve around a group of girls, both are fantasy and have yuri in them (Docchi Mo Maid more so) - the set up is very bizarre and isn't supposed to be taken seriously at all, Tenshi no Drop is the weirder of the two.

If you liked Chobits add

...then you might like Rizelmine add

Both are early 2000s Romantic Sci-fi anime with a little Ecchi thrown in. The main male protagonists are 4 years apart in age (Iwata is 15, Hideki is 18 - 19). The females are also 4 years apart (Rizel is 12, Chi is 16) Differences Chobits is considerably more dramatic than Rizelmine Rizelmine is a Lolicon series Rizel is a human with machine features, Chi is a complete machine capable of human emotions.

If you liked Les Misérables: Shoujo Cosette add

...then you might like Romeo x Juliet add

Both are based on works of fiction produced a few centuries ago. Both are Drama and Shoujo Both have Romance They are (or at least the original source material for Romeo + Juliet) are set in Europe. Both have had various adaptations of films, books, plays. etc One has Fantasy as an extra genre, although the original play, does not.

If you liked Kodomo no Jikan (TV) add

...then you might like Mitsudomoe add

both have a new teacher, in his mid 20s at best and a virgin, Mitsudomoe is funny all around where as Konoji has drama and romance Both are ecchi, but Mitsudomoe is visual gags, where as Konoji is panty's bras etc

If you liked Iketeru Futari add

...then you might like Colorful add

Both are 6 minutes long with a total length of 16 epsiodes, Both focus on Comedy and Ecchi very heavily, In my opinion more so in Iketeru Futari, they also have an extra genre, In Colorful it's School, in Iketeru Futari it's Romance. Both have quite large casts, although the episodes in Colorful have segments, Iketeru Futari usually revolves around the 2 main characters.

If you liked Junjou Romantica add

...then you might like 30-sai no Hoken Taiiku add

Both have to do with at least 1 character's first relationships Although one is heterosexual and the other is homosexual, there are shounen-ai hints in both, more in Junjou. Both seem to be romantic comedies. Believe it or not both have censored versions (more in 30-sai) Junjou is aimed towards homosexual men while 30-sai is aimed towards heterosexual men

If you liked Chobits add

...then you might like Suki na Mono wa Suki Dakara Shou ga Nai!! add

Romance, Comedy, the odd Ecchi moments, although in Sukisho it is "male ecchi" and in Chobits it is "female ecchi", Drama is amplified a lot during the second halves of the series 1 or more characters in both have alternate forms / personalities in order to help them find their love. both involve "psychological experiments" in some shape or form

If you liked Hanaukyou Maid-tai add

...then you might like Ladies versus Butlers! add

there is a lot of Ecchi and Harem in both of these anime, some of the episodes, by some i mean all, tend to go over the top with the ecchiness. Maids seems to be a popular theme with the 2 anime, it also explores the many criticisms over the Maid / Butler X Master / Lady relationship

If you liked Chobits add

...then you might like Hand Maid May add

Both involve a robot girl with a rather perverted on switch, the main theme is the male character is trying to win over other girls but because of a modern society issue, the robot and male character are laughed upon. Chobits features more drama the whole way through while Hand Maid May focuses on Harem moments, both are Ecchi and some Harem is involved in both but more dominant in Hand Maid May. I don't mind which you watch first, but both are very good!