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If you liked Maison Ikkoku add

...then you might like Bokura wa Minna Kawai-sou add

Male character fighting for a girls love while living in the same dorm (communal apartment house in Maison Ikkoku). The girls family owns the place so she has strings she can pull. The main character also shares a room with a strange man who is constantly invading his personal space. (In Maison Ikkoku, Mr. Yoshida lives in a separate room, but makes his way in through a hole in the wall constantly.) Both shows also have a risque, yet sensitive girl for a tenant.

If you liked Ima, Soko ni Iru Boku add

...then you might like Kaiba add

These shows are both set in distopian sci-fi settings. Although Kaiba's world is more blatantly smybolic and dreamlike, short, addicting, atmospheric, depressing, and downright harsh. Both are incredible and I recommend you watch them in succession for full effect.

If you liked Hentai Ouji to Warawanai Neko. add

...then you might like Outbreak Company add

Similar episode structure, between one light hearted otaku character (or in Stony Cat's case, a pervert), and two moe love interests (both have a dominatrix loli character that is upset at the fact that the other female lead is always in the way). Things eventually get surprisingly serious, and the main character makes heavy developments beyond his simplistic and comedic introduction.

If you liked Mugen no Ryvius add

...then you might like Kokoro Connect add

Kokoro Connect and Infinite Ryvius are both similar in that they amplify the angst and drama of youth. Things are very emotional, and taken very seriously (although both shows also have a good sense of humor and plenty of romance, which is where half of the emotion stems from). If you loved one of these shows for this reason, you will likely love the other one. I gave them both 9's, so personally I think they both are phenomenal.

If you liked Arakawa Under the Bridge add

...then you might like Mawaru Penguindrum add

While completely different, Mawaru Penguindrum occasionally has a similar tone to the humor. There is also a very strong Shaft quality to Penguindrum. Both are highly enjoyable, and I recommend them both.

If you liked Planetes add

...then you might like NHK ni Youkoso! add

I can't tell you that these shows are similar, because they aren't. But after watching Planetes, then NHK, I can say that I got the same feeling I got while watching Planetes. In the end they were both highly enjoyable, and overall both were top notch.