If you liked
Suzumiya Haruhi no Yuuutsu
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...then you might like
Yahari Ore no Seishun Love Comedy wa Machigatteiru.
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Both have a cynical, pessimistic high-school guy as the narrator who has to deal with a lot of hectic occurrences involving those around him. He is in a club that is supposedly aimed to help others. That guy does progress throughout the series and learns some lessons along the way. The side characters in both shows are fun, colorful and lively. Their interactions with one another made me smile at times. Something notable about both clubs in both series is that the other members are constantly trying to cheer the main guy up. I hesitate to call either a harem but the main guy does receive a lot of love and attention from different characters in both. Both shows also have a pleasant soundtrack, consisting of a lot of piano and soft, upbeat orchestrated pieces. I personally like Haruhi much better, as I found the situations and characters more amusing (not to mention that haruhi's directing and animation makes the latter look disappointing) but Oregairu did have some merit to it, specifically with Hachiman himself. Oregairu feels like a laid back version of Haruhi when it comes to the interactions aspect, so if you have seen one give the other a try for sure.
If you liked
Mahoromatic: Automatic Maiden
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...then you might like
Kobayashi-san Chi no Maid Dragon
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Both have a cute, over-powered non-human maid who is deeply devoted and in love with their master. They are also both slice of life with some drama sprinkled in. Both deal with the theme of running out of time to spend with your loved ones. Most importantly, both have ecchi humor ;) I prefer Kobayashi's Dragon Maid, but they both have very sweet moments.