 If you liked
Yahari Ore no Seishun Love Comedy wa Machigatteiru.
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 ...then you might like
White Album 2
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I heard these two compared and contrasted on a forum as something along the lines of "one is about three friends unselfishly seeking friendship and finding love; the other is about three friends selfishly seeking love and finding friendship". I'll let you decide how true that is after having watched it but I did feel these two were semi similar.
The biggest similarity is the dynamic of the three main characters, a male and two females (and the two girls are sort of parallels character wise), and the unspoken feelings between the three of them. I think Oregairu does an overall better job character and story
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Both have love triangle elements where a group of friends tries to balance their friendships and their feelings for each other. The female main characters are similar in both.
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Recommended by MisterTrantastic
Yukinoshita Yukino is like Kazusa Touma & Setsuna seems Yui. Kitahara & Hikki - both are inteligent, it seems they have same love-triangle problem & it becomes drama...
Love triangles, drama, high-school students. And I also got the strong oregairu vibe after finishing White Album 2 (spicier oregairu but isn't as spicy as School Days).
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Recommended by HollowLive_VOID
Smart main male protagonist, check.
Talented tsundere Black-haired female, check.
Bubbly pretty red/brown-haired other femla, check.
Feels, double check.
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Recommended by Microwaves
A school club that focuses on just 3 members:
- A serious boy who thinks a lot, and doesn't make a point of walking in groups unnecessarily
- A reserved/snarky/serious/introverted girl/who isn't honest with her feelings
- An energetic/kind/lively/outgoing girl/who is honest with her feelings
They spend much of the anime at the club fulfilling the requirements.
The protagonist doesn't have that much differential to draw attention in terms of appearance, but with his personality and actions he ends up conquering the two girls, they fall in love with him throughout the series and you'll have to watch to see which girl wins.
Both have a more serious vibe focused on
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Both center around students trying to find out who they are while dealing with a romantic love triangle. Yukino is very similar to Kazusa and Yui is very similar to Setsuna.
Both of them 2 girls and one guy, great romance, one tsunadere and one genki girl, only diff is the length and what is the anime adapting.
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Recommended by LacitoPapito