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Air could work. Main character doesn't show much interest in anyone at first but gradually warms up to them. Drama is promised. Prepare your tissues!
Hmmm... AnoHana maybe? The group used to be really close at first but because of an accident and many other factors fell apart and most of them dislike each other now. Because of Menma all of them are gradually brought back together.
Another drama promise.
Great Teacher Onizuka has a whole set of complicated characters and some meet your requirement. Very strong series with unique characters, good development and bonding.
Nice comedy and some drama in between. Really worth a watch despite being old.
You could try Hakuouki Reimeiroku which is a prequel to Hakuouki series. Which ones you watch first does not matter in this series case but prequel fits better to what you want.
Main character hates samurais yet ends up under same roof as them.
If you want romance, then it will be Hakuouki Hekketsuroku.
In all honesty I would recommend to watch Reimeiroku first. If you like it then watch first season of Hakuoki and then sequel Hekketsuroku.
If you don't mind something darker then you can try Phantom: Requiem for the Phantom. Main heroine Ein is a professional assassin who doesn't care about anything but thanks to someone gradually learns to feel again.
Hope some of them will fit what you are looking for.
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