I'm a 25 year old currently working on a fairly prestigeous degree (already have my undergrade), so I don't really "self insert" and to be honest I don't think I ever did in the first place.
However, I do remember what it's like not being the cool guy and feel a certain kinship with younger guys in that position.
That said, I'm kind of picky about who I like. Renji from EF: A Tale of Memories (not a harem show, but targetted to a similar audience) is my personal favourite example of the - his whole shy bookworm shota thing is really endearing. My support is not only demanded but given freely!
Shingo from Mashiro-Iro symphony is another favourite - I liked his diplomatic ideals, which I connected to in the way I can't really connect with extremely masculine protagonists despite considering some of them a riot to watch.
In contrast... well, Sumeragi mentions Amagami. Junichi definitely was not a favourite, as much as the show did a decent job detailing how he won over the girls he still came across to me as far, far from the best there is among quiet, seldom noticed guys. Plus, I found him too moppy.
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Signature courtesy of Ganbaru.
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