Something ilke Itazura Na Kiss but in reverse...

[stormchasar]

So eburinyan, the weeaboo world is flooded with anime and manga about people who have a crush on someone smarter, better looking, and more popular than themselves that they eventually land. What I'm looking for is the opposite. Someone with a crush on a kouhai or a stupid person or whatever. Does such a thing exist?

[DeX-kun]

Originally Posted by stormchasar

So eburinyan, the weeaboo world is flooded with anime and manga about people who have a crush on someone smarter, better looking, and more popular than themselves that they eventually land. What I'm looking for is the opposite. Someone with a crush on a kouhai or a stupid person or whatever. Does such a thing exist?

Although it's not necessarily the opposite in the sense that the person has a crush on someone stupid or even a kouhai (considering the 2 people are in the same grade,) but Kare Kano might be something you're interested in since it's the smart handsome guy that is in love with a seemingly perfect cute girl (I say seemingly because the way she acts around her classmates is completely the opposite of who she is in reality.)

She's not exactly naturally intelligent but rather she studies very hard to maintain high grades, even so it's a very good series although the ending was never really completed but it's still a good watch (or even better, read the manga which actually ends the plot.)

The full Japanese title is "Kareshi Kanojo no Jijou" or "His and Her Circumstances" in English.

[MikaMiaka]

One thing that pops to mind is La Corda, where basically all the uber-talented guys are into the heroine, but she severely lacks any natural talent. I liked it a lot, it was a lot of fun to watch. If you liked Kiss then I think you would enjoy LC if you have not already seen it.

And in Good Witch of the West , the heroine likes the nerd, though this is NOT a romance title, it's fantasy and adventure -- but again, if you liked Kiss, you might like GWOTW .

Edit:

And if you're not opposed to BL, there's a lot of BL titles where the dominant, perfect and rich dude also chases after the clueless, simple minded but pure hearted prey (e.g. Junju Romantica)

[oompa loompa]

Originally Posted by stormchasar

So eburinyan, the weeaboo world is flooded with anime and manga about people who have a crush on someone smarter, better looking, and more popular than themselves that they eventually land. What I'm looking for is the opposite. Someone with a crush on a kouhai or a stupid person or whatever. Does such a thing exist?

school rumble is probably the closest that I can think of - but thats pretty much what a lot of the story is about - characters loving other 'stupid' characters. it was one of my favorite shows, and was the first show that got me into anything apart from shounen.. however.. watch at your own risk ->

Spoiler for spoiler:

I dont want to put you off.. but it has one of the worst endings ever. infact, its more incomplete than an actual end.

[Rab]

Special A I think fits the bill here.

http://en.wikipedia.org/wiki/Special_A

[Tiran86]

Special A sorta fits, he's definitely better at everything, but she's not exactly a loser. She's still second place in pretty much everything.

[Saleh]

Most harem may meet your criteria (eg. Saiunkoku Monogatari, Fushigi Yuugi, Cresendo...).

Spoiler for Skip Beat (Manga):

In skip beat Tsuruga Ren(Kyouko' Sempai) and Shoutaro have a crush on Kyoko

[cerrian]

Believe it or not, Haruhi is definitely like that, but then again so is Clannad. Although in the case of Haruhi, she's more of an outcast than a loser but definitly somebody everyone else avoids. In between the two would be I'd put Touka Gettan because Momoka is a bit random like Haruhi but has a moe side of her like most of Clannad's cast.