Are there any shows where the main guy is weird and/or nerdy plus not rich? Doesn't have to be outright poor, but nowhere near as rich as the second guy. They both are in love with the main girl who is pretty. She likes the second guy, but then falls for the main guy in the end.

In Time with You

Dream High

Corner in Love ( Taiwanese drama, it's perfectly match what you re looking for)

That fool ( I dropped it at ep.4 but IMO the story will match )

Big Man ( really nice story )

protect the boss but he's also rich 

Maybe you should try just between lovers. The second male lead is a successful engineer and themale lead is poor but he is not a nerd or a weirdo. 

I know these aren't 100% what you're looking for but you might enjoy these three as well :)

https://mydramalist.com/185-celeb-to-binbo-taro - He is a poor widow father of three and she is a daughter of the hotel chain mogul.

https://mydramalist.com/269-densha-otoko - He is just an otaku who is also veeery introverted and shy while she is your regular office worker but still has money to buy products from Hermes.

https://mydramalist.com/12380-ho-goos-love - He is somewhat nerd and weird while she is one of the members of the school's swimming team and also (if I remember right) is one of the school beauties. Then these two meets later on and anyways this is so good !