Im a guy and i like these type of drama too, infact i like these more than the typical action dramas. It Sounds like youre looking for a drama with average guy scoring big with a rich girl ;)
Innocent man (guy lives in a poor neighborhood. Gets with a rich girl) moon chae won and park si yeon are most good looking actresss in my opinion
That fool (commoner gets with a famous actress)
This one isnt korean, its japanese but you might want to consider
densha otoko (geeky figurine collector gets with a rich girl)