Dunno if you've seen the anime Toradora! But I'm looking for something similar but as a drama. Basically the two leads help each other win the hearts of their respective crushes, but in the end they fall in love with each other instead.
I didn't watch it for a while but I think Witch Yoo Hee fits your description quite well.
You might like 'Date'  http://mydramalist.com/12468-date-koi-to-wa-donna-mono-kashira
I haven't seen Toradora, but how you're describing it sounds similar to Birth Of a Beauty 
Hi, I think two dramas have half of what you want:
Personal Taste and Oh my venus: in both dramas the male lead helps the female lead to regain their charm and her ex-boyfriend, but in the process they fall in love.