It's like a parody on the romcom manga. I just hope it won't end up like "Why Can't Seiya Todoin, 16-Year-Old, Get a Girlfriend?" where along the way the humor turned into torture.
P.S. He's basically trying to become a dominant "shoujo" protagonist(rich, cool and attractive) while the other guy is an epitome of shounen protagonist (clumsy, average in everything and one way or another related to the heroine).