Mario knows how to get ALL the ladies. Not romantically, of course, but he knows how to get them because they're usually trapped in a dungeon and he's the only one bothering to save them. I mean, there's a reason he's like 45 years old and still living with his brother and his "girlfriend" basically never spends any time with him.
So, yeah, Mario? Middle-aged, embarrassing outfit, generally pathetic, obsesses over a girl who doesn't like him that much...he would totally be a creepy pick-up artist.