Ariel Pink - Put Your Number In My Phone. Eclectic as ever. If anyone figures out what's going on in the video, I'd like to know.

I thought it was pretty straightforward? The protagonist/singer has some sort of crippling medical condition, and is lonely and seeking female companionship (disabled men need love too; see also Neutral Milk Hotel's “Two-Headed Boy, Pt. 2”). So he's boned up on PUA, and he's hired a young guy to assist him, appropriately peacocked up with the hair and hat and lipstick etc, and they've gone to the mall to hunt for phone numbers (one of the key steps). He fails dismally, as one would predict. This is a mix of sad/pitiable and optimistic: it may seem hopeless, and he has indeed failed, but there is always tomorrow, and if they make enough approaches, who knows? Maybe one day they'll succeed.

(I realize that watching it, you might think the scenario is that it's a young PUA forced to drag along his crippled older brother, completely ruining his chances, but this does not fit the tone or lyrics too well, and if you watch carefully, there seems to be hints that the wheelchair man is in charge; consider the phone tapping at 2:10 - it's not the young guy's phone which is the subject of the title, but the wheelchair guy's phone.)