Hate it when that happens 

Yeah, hate it when that happens. Don't you???!!!1

<two people talking about something (possibly computer related)>
Me: "Yeah, hate it when that happens!"
Them: "Just piss off, you dribbling spastic!"

Hate it when that happens by Josherick #3 January 29, 2005

I hate it when that happens 

A phrase often used to sound empathetic when in most cases the scenario being discussed is too unique for the other person to have possibly gone through the same situation.

Person #1: Dude you won't believe this, but I saw Jeremy on my flight! I have never seen someone I know at the airport let alone on my plane!
Person #2 Yah, I hate it when that happens.
Person #1: What?!

I hate it when that happens by The Empress of the Universe June 16, 2011

I hate it when that happens 

The act of getting your pubes stuck under your helm.

Jamie has a short penis and long pubes and thus had a case of 'I hate it when that happens'.

I hate it when that happens by Matt G June 7, 2004