look up any word, like sweetest day:
 
1.
The development of misunderstanding the Free Rider problem.
Somebody mistook Free Rider as Day Rider, which in turn somebody else mistook Day Rider to Gay Rider.

See information failure
by Strawberry Clock Version 2 March 19, 2004
 
2.
A phrase used to describe something as being bad or having gone wrong.

The word "Gay" meaning the negative connotation of Homosexual and "Rider" is used as a nonsensical verb.
Example

Person 1: was about to get this hot bitches number and then she told me she had a boyfriend.

Person 2: Thats Gay Rider!

Example

Person 1: Yo we dont have tickets for the playoff game.

Person 2: Why not?

Person 1: Todd stiffed us and took someone else.

Person 2: Awww c'mon thats Gay Rider.
by K Ding May 07, 2006