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1.
Describes a situation where a heterosexual person can't truly determine the sexual orientation of a member of the same sex without engaging in an act that would question their own sexuality.

Also applies to any situation where a person who is, in fact, a heterosexual cannot proceed to do something that they want without strongly suggesting otherwise.
Ex. 1:
Guy 1: So what's the deal with Tom? Is he gay or what?

Guy 2: I don't know...Its hard to tell.

Guy 1: I guess one of us could go over there and try to make-out with him, but its a catch 69.

Ex. 2:
Guy 1: Hey, straight guys can wear skinny jeans, right?

Guy 2: Well sure straight guys can wear skinny jeans...its just that those guys tend to engage in sex with other men...
by tonyDaDickDealer June 16, 2009
 
2.
1) Derived from the term "Catch 22," a Catch 69 is when two people engaging in the 69 position (that is, when both have their mouth on the other's genitals) are linked together by a lip or tongue piercing and a genital piercing.

2) This has also been used to reference an eyebrow ring getting caught in pubic hair.

3) Pubic hair caught in one's teeth after engaging in a 69.
1) "Excuse me doctor, but we appear to have another Catch 69 in the waiting room. She's been on her knees for an hour and I like to think people aren't that determined."

2) "Sorry sir, but I can't hire you on account of your eyebrow ring."
"You said piercings were fine!"
"Not when they have public hair in them."

3) "You have something in your teeth."
"Is it salad?"
"Only the thoroughly tossed variety."
by hermia.tamerlane April 13, 2010
 
3.
win win situation
my friend gets to choose between ten thousand dollars in cash or a new bmw, he is in a catch 69. either way its a win win situation.
by xxxsketchxxx March 25, 2011