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when in doubt, whip it out 

"It" is referring to showing your male genitalia to a certain lady (or guy if that's what your into).

This is the common reply you give to your friend when he continues to complain whether a certain girl is into him or not.

It's the ultimate test. If the girl doesn't take bait or if she's about to charge you for harassment, proceed to walk out the door and move on.
Pete: Hey Billy, Sara gave me a wink yesterday, but sometimes she doesn't seem interested in me.
Billy: Bro, when in doubt, whip it out!
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when in doubt, whip it out 

Common slang umong military enlisted to salute an approaching person in uniform when uncertain of their rank. Better to be safe than sorry. More common with the NAVY as Chief Petty Officers have gold anchors on their collars and are often mistaken for gold oak leafs (signifying a Lieutenant Commander or Major).
Bill- "Don't look now, but here comes an officer"
Larry-"No, it looks like a Chief Petty Officer from here"
Bill-"When in doubt, whip it out. Better to be on the safe side then to ignore him if he was an officer".
Larry-"You're right"

*Both saluting-"Good morning sir".

whip it in, whip it out and wipe it on the curtains

Yeah mate, when you see someone you like just go for it. Just Whip it in, whip it out and wipe it on the curtains.

When in doubt, whip it out 

Steve: my Penis is too warm

Emma: When in doubt, whip it out

National Whip It Out Day 

Dating back to the pre historic era national whip it out day is a day when men are permitted by the rules of nature to whip it out although men must control their most valuable cargo this holiday dose not apply to she-males or people who belive there is more than 2 genders and is also exclusive to men of all ages
Ricky: Hi Sally

Sally: Hey Ricky

Ricky: Happy National Whip It Out Day whips it out
Sally: OH wow look at the masterpiece happy National Whip It Out Day