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a horrible pixelated shot of an underdeveloped highschool freshman in their underwear trying their best to make a seductive face 

The default picture used by over 84% of users of the popular networking site myspace (See definition #4).
-Man, she looks fine!
-Can't you tell? That's a horrible pixelated shot of an underdeveloped highschool freshman in their underwear trying their best to make a seductive face, dude.

Trying to hold this wood 

A pickup line used on girls in Marbella that has a 100% success rate.
"Alright girl, where you from? I have an apartment 5 minutes away. You trying to hold this wood?"

monkey trying to fuck a football 

monkey trying to fuck a football attempting to perform a difficult or almost impossible task
a lineman was attempting to change a street light bulb it was like watching a monkey trying to fuck a football

trying too hard 

This occurs when someone attempts to prove how they possess a perceived desirable quality by over-exerting themselves which results in the quality appearing unnatural and contrived. Generally, the response to this action is negative and has the opposite effect.
Guy 1 - John thinks he is so tough because he grunts when he lifts weights.
Guy 2 - Ya, his Napoleon Complex is showing, he is totally trying too hard.

Girl 1 - Andrea is trying too hard. She thinks she is so hot when she pops her cleavage and shows her ass.
Girl 2 - Whatever, that skank doesn't realize we can see her cottage cheese thighs in that mini-skirt.
trying too hard by ncojay September 17, 2013

or die trying 

1. No matter what dangers or difficulties are involved.

2. To the greatest degree or extent; completely or entirely.

SYNONYMS: at all costs; at any cost; to the fullest; whatever it takes
Get rich or die trying.
-50 Cent

We’ve been trying to reach you about your car’s extended warranty 

A scam call about something that should have been sent in the mail
"We’ve been trying to reach you about your car’s extended warranty"
" i dont have a car , im 10 years old"