The phrase itself can be used as a noun, verb, or adjective, and defines something that is very obviously forcing an image onto its observer. This can be presented in a number of ways, including:
1) A person trying to convey an image that is unlike his or her actual self typically through large amounts of makeup
2) Something, such as a television show, attempting to mimic a more popular counterpart.
Amy is a Trying Too Hard; She's wearing a shirt meant for a 15-year old. It's too bad she's very obviously in her 40's.
Adam is Trying Too Hard to convince us that he's slept with Amy, the class whore.
Mission Hill is Trying Too Hard to be King of the Hill, as evidenced by its very title.
adj: Used by women
to describe men that behave appropriately and exhibit all of the qualities they desire. Purpose is to veto potential sex
candidates and prove that women can't accept positive attention. Undisputed proof that women don't know what they fucking want, but are pretty certain that they prefer being treated like shit.
Woman1: Reggie maintained a witty and intelligent conversation with me, took me out to a nice dinner, paid for everything, didn't try to get me drunk, and didn't take advantage of me when I passed out on his couch. I've been screening his phone calls all day because he was trying too hard.
Woman2: My boyfriend hits me during sex and not during sex.
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.