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The Gatsby Effect 

When the subject becomes wrapped up in feelings that are dictated by the need for an unobtainable dream. The person can seem incredible irrational and borderline obsessive. The subject may or may not be aware of dream being unattainable. If they are aware, a dilemma most often will occur in regards to pursuing the goal or dropping it. While one answer seems correct to outside people, they will seem equally as hard to the subject.
'Why doesn't Fred just stop talking to Sally. He has to know nothing is there for him. He is simply wasting his time trying hook up with her again. Ok, maybe they had something 7 years ago but come on he just needs to move on'

'He is a classic example of The Gatsby Effect.'

Great Gatsby 

The act of Eiffel Towering a girl while cheering a Nattie or Keystone Light. Patented in THE Ohio State University by the bros of 1830. Also some book
Shaf: Did you see that asian chick?
Matt: We'll Great Gatsby that this weekend
Vince: THERE IT IS!!!
Great Gatsby by 1830 Bros January 24, 2011

The Great Gatsby 

To attempt to cum into a girl's mouth, but miss. Named after the novel, "The Great Gatsby".
Person 1: Julian tried to cum into this chick's mouth, but his cum didn't shoot far enough and completely missed the target.

Person 2: That sucks! Julian pulled "The Great Gatsby".
The Great Gatsby by Average Angel September 16, 2011

Sending Gatsby back home

A euphemism for sexual intercourse, presumably derived from the fact that Gatsby lived in a place called "West Egg." The resulting euphemism implies that the sex is intended to result in pregnancy.
Matt- "Dude, when I go abroad next year I'm gonna be 'sending Gatsby back home' all night, every night!"
Dave- "Matt, the last thing we need is a whole shit ton of pregnant furries."

The Great Gatsby 

‎"Daisy tumbled short of his dreams, not through her own fault, but because of the colossal vitality of his illusion...no amount of fire or freshness can challenge what a man will store up in his ghostly heart." F. Scott Fitzgerald
The expectations of his relationship with Daisy did not meet with reality in F. Scott Fitsgerald's "The Great Gatsby."

Pull a Gatsby 

To throw a party only to mope about and not engage or interact with the guests. The intent of such an action is usually to set an unknowing trap for a long lost love.
Jeff decided to pull a Gatsby after Carol broke up with him. Poor bastard was trying to win her back with his Wii and awesome vinyl collection.