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Trainwreck 

Someone who has very little idea of what they are doing with their life and is most likely set up for failure.
That girl has serious jealousy problems. Her family life isn't good either. Lets not talk about her grades… If she doesn't do anything about it, she'll be a trainwreck.
Trainwreck by stejedasa July 4, 2015

Trainwreck 

When a mishap or coordination issue occurs in sex causing the penis to bend.
My boyfriend got a trainwreck last night. He was plowing my ass so hard he didn't notice when his dick slipped out and stabbed my taint.
Trainwreck by Mouthy Broadcast September 14, 2016

Trainwreckstv 

squadW or something idk i dont watch twitch
squadW
what?
like, ape gang?
Jesse what are you talking about.
Trainwreckstv, bro.
shut up.

trainwreck 

Sex between 3 men and a woman in which one man inserts his penis in her vagina, a different man enters her anus, and the third member receives a blowjob from her at the same time.
Your mom got trainwrecked last night when those 3 guys from bingo night all had sex with her at the same time.

or

What happened to "secret" when Phyllis and May piled on him!
trainwreck by sunshine September 19, 2004

trainwreck 

Britney Spears in general, highlighting many Britney incidents such as her comeback on MTV's recent Video Music Awards, fumbling her baby, showing her cooter and shaving her head, just to name a few.
The 2007 VMAs were home to the biggest trainwreck comeback of the year.
trainwreck by Ashl and Krissy September 25, 2007

trainwreck 

Very potent marijuana that will get you very high and fucked up. It is called trainwreck because you are so messed up. Although real trainwreck is natural fake trainwreck is normally laced with other drugs.
One hit of this trainwreck will fuck you up.
trainwreck by lajoiester October 27, 2005