I might hit the club, find a chick that's tailor
Made for me,
1) It’s an analogy for saying he is going to find a chick that is made for him just like suits are tailored to fit you perfectly.
2) Remember that last line about Oscars?
He’ll HIT the club, referring to retired boxer, Oscar de la Hoya.
Finding a girl that’s TAILOR-MADE for him refers to Oscar de la Renta, a Dominican-American Fashion designer.
3) This is a golf play on words. Taylor Made is a brand of golf club. So Em’s gonna hit the club (go to the nightclub) or (hit the golf club) and find a chick that’s tailor made (made to fit just him) or (is the Taylor Made brand).
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