Win Some, Lose Some

Album: Dark Sky Paradise (2015)

Songfacts®:

  • This ballad finds Sean dealing with some of his personal problems as he talks about how his life has changed since he has became famous. He discusses on the first verse how his relationships with friends have been affected by the long hours he puts in resulting in him having little time to return to the hood. The next verse finds Sean noting how he thought his ex Naya Rivera was going to be the one, but eventually realized there was just too much drama in their relationship.
  • Sean said during a listening session that titles like "Paradise" "and this one depict what he called the "high points and low points" of chasing a dream.
  • Jhene Aiko joins Sean on the hook. The Los Angeles songstress previously collaborated with the rapper on his Hall of Fame track, "Beware."

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