Once upon a time, Orange Is the New Black star Jackie Cruz was pretty close with Kourtney Kardashian. O.G. Keeping Up With the Kardashians fans will remember the time the oldest sister sparked a little fling while filming Kourtney & Khloe Take Miami in 2009 and was captured exchanging a kiss with a brunette beauty. While we didn’t know it at the time, Kourt’s very friendly gal pal, was in fact, the actress and songstress. Although we once knew Jackie as the girl that Kourtney met in art class, and later Kourt’s hot tub lover (who Scott Disick flashed), fans are dying to know more about their relationship now that Jackie has public recognition.