From on-again, off-again relationships to whirlwind engagements, Pete Davidson has had a rocky dating history. Following a brief engagement to Ariana Grande in 2018, Davidson didn’t turn his back on romance with fellow A-Listers. Davidson began romancing actress Margaret Qualley several months later until October 2019 before he rebounded with the likes of Kaia Gerber and Phoebe Dynevor. Nearly three years later, Davidson met Kim Kardashian in Oc…