When: 1989 – 1994

Before dating Kurt Cobain, Courtney Love had relations with Smashing Pumpkins member, Billy Corgan. By the early 1990s, however, Love and Corgan’s relationship had dissolved into a casual whenever-we-see-each-other arrangement. It was around that time when Love met Cobain. "The first time Kurt and I slept together was at a Days Inn in Chicago," she reminisced.

While her connection with Corgan had cooled down, things with Cobain were just heating up. The two got married in February 1992 and had their daughter Frances Bean later that year. Despite having a life most people could only dream of, Cobain famously battled inner demons that ultimately led to his April 1994 suicide. Following the Cobain tragedy, Corgan and Love were allegedly in cahoots during the Pumpkins’ Lollapalooza tour later that year.