When Prince’s former protege,’ Denise “Vanity” Matthews, passed away in 2016, it shocked the R&B world to no end. Not many were more heartbroken than Vanity’s ex-boyfriend, Prince, though. Although their lives had gone two different paths in their latter years- Vanity became a evangelist preacher; and Prince continued his musical career- the connection they shared was deep. Little did most fans know, however, at the time of Vanity’s passing, Prince was also deeply heartbroken over the death of his very first high school love, who died just months before Vanity. It was the combination of those two heartaches, that some say led Prince into a deep state of sorrow and grief.

How Prince’s High School Girlfriend Died

Prince’s ex-girlfriend was Kim Upsher. The two former lovebirds attended high school together in Minneapolis, MN. She also had a small role in Purple Rain back in the day.

Although many fans knew how hard Prince had taken Vanity’s passing – he spoke publicly about it – according to Purple Rain actress, Jill Jones, his major heartbreak was due to Kim’s death. In a prior interview with Huffington Post, Jill (also an ex-girlfriend of Prince) revealed the facts about Prince’s largely unknown ex, Kim Upsher, and how he was affected by her passing:

Jill Jones on Kim Upsher- “She was the kindest, patient, and supportive person for him. Watching the changes that come into your life, I had a lot of empathy for her because she helped me navigate through all that bull—— at the beginning. She passed away before Denise so he had a double whammy. So I know everybody is like, ‘Oh, Denise’ but his girlfriend who has been with him, lived in the same house as him, grew up with him, that was his big crush from school…Kim was an unsung hero in my opinion. They stayed friends throughout. She knew his family, everything and it was sad. She passed away from a brain aneurysm and that sadden my heart.”

Fun Facts About Prince & His Ex, Kim Upsher

1. Kim Upsher had a cameo role in Purple Rain, as the waitress who Morris Day pretended to give a huge tip to, in efforts to impress Apollonia…

2. Friends say Kim Upsher was Prince’s first heartbreak:

Via Diffuser- Around the time of the album’s release, Right On! magazine (as quoted by PrinceSongs.org) asked the rising young sex symbol if he had a girlfriend. “I had one but she left me,” he revealed. “I wrote some songs about it on the album.” When the interviewer marveled at the number of women who would love to take her place, he explained a little more: “That’s why she left me.”

“I’m so alone / And brokenhearted / It ain’t like my life is ended / But more like it never started,” he laments on the silky smooth disco-era piano ballad. “I spend my nights just a-crying / And i spend my days just a-trying / To find that love to call my own.”

3. Kim and Prince attended Minneapolis Central High School together, which is also where they wrote, directed, and starred in a love story that mimicked their real life story.

4. Although Kim had broken up with Prince decades go, they remained friends throughout their lives.

Ms. Upsher passed away from a brain aneurysm on November 15, 2015. Exactly three months later, Vanity died from renal failure on February 15, 2016.

Sadly, the Purple One soon died just months after exes, Vanity and Kim Upsher. Some have alleged that although Prince died from an accidental overdose to prescription pain meds, he ultimately passed away from grief. May each of these kind souls continue to rest peacefully.