‘Still Waiting’ Finds Prince Nursing His First Broken Heart: 365 Prince Songs in a Year

To celebrate the incredibly prolific, influential and diverse body of work left behind by Prince, we will be exploring a different song of his each day for an entire year with the series 365 Prince Songs in a Year.

Sometime before the recording of his self-titled 1979 sophomore album, it seems Prince got his heart broken for the first time. Naturally, he channeled that pain into songs such as the record's third single, the achingly sweet "Still Waiting."

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."

Testimony from various friends identifies the young woman in question as Prince's high school girlfriend, who inspired his student film project. "He had a crush on a girl named Kim Upsher," his classmate and friend Robert Plant (not that one) explained to the Star Tribune. "So the movie was about him trying to get the girl. Paul Mitchell played the team quarterback - which he was - and every time Prince was with the cheerleader, Paul would come by and push him out of the way and walk away with the girl."

Determined to vanquish his foe, the film shows the future Purple Rain star reading up on Kung Fu in the school library. For the big finale, "Prince pulls this kung fu move and walks away with the girl." Sure enough, Prince also won Upsher's real-life affections. Future Revolution bassist Brown Mark shared a funny story about the couple from 1976, when he was an aspiring musician working as a cook at the same restaurant where Upsher was a waitress.

"This little guy with the big Afro walked in, I was sure it was him — I was freaking out. So Kim comes running into the kitchen and says, ‘I need you to cook the best doggone pancakes you ever made!’ And I was like, ‘Is it for Prince?!’ Let me tell you, I cooked some absolutely delicious pancakes for that man."

While still dating Prince, Upsher later shared an apartment with another future member of the Revolution, Lisa Coleman, and in the summer of 1978 helped Prince decorate his first house so it looked "like a home" instead of a nearly empty space over a basement full of recording equipment.

At some point in the next year, the relationship reportedly ended. But even after Prince and Upsher split they remained friends. You may remember her cameo as the waitress Morris Day rather transparently pretends to give a generous tip to in Purple Rain.

Upsher died of a brain aneurysm in 2015. It has been suggested that Prince paid for her funeral. "They stayed friends throughout.. she was the kindest, [most] patient, and supportive person for him," former Prince collaborator (and romantic partner) Jill Jones told the Huffington Post. "[She] 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."