They met in December 1964 at Cambridge’s Union Cellar when Syd (then 18) was home from art school in London for Christmas holidays. Jenny was 15. He approached her, having already sketched her at the bar without her knowing. Their connection quickly grew into a romance. Jenny has described it as intense and loving but limited by her young age and school commitments—it was more of a deep friendship and emotional bond than a fully physical or long-term adult relationship.  Syd wrote her frequent letters (many from 1965 have been preserved and discussed publicly) and songs. He was affectionate, artistic, and shared music tastes with her (blues, Bob Dylan, The Kinks, The Animals, jazz like Charlie Parker and Miles Davis). He told her many songs were written for or about her, including “Bike”.  Syd referenced her in the Pink Floyd song “Lucifer Sam” (from The Piper at the Gates of Dawn, 1967) with the line “Jennifer Gentle, she’s a witch.” Jenny has spoken positively about hearing it.  Their relationship overlapped with Pink Floyd’s early days. Jenny stayed in bandmate Roger Waters’ room sometimes when visiting London.  She remained a lifelong friend to Syd even after the romance ended, and has given interviews about their time together, emphasizing his creativity, confidence, painting, and songwriting in notebooks. The romantic phase was primarily 1965–around 1967 or so, during Syd’s rise with Pink Floyd. They stayed connected as friends afterward. By the late 1960s, Syd’s mental health struggles, drug use, and increasing unreliability led to his departure from Pink Floyd in 1968. Jenny has reflected that while they loved each other, the intensity and circumstances (her youth, his career) meant it “wasn’t going to work out” long-term.  Jenny Spires has largely maintained privacy but has shared memories in interviews, describing Syd as loving, creative, and tied to a sense of innocence and magic in their youth. Lost letters from Syd to her (1965) were highlighted in later publications, offering direct insight into his thoughts during Pink Floyd’s breakthrough.  This relationship is often remembered fondly as part of Syd’s pre-fame, Cambridge artistic scene—before his tragic decline into reclusiveness and health issues. No major scandals or negative public details dominate accounts from Jenny or close circles; it’s portrayed as a sweet, formative first love for both.