Bryson Tiller's relationships have been both public and private, leading to speculation and intrigue among fans. One of the most notable relationships in Tiller's life was with his high school sweetheart, whom he dated for several years. Their relationship blossomed during his adolescent years, leading to an emotional connection that would later influence his music. However, like many young romances, it faced challenges that led to their eventual separation.
Another significant relationship was with Kendra Bailey, who was a prominent figure in Tiller's life for a substantial period. Their relationship was characterized by love, ups, and downs, and it was evident that Kendra inspired much of Tiller's music. Songs like "Exchange" and "Sorry Not Sorry" are believed to be reflections of their time together, showcasing the depth of his emotions and the struggles they faced as a couple.