Trippie Redd, born Michael Lamar White IV, has captivated fans not only with his distinctive music but also with his often-publicized and sometimes turbulent romantic life. His relationships have frequently played out in the public eye, marked by passionate beginnings, dramatic splits, and occasional reconciliations, reflecting the intensity often found in his music.
His earliest public relationship was with fellow artist Aylek$ (also known as Angvish), which began around 2017. They reportedly met on Instagram, with Trippie Redd initiating contact. Their relationship was significant enough that Aylek$ released her debut single, "No Feels," in July 2018, which was widely understood to be about their breakup. Despite their split, their connection remained a topic of discussion, with Aylek$ recently asserting herself as Trippie Redd's "first love" amidst later relationship drama.
Following his relationship with Aylek$, Trippie Redd became involved with rapper Coi Leray in 2019. Their romance was brief but highly public and tumultuous, leading to a significant split that same year. Trippie Redd even released the song "Leray," which seemingly addressed their breakup, while Coi Leray also referenced him in her music.
After their initial separation, Trippie Redd entered a relationship with Skye Morales, which became public around 2021. Their relationship appeared more stable for a period, with Morales even featuring on some of his tracks, such as "Took My Breath Away." However, in August 2023, Trippie Redd publicly apologized to Morales on Instagram for cheating on her, stating, "She [may] not have had the best attitude with me, but she was the most loyal partner [I’ve] ever had and I lost her." This public admission marked the end of that chapter, with Morales reportedly not forgiving him.
In a surprising turn of events, Trippie Redd and Coi Leray rekindled their romance in August 2024. The reconciliation was confirmed when they announced on January 1, 2025, that they were expecting their first child together. Coi Leray shared joyful photos of them cradling her baby bump, with the caption, "I'm a rock star mommy we ready for 2025." This news suggested a new, more serious phase for the on-again, off-again couple.
However, the renewed relationship was quickly marred by public drama. In January 2025, shortly after announcing her pregnancy, Coi Leray posted a cryptic message on Instagram Stories, "THERE’S NOTHING WORSE THAN BEING CHEATED ON. I WOULD NOT WISH THIS PAIN UPON MY WORST ENEMY," hinting at infidelity. The timing strongly suggested Trippie Redd was the subject of her post.
Further fueling speculation and controversy, in April 2025, while Coi Leray was still pregnant with their child, Trippie Redd posted a mirror selfie on social media featuring an unidentified new girlfriend in his bedroom. This post ignited a social media firestorm, with fans and media outlets questioning the circumstances given Coi Leray's pregnancy.
Despite the public turmoil, Coi Leray gave birth to their daughter on June 16, 2025. While the romantic relationship between Trippie Redd and Coi Leray appears to have ended again amidst the cheating allegations and the emergence of a new partner, reports indicate they are committed to co-parenting their daughter. Trippie Redd's recent romantic history reflects a pattern of intense, public relationships, often accompanied by significant media attention and personal challenges.