The Tumultuous Love Life Of Trippie Redd: A Complete Timeline Of Girlfriends And The Coi Leray Baby Drama (Updated December 2025)

The romantic life of rapper Trippie Redd, born Michael Lamar White IV, has been as vibrant and chaotic as his music career, constantly making headlines and fueling social media speculation. As of December 2025, the 'Love Scars' artist is navigating the fallout from one of his most public and dramatic relationships yet, which included a shocking pregnancy announcement and a very swift breakup.

The past year has been a rollercoaster for the 'A Love Letter to You' star, culminating in a highly-publicized rekindling of his romance with a fellow rapper, followed by a dramatic split. This deep dive into his dating history uncovers the full timeline, the major figures in his life, and the current status of his love life following a turbulent 2024 and 2025.

Trippie Redd Biography and Complete Dating History Timeline

Michael Lamar White IV, known professionally as Trippie Redd, has cultivated a distinct persona in the hip-hop scene, characterized by his unique blend of emo rap and trap. His personal life, particularly his dating history, has often been intertwined with his musical output, with many of his tracks referencing past loves and heartbreaks.

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• Full Name: Michael Lamar White IV
• Stage Name: Trippie Redd
• Born: June 18, 1999
• Birthplace: Canton, Ohio, U.S.
• Age (as of December 2025): 26
• Occupation: Rapper, Singer, Songwriter
• Genres: Emo Rap, Trap, Soundcloud Rap, R&B
• Breakthrough Albums: Life's a Trip (2018), A Love Letter to You 4 (2019), Pegasus (2020)
• Current Relationship Status (as of December 2025): Unconfirmed/Single (Following a very recent split)

Key Figures in Trippie Redd's Relationship Timeline

Trippie Redd's love life has been public since his early career, featuring several high-profile relationships that have influenced his music and public image. The most notable relationships are:

• Aylek$ (Angie Diaz): (2017–2018) – One of his earliest and most turbulent public relationships. Aylek$, a model and aspiring rapper, was frequently featured on his social media and is often cited as the subject of his early heartbreak tracks. They had an on-again, off-again dynamic, and there was speculation about a reunion even in 2025.
• Emani 22: (2017–2018) – A brief but documented relationship during a busy period of his career.
• Mulan Vuitton: (2017–2018) – Another short-lived relationship that occurred during his rise to fame.
• Bhad Bhabie (Danielle Bregoli): (Mentioned in history) – Though never a confirmed long-term relationship, she has been linked to him in his early career.
• Coi Leray: (2019; Rekindled 2024–2025) – A fellow rapper whose relationship with Trippie Redd has been one of his most scrutinized. They first dated in 2019, but their rekindled romance in 2024 led to the biggest news of 2025.
• Skye Morales: (2021–2023) – A model and social media personality with whom Trippie Redd had a significant, long-term relationship that lasted for about two years before their eventual split in 2023.

The Coi Leray Chapter: Pregnancy, Cheating Allegations, and 2025 Fallout

The relationship between Trippie Redd and Coi Leray dominated headlines from late 2024 into early 2025, providing the most dramatic update to his dating history in years. Their on-again, off-again dynamic was fully "on" when they rekindled their romance in August 2024.

A Shocking New Year’s Day Announcement

The biggest news came on New Year’s Day 2025, when Coi Leray publicly announced that she was pregnant and expecting a baby with Trippie Redd. The news of their impending parenthood, which they publicly embraced, was met with a massive reaction from fans and the hip-hop community, confirming their status as one of the industry's most high-profile couples. They were reportedly ready for their new chapter together.

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The Swift Collapse of the Rekindled Romance

Despite the joyous announcement, the relationship quickly unraveled. Reports indicate that the happiness surrounding the pregnancy only lasted approximately three weeks before the couple split, leading to a massive social media fallout.

The breakup was reportedly fueled by cheating allegations. Coi Leray later publicly expressed regret for making claims that Trippie Redd had been unfaithful, suggesting the drama was intense and highly regrettable. The public nature of the split, especially with a baby on the way, made it a central topic of discussion throughout the first half of 2025.

Who is Trippie Redd Dating Now? The December 2025 Status

Following the dramatic end of his relationship with Coi Leray, Trippie Redd's current dating status has been a source of constant speculation. As of December 2025, his love life appears to be in flux, with rumors of a new interest and a possible return to an old flame.

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The Mystery Woman and New Girlfriend Rumors

In the months following the Coi Leray breakup, Trippie Redd caused a stir by posting photos of a "mystery woman" on his Instagram with no context, leading to immediate speculation that he had moved on. This was further fueled by reports that he had "debuted his new girlfriend" while Coi Leray was in the late stages of her pregnancy. The identity of this new partner remains largely unconfirmed, suggesting a desire for more privacy after his last highly public relationship.

Speculation of an Aylek$ Reunion

Adding another layer of complexity to his dating timeline, social media detectives and news outlets began speculating about a potential reunion with his ex-girlfriend, Aylek$. The two were reportedly seen together in New York City, which immediately sparked rumors among fans who remember their tumultuous history. While a full romantic reconciliation has not been confirmed, the sighting indicates that Aylek$ remains an entity in his life, years after their initial split.

Given the highly-publicized drama and the rapid introduction of new potential partners, it is safe to say that Trippie Redd is not in a stable, long-term relationship as the year 2025 comes to a close. His focus appears to be on navigating his personal life while continuing to work on new music, including a joint album with Machine Gun Kelly (MGK). The arrival of his first child with Coi Leray will undoubtedly mark the next major chapter in his personal life, regardless of his romantic entanglements.