:max_bytes(150000):strip_icc():focal(979x358:981x360)/kristin-cavallari-35a1d4e1a65c40b1bdf9967b4065ea10.jpg)
Dye’s romantic history highlights a recurring crossover between the comedy circuit and television personalities. Below is a structured breakdown of the defining chapters in his dating life, centered on the high-profile Cavallari era and its eventual disintegration.
| Timeframe | Partner / Subject | Key Developments & Milestones |
|---|---|---|
| 2018, 2019 | Becky Lynch | Dye dated the WWE superstar quietly before Lynch began dating her future husband, wrestler Seth Rollins. |
| Oct 2020 | Kristin Cavallari | First spotted kissing in Chicago shortly after Cavallari announced her divorce from Jay Cutler. |
| Dec 2020 | Kristin Cavallari | The couple traveled to Cabo San Lucas, Mexico, openly displaying affection at their beachfront resort. |
| Mar, Apr 2021 | Kristin Cavallari | The romance fizzled out due to long distance, single parenthood priorities, and differing lifestyles. |
| Dec 2023 | Public Conflict | Cavallari discussed Dye’s Burbank DUI on her podcast; Dye blasted her on a separate show, shouting "F, k her." |
| 2024, 2026 | Independent Paths | Dye leaned into touring comedy dates and political controversy; Cavallari dated model Mark Estes. |
