Exes
When Did ‘The Challenge’ Exes Ashley K. & Dario Date & What Happened?

Ashley Kelsey and Dario Medrano are crushing it as rival partners on Season 5 of The Challenge: All Stars. The duo was partnered up due to their past relationship history — they were once a couple but have since broken up.
Since it’s been quite some time since these two have been in The Challenge universe, some fans may forget exactly how their love story began.
Kelsey and Medrano met on The Challenge: Invasion of the Champions, which filmed in 2016 and aired at the beginning of 2017. Despite being on different teams — she came in as a previous champion while he was a rookie — the two formed a connection and started dating after the show.
Things got really serious between the former couple. They were even living together at one point. However, they quietly broke up and had not spoken in years prior to filming the rivals All Stars season.
Although the exact date of their breakup is unclear, it seems that they split at some point in 2018. “I have not talked to the girl in six years,” Medrano said on The Challenge: All Stars premiere. The season was filmed in 2024.
This is the first time the two are publicly acknowledging their breakup, and Medrano is taking ownership for the romance ending. “I left her in the dust,” he admitted, with Kelsey adding, “I did not like this man when we broke up. I truly loved him.” Medrano also said he “was a dirtbag” and revealed that he still finds his ex “hot.”
Following the split, Kelsey moved on with Kerryon Johnson, a football player who’s 11 years her junior. They welcomed a daughter named Snoh Marie Johnson together in June 2021. However, by the fall of 2022, they had broken up and Kelsey began posting about her single status on TikTok.
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Of course, fans are now wondering if there’s a chance that Kelsey and Medrano are back together. “Y’all are gonna have to watch and see what unfolds this season,” she teased in a February Instagram Q&A. In response to a fan who pointed out that they “looked gooooooood together” on the show, Kelsey added, “We did.”
Before her relationship with Medrano, Kelsey dated her Real World: San Diego costar Zach Nichols. They met while filming the show in 2011. However, by the time they appeared on The Challenge: Battle of the Seasons in 2012, they had broken up.
Do you think Kelsey and Medrano are back together?! If not, do you think they should be? Let us know in the comments section below.
The Challenge: All Stars, Season 5, Wednesdays, 8/7c, MTV