A Look At Landman Star Michelle Randolph's Real-Life Dating History

Michelle Randolph, who plays Ainsley Norris on the mega hit "Landman," has explored a couple of different onscreen relationships since joining the cast. She's also found time to explore finding love in real life, even though she has a thriving acting career. However, we definitely think her personal romances have been considerably less eventful than Ainsley's romantic arc over the years. In fact, the actor seems to fully devote herself to her relationships. As of write time, that appears to be with actor Glen Powell.

According to People, the photogenic pair first incited romance buzz after a sleuthing fan recorded them getting quite chummy at a dance hall in Texas in November 2025. Powell's mother was also in attendance, which suggests that their relationship was actually heading somewhere. "He danced with both his mom and Michelle, and the two already seem to be two-stepping experts," a source told the outlet. That said, neither party confirmed a romance at the time. Then, March 2026 saw the actors holding hands in public, while June had them sending the biggest hint thus far that they're dating: They were photographed kissing in New York City.

However, Randolph doesn't appear too eager to open their romance completely up to the public. "I think, for peace of mind, those are really important for me to keep separate," she told InStyle about her love life in January 2026. "How people perceive you publicly is not who you are." Of course, this isn't Randolph's first rodeo with a fellow star.

Years before Michelle Randolph started dating Glen Powell, she was romancing another famous actor: Gregg Sulkin. Although it's unclear when their courtship actually started, their public relationship seemingly kicked off around October 2018, when Sulkin gushed about Randolph in a since-deleted Instagram snap. "Thank you for coming into my life & making it better. I love you," he wrote (via Us Weekly). And while the next few years would produce considerably fewer public declarations, it's been speculated that their relationship lasted into 2023. To this day, however, neither has addressed their relationship or split in a public forum. Interestingly, it doesn't appear as if the gossip blogs have the tea either, so it's likely that, as TMZ previously noted, they remained friends after the breakup.

Like Randolph, Sulkin has also set his sights on new love. According to TMZ, he struck up a romance with British model Freya Tidy near the end of 2024. From the sound of things, their relationship was the real deal, as Tidy had already packed up her life back home to bask in the California sunshine with her new beau. With that said, the outlet also noted that neither star had formally confirmed their relationship either. 

Regardless, Just Jared published a photo of them hiking and engaging in light PDA in July 2025. Additionally, they've both appeared in several of each other's photos on Instagram. As of write time, their latest lovey snap was uploaded to Sulkin's page in June 2026.