This mutual interest has been in the works for while. Back in 2018, the Pretty Little Liars actress went on People TV and talked about how much she was looking forward to seeing Underwood as the Bachelor that year. "I'm super excited that Colton's the Bachelor," she said. "He's wholesome. He's a good guy it seems like. He's really beautiful to watch." They also have mutual friends, according to TMZ. The outlet also reported that Hale slipped into Underwood's DMs shortly after his breakup with Randolph, and the two "have gone on a few of these 'casual hike dates' over the last few weeks."
But like most Bachelors, drama always manages to continue to follow him around. Right now, it's with his ex, who called him out last week for "monetizing their breakup" by including a chapter about their relationship and breakup in his upcoming memoir, The First Time: Finding Myself and Looking for Love. While the two had what seemed like a relatively amicable split in May, Underwood publicly criticized Randolph and, according to the grad student, painted her in an unfavorable light, when she talked about her relationship with Underwood on The Bachelor's "Greatest Seasons Ever" special. She maintains that she intentionally kept things vague, and that Underwood has a "double standard."
"On Monday evening, you informed me you intend to monetize our breakup by writing a new chapter to discuss your experience with COVID (where you stayed in my family's house during your recovery) & about our breakup," Randolph wrote on her Instagram story. "You have also refused to give me any sort of approval on the chapter you will be writing, which will heavily feature me... This seems a bit unfair to me."
Nevertheless, the messy baggage that seems to come with the Bachelor territory seems to have not kept Underwood from his ongoing quest to find the one, so we expect to see many more "casual hike dates" from him in the near future (hopefully with a mask, next time?).