After trying and failing to meet her next match on Bravo’s Love Hotel, Ashley Darby’s love life is once again heating up—and her romantic interest is a familiar face: Josh Gudenburr. The two first met at a speed dating event on The Real Housewives of Potomac Season 9, Episode 10, and attended the White House Correspondents Dinner together in Season 10, Episode 2.
“Tonight, he’s going to be on my arm,” Ashley told her half-sister, Jessica in the Oct. 12 episode as she donned a ballgown. “Gonna be my arm candy.”
Ashley quickly caught viewers up on her ever-changing relationship status. “Josh and I had a pause,” she said. “I was very forthcoming with him that I needed to do Love Hotel, and he didn’t like that conversation.”
She also shared how they got back together, adding, “One day I got drunk and I hit him with a little [text] ‘Hey, Big Head…u up?’”
After producers showed Josh respond to her text with “lowkey, yes,” Ashley revealed, “We’ve been kinda kickin’ it since then.”
Details on Ashley Darby’s history with Josh Gudenburr
Ashley made it clear when she first met Josh exactly what she was looking for in a boyfriend.
“I’m really looking for somebody who has those qualities that could really be a life partner for me,” Ashley said in Season 9, Episode 10. “Someone who’s family oriented. Understands the idea of responsibility and commitment. Someone who’s very attractive. Well-endowed. And I’m honing in on those qualities now.”
As the two began dating during Season 9, Ashley admitted she was developing feelings for him. “Josh is a pretty great guy, and whenever we talk, it feels like everyone else in the room disappears,” she said at the time.
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Although the couple separated when Ashley checked into the Love Hotel, she dropped hints that they were still seeing each other when she appeared on the Jan. 12 episode of Watch What Happens Live with Andy Cohen and answered where she stood with Josh.
“We’re hanging out,” she told Andy. “He may have set me off this morning with a [big smile]. Yeah, he’s a good guy.”
She added of their relationship that they were “monogamous,” but didn’t have “labels at the moment.”
In the past, Ashley has showed reservations about Josh’s younger age, and those doubts still haven’t gone away the second time around.
“Josh is a really great guy. But I’ve never dated a guy younger than me,” she confessed in the Oct. 12 episode. “I think he needs a few more bumps and bruises, you know? A little more life.”
Still, Ashley pointed out there were many positives about Josh. “I do really enjoy his affection. He just wants to make me happy. However he can. And I really—I needed that,” she added.
Ashley Darby talks possibly having more kids while navigating dating
Although Ashley spent her time at the Love Hotel choosing between Wale and Ralph, she ultimately chose Ralph—and that relationship also faded with time. But, trying her hand at dating multiple men caused Ashley to realize more about herself and where she sees her life going. The mom of two also revealed if she’d want to have more children.
“I have to be realistic about everything involved,” Ashley told Wale in Season 1, Episode 3. “You want children. I’m not sure if I wanna have more children … And I am trying to be more selfish, you know what I mean? So, maybe it’s best just to let it breathe for a sec.”
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She also expressed she was unsure about having another child to The Daily Dish in December 2024.
“My answer changes every day,” Ashley at the time. “A lot of it changes when I date somebody.”
She added, “The ultimate answer is, ‘I don’t know.’ Part of the reason is that it’s so situational for me right now,” She also noted that she wants to find a partner who is a “good fit.”
As Ashley’s divorce from ex Michael Darby was finalized, find out more on why she declared “nobody is happy.”