RHOBH’s Diana Jenkins And Asher Monroe’s Relationship Timeline

A second chance at romance! Real Housewives of Beverly Hills star Diana Jenkins’ marriage to Roger Jenkins may not have worked out — but she found love again with fiancé Asher Monroe.

Diana and Roger met in 1999 and were married for 10 years before calling it quits for good. The former couple  — who share son Innis, born in 2000, and daughter Eneya, born in 2002 — remained on amicable terms despite their split, calling it the “happiest divorce ever.”

“Will she take half my money? Of course,” the banker told the Daily Mail at the time. “Without her, I would not have anything like the success I’ve had. I love Diana and have such admiration for her as a mother, businesswoman and someone who was brilliant as a wife. We have moved on and are supremely happy with the arrangements we have in our lives. Diana will always be a very happy part of my life.”

Diana met Monroe while attending a Victoria’s Secret fashion show in 2010. While the Bosnia native initially wasn’t looking for anything serious, the twosome grew closer and even cofounded independent record label D Empire Entertainment in 2012.

In 2021, the “Here With You” musician opened up about the ways in which the reality star has helped him in his career.

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“[Diana] has stood by my side through thick and thin,” he gushed to Pop Hearts TV at the time. “Without her, I would not be the man I am today. I have always looked up to her in the way she runs her life. Being a role model, war survivor, philanthropist, mother, entrepreneur and so much more. It’s hard to scratch the surface of the impact she has had on me forever.”

The couple welcomed their first child together, daughter Eliyanah, in 2020. After Diana joined the RHOBH cast in season 12, she revealed during a June 2022 episode that she and Monroe — who have a 15-year age gap — were engaged after a decade of dating.

In a separate episode that same month, Diana opened up about experiencing a pregnancy loss after conceiving her second child with the singer.

Speaking to costar Kyle Richards, the Bravo star personality that she found out she was pregnant again less than six months after Eliyanah’s birth. A consultation with her doctor revealed a complication, and Diana had to deliver the stillborn baby in order to avoid a possibly dangerous infection.

Six months later, Diana confirmed she and Monroe were expecting a rainbow baby while replying to a fan via Instagram.

 “🙏🙏🙏🙏 Long way to go but thank you,” she wrote in the comments section of a video showing off her elaborate holiday decor.

RHOBH costar Kathy Hilton also gave her congratulations, writing, “Congratulations!!!!❤️.” Diana replied with three red heart emojis.

Later that day, the Room 23 author shared a glimpse of her fiancé playing with their daughter. “@ashermonroe Christmas is here to stay 😊🎄🎅🎉🎄,” she captioned the sweet footage of Monroe spinning around with the toddler on his back.

Keep scrolling to relive the twosome’s romance:

The pair met while separately attending a Victoria’s Secret fashion show. 

The reality star and Monroe began dating and the pair founded the independent music label D Empire Entertainment together. 

Diana and the “Try” singer welcomed their first child together, daughter Eliyanah. 

“Thank you 2020 😊 Happy New Year everyone 🎊🎈 🎉,” Diana wrote via Instagram on December 31 alongside a sweet video of Monroe and their newborn. 

Monroe praised Diana during an interview with Pop Hearts TV after being asked who had made a valuable impact on his career.

“[Diana] has stood by my side through thick and thin,” he gushed. “Without her, I would not be the man I am today. I have always looked up to her in the way she runs her life. Being a role model, war survivor, philanthropist, mother, entrepreneur and so much more. It’s hard to scratch the surface of the impact she has had on me forever.”

The musician took to social media to share a heartfelt tribute to the former model on Valentine’s Day. 

“Happy Valentines my Angel @sdineuro. I still can’t believe this March will be 12 years since I first laid eyes on you,” he captioned a carousel of images of the twosome together. “It feels like a flash from all the wild and crazy fun. If it was only highs, it wouldn’t be real, if it were only lows we’d never know … it’s experiencing true love. In this life that has nourished my soul.”

The entrepreneur revealed during an episode of Real Housewives of Beverly Hills that she found out she was pregnant again — less than six months after Eliyanah’s birth. After meeting with her doctor, who found a complication with the reality star’s pregnancy, Diana had to deliver a stillborn baby in order to avoid a possibly dangerous infection.

In a separate episode that same month, Diana mentioned that she and Monroe were engaged. 

The singer gave his love a shoutout on his birthday. 

“I might just be the luckiest man on earth. So grateful for another year I get to play this game of life and experience every blessing that’s unveiled on the daily,” Monroe wrote alongside a sweet snap of the pair with their infant. “Thank you for all the love and support from my family to yours.”

The Bravo star replied to an Instagram user who wished her well after Page Six reported that she was pregnant on December 9. 

“🙏🙏🙏🙏 long way to go but thank you,” she wrote in the comments section of a video showing off her elaborate holiday decor.

In response, the fan encouraged her to take the experience “one day at a time.”

Later that day, Diana shared a glimpse of her fiancé playing with their toddler. “@ashermonroe Christmas is here to stay 😊🎄🎅🎉🎄,” she captioned the sweet footage of Monroe spinning around with their daughter on his back.