Kaley Cuoco’s Journey Through Love: From Secret Romances to Third Engagement

Emmy-nominated actress Kaley Cuoco, 38, has built an impressive career in Hollywood, captivating audiences in beloved shows like 8 Simple Rules, the iconic The Big Bang Theory, and the critically acclaimed The Flight Attendant. Beyond her professional successes, Cuoco has frequently made headlines for her vibrant and often-talked-about love life. The California native has experienced the highs and lows of romance, including two previous marriages: her first to tennis player Ryan Sweeting, 37, from 2013 to 2016, and her second to equestrian Karl Cook, 33, which lasted from 2018 to 2021.

Following her second divorce, Cuoco candidly shared in an April 2022 interview with Glamour that she would “never get married again,” a sentiment many could understand after two high-profile separations. However, love, as it often does, had other plans. Just two years into her relationship with actor Tom Pelphrey, Kaley surprised fans by announcing her engagement, sharing a joyous image of a ring adorning her finger—a significant moment that marks a new chapter in her personal life, especially as they welcomed their daughter, Matilda, earlier this year. This latest development underscores a remarkable evolution in her perspective on love and commitment.

Join us as we delve into the full story of Kaley Cuoco’s dating history, exploring the relationships that have shaped her journey to finding happiness.

Kevin Zegers

One of Kaley’s early public relationships was with Canadian actor Kevin Zegers, 39. The pair first crossed paths in 2003 on the set of the horror film The Hollow, where their on-screen chemistry reportedly blossomed into a real-life romance. They dated for approximately a year, a formative period in Kaley’s budding career. Kevin, known for his roles in the beloved Air Bud film series and his memorable portrayal of Damian Daalgard in the hit series Gossip Girl, has also found lasting love. He married talent agent Jaime Feld in 2013 after six years of dating, and the couple welcomed twin girls, Zoe Madison and Blake Everleigh Zegers, two years later, building a beautiful family life together.

Thad Luckinbill

In 2004, Kaley had a brief romance with actor Thad Luckinbill, 49. Interestingly, their connection predated their personal relationship, as Thad had made several guest appearances on Kaley’s show 8 Simple Rules, playing Donny Doyle, a love interest for Kaley’s character, Bridget Hennessy. Thad is perhaps most recognized for his long-running role in the iconic CBS soap opera The Young and the Restless, where he starred for over a decade. His personal life also mirrors a successful trajectory; he married his The Young and the Restless co-star, Amelia Heinle, in 2007, and the couple has since welcomed two children, establishing a family deeply rooted in the world of daytime television.

Jaron Lowenstein

Between 2005 and 2006, Kaley’s romantic interest shifted to country singer Jaron Lowenstein, 50. Jaron was a part of the popular musical duo Evan and Jaron, alongside his twin brother. While their music career saw significant success in the early 2000s, Jaron hasn’t released new music since 2010. He humorously describes himself as a two-time “one-hit-wonder” in his Instagram bio, reflecting on his past achievements with a touch of self-deprecating charm. Despite his public profile, Jaron appears to be focused on his family life. He does not seem to be married but is a devoted father to two young children, Poppy and Beckley, whom he adores. In November 2020, he shared a heartwarming post on Instagram celebrating Poppy’s second birthday, sweetly writing, “Happy birthday to my little 2 year old singer, Poppy. Jury is still out on whether her 7 month old sister (Beckley) has any talent but she’s a good listener. I love my kids so much. I’m not saying they’re the cutest kids ever, but they’re definitely not the ugliest. Hashtag blessed.” This glimpse into his personal life shows a man enjoying fatherhood and appreciating his children.

Al Santos

In 2007, rumors circulated about a possible romance between Kaley and actor-producer Al Santos, 48. However, their relationship was never officially confirmed by either party, remaining largely speculative. Al Santos is primarily recognized for his role in the 2001 TV series Grosse Pointe, a satirical look at teen dramas. While the details of their alleged connection remain elusive, it highlights the growing public interest in Kaley’s personal life as her career continued to gain momentum.

Josh Henderson

Another unconfirmed but widely reported romance for Kaley was with actor Josh Henderson, 42. Like Al Santos, neither Kaley nor Josh publicly confirmed their relationship. Although Josh had appeared on 8 Simple Rules with Kaley back in 2002, dating rumors didn’t begin to circulate until 2007. Josh Henderson has an extensive acting resume, with notable credits including the popular TV series Desperate Housewives, The Arrangement, and the revival of Dallas. Their rumored relationship underscores a period in Kaley’s life where her personal connections often remained private, even amidst growing media speculation.

Johnny Galecki

Perhaps Kaley’s most famous and beloved relationship was with her The Big Bang Theory co-star, Johnny Galecki, 49. The two played the iconic on-again-off-again couple, Leonard and Penny, for all 12 seasons of the hit show. What many fans didn’t know at the time was that their on-screen romance mirrored a real-life relationship between 2007 and 2009, which they meticulously kept under wraps. “It was such a huge part of my life, and no one knew about it,” Kaley revealed in an interview with CBS Watch (via Today). “It was a wonderful relationship, but we never spoke a word about it and never went anywhere together.” The secrecy added a unique layer to their dynamic, both personally and professionally.

Years later, in 2019, Kaley openly discussed their past relationship, confirming that despite the breakup, there were never any lingering bad feelings, and their separation was mutual and amicable. “Johnny and I were friends first, then obviously we dated. When we broke up, it was funny because that was when our relationship on the show was hot and heavy. There were a lot of bed scenes. We were a little like, ‘We were trying to end the relationship and it kept falling back in,’” she humorously recalled to Haute Living. “We got over it really fast, and we’re closer than ever now. It could have gone either way, and I was really proud of us.” Their ability to maintain a strong friendship and professional collaboration after their romance ended is a testament to their maturity and mutual respect, solidifying their bond both on and off screen.

Josh Resnik

Following her relationship with Johnny Galecki, Kaley briefly entered a new phase of her love life with addiction specialist Josh ‘Lazie’ Resnik. Very little is publicly known about their relationship, which highlights Kaley’s ability to keep certain aspects of her private life out of the public eye when she chooses. The main known facts are that they dated, got engaged in October 2011, but then called off the engagement a short time later. No specific details were ever provided regarding the reasons behind their split. This brief engagement marked an early instance of Kaley’s willingness to consider marriage, even if it didn’t ultimately lead to the altar at that time.

Christopher French

After her engagement to Josh Resnik ended, Kaley moved on with actor and Annie Automatic musician Christopher French, 42. Their relationship spanned from 2011 to 2012, a period during which they publicly supported causes close to their hearts. In a heartwarming video they created for the Humane Society, Kaley affectionately referred to Chris as her “incredible boyfriend.” The video also featured their musical talents, with Kaley singing and Chris playing the guitar in their rendition of “Somewhere Over the Rainbow.” Beyond his artistic endeavors, Chris is widely known as the husband of former Disney Channel star Ashley Tisdale, 39. The couple tied the knot in 2014 and expanded their family by welcoming a daughter named Jupiter Iris in 2021. Chris frequently expresses his profound love for his family, sharing sweet tributes on social media. On Valentine’s Day 2022, he posted on Instagram, “Happy Valentine’s Day to the 2 loves of my life. I still can’t believe I get to call them my forever valentines. I’m so lucky,” alongside a photo of Ashley holding Jupiter, illustrating the deep affection he holds for them.

Bret Bollinger

Kaley’s pattern of dating musicians continued as she became romantically involved with Pepper band member Bret Bollinger, 46, from 2012 to 2013. Their relationship gained public attention when they were photographed engaging in public displays of affection (PDA) at a Lakers vs. Trailblazers basketball game in Los Angeles in March 2012, effectively confirming their romance. Bret, known for his role as the singer and bassist for the reggae rock band Pepper, remains an active musician, continuing to tour with his band. As of current reports, he does not appear to be in a public relationship, maintaining a focus on his music career. This relationship provided another glimpse into Kaley’s varied romantic interests and her enjoyment of the company of creative individuals.

Henry Cavill

In July 2013, Kaley Cuoco had a very brief, yet highly publicized, romance with real-life Superman, actor Henry Cavill, 41. Their relationship, though lasting only about ten days, garnered immense media attention, largely due to Cavill’s rising global fame from his role in Man of Steel. The sudden spotlight proved overwhelming for Kaley, making their short-lived relationship quite stressful. “I had no one following me until I met Superman,” the Big Bang Theory star confided to Cosmopolitan in 2014. “I’ve been in this business for 20 years, and my whole life, I could go anywhere, do anything. There had not been one paparazzi photo of me until like several months ago. The recognition was crazy.” This experience highlighted the intense scrutiny that comes with dating a global superstar, a level of fame Kaley hadn’t fully encountered before. Henry Cavill has since moved on and is in a committed relationship with Natalie Viscuso. He publicly confirmed their romance in a May 2021 Instagram post, addressing some “animosity” he noticed on his feed regarding his relationships and asking for positivity. “Let’s embrace this age of social enlightenment together, and move forward with positivity. I am very happy in love, and in life,” he shared alongside a selfie with Natalie. “I’d be enormously grateful if you were happy with me. If you can’t bring yourself to be happy with me, then at the very least try to do yourself proud and be the best version of yourself.” Natalie is often seen as his staunch supporter, frequently featured on his social media.

Paul Blackthorne

In 2015, approximately three months after filing for divorce from her first husband, Ryan Sweeting, Kaley began seeing British actor Paul Blackthorne, 55. Their relationship was subtle, but Kaley subtly confirmed it through her actions and social media. In November of that year, she shared a snapshot of herself wearing a t-shirt designed to support Paul’s conservation charity, Air Shepherd. “Help my friend @paulblackthorne @airshepherd #KeepRhinosHorny,” she wrote, giving a thumbs up to the camera. Paul Blackthorne is widely known for his roles in popular TV series such as Arrow, where he played Quentin Lance, and The Dresden Files. This relationship demonstrated Kaley’s support for her partner’s passions, even as she navigated a significant life transition.

Tom Pelphrey

Kaley Cuoco’s romantic journey found a new and joyous direction with actor Tom Pelphrey, 42. Their relationship became public in May 2022 when Kaley shared a carousel of PDA-filled pictures on Instagram, including heartwarming snapshots from a mountain getaway. “Life lately… ‘the sun breaks through the clouds, rays of gold slipping into my eyes and heart, rays of yellow to break the grey,’” she captioned the photos, one of which beautifully captured Tom tenderly kissing her on the cheek. This post marked a significant moment, signifying a deep and affectionate connection that was quickly embraced by fans.

Tom Pelphrey, an accomplished actor, is celebrated for his compelling performances in soap operas like Guiding Light and As the World Turns, where he earned critical acclaim. More recently, he gained widespread recognition for his powerful portrayal of Ben Davis in the Netflix original series Ozark, showcasing his versatility and depth as an actor. His talent and grounded nature seemed to resonate deeply with Kaley, leading to a profound partnership.

Their relationship quickly blossomed, bringing immense joy and a new chapter to Kaley’s life. In a heartwarming turn of events, Kaley Cuoco and Tom Pelphrey welcomed their daughter, Matilda Carmine Richie, into the world in March 2023, making them proud parents and solidifying their family unit. This beautiful addition marked a pivotal moment, filling their lives with even greater happiness and purpose.

Adding another layer of excitement, Kaley confirmed on August 15, via her Instagram Stories, that she is officially engaged to Tom Pelphrey. Sharing a radiant photo that proudly displayed her engagement ring alongside the actor, she captioned it, “Amazing weekend,” a simple yet profound statement reflecting their shared joy and anticipation for the future. This engagement, coming after her previous statements about not remarrying, speaks volumes about the genuine connection and deep love she shares with Tom, proving that sometimes, life’s most beautiful plans are the ones you never expected.

Kaley Cuoco’s path to love has been a public and often winding one, filled with memorable relationships, both fleeting and long-lasting. From early co-star romances to brief flings and two marriages, each chapter has undoubtedly contributed to her growth and understanding of what she truly seeks in a partner. Her journey culminates in a joyous engagement to Tom Pelphrey, with whom she shares a beautiful daughter, Matilda. This new beginning signifies not only a commitment to a loving partner but also a profound sense of contentment and happiness in her personal life, demonstrating that true love can indeed find you when you least expect it, reshaping your perspective and bringing unexpected blessings.