Dating History: From Tom Cruise to Ben Affleck in Hollywood

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The Cuban-American actress Ana de Armas gained significant recognition following her captivating performance in the 2019 film Knives Out, where she portrayed a sweet and devoted housekeeper embroiled in a murder mystery surrounding a wealthy patriarch. This role not only showcased her immense talent but also catapulted her into the spotlight, attracting the attention of media and fans alike. With newfound fame comes an intense curiosity about one’s dating history, and Ana’s romantic life became a focal point, especially following her high-profile relationship with Ben Affleck. The press’s scrutiny of her personal life intensified, leading to widespread interest in her relationships.

Since parting ways with Ben, Ana de Armas has opted for a more private approach to her romantic life. She is currently in a relationship with a tech CEO who is the mastermind behind the video-sharing app, Wheel, which has recently been acquired by Tinder. Prior to her relationship with her entrepreneurial partner and her time with Ben Affleck, Ana had a history of dating several accomplished men and was even married at one point. Continue reading to discover more about Ana de Armas‘ dating history, including her rumored connections with Tom Cruise.

Unveiling the Relationship Rumors Between Ana de Armas and Tom Cruise

The sparks of romance between Ana de Armas and Tom Cruise first ignited in February 2025, as the two were spotted together on various friendly outings that hinted at a potential relationship. After several months of speculation and dodging inquiries from the media, the pair was finally seen enjoying a low-key date in Vermont, where they were caught on camera holding hands, as reported by TMZ. This public display of affection fueled further rumors about their romantic involvement, drawing attention from fans and entertainment news outlets alike.

The Romance Between Ana de Armas and Paul Boukadakis: A Closer Look

Ana de Armas and the Tinder executive Paul Boukadakis were romantically linked from 2021 until 2024. Sources revealed that the couple was introduced through mutual friends, and Paul, who resides in Austin, Texas, was frequently shuttling between his home state and Santa Monica to be with Ana. Reports indicated that he had introduced Ana to some of his family members during their relationship, which had been blossoming for several months by that time. Their relationship was characterized by shared experiences and a growing bond, marking a significant chapter in Ana’s dating history.

The couple reportedly lived together in New York City, as stated by Elle. One of the pivotal factors that contributed to Ana’s breakup with Ben was her desire to avoid being permanently based in Los Angeles, especially given the intense public scrutiny surrounding their relationship. Reflecting on her feelings about the City of Angels, Ana expressed to Elle, “Going through it confirmed my thoughts about, ‘This is not the place for me to be.’ It became a little bit too much. There’s no escape. There’s no way out.” She continued, explaining how the city made her feel perpetually anxious, highlighting her struggles with the overwhelming nature of fame.

Very little is known about Paul Boukadakis outside of his professional achievements, as he maintains a low profile without an active Instagram account, and his Twitter account is set to private. Professionally, he became a vice president at Tinder following the acquisition of his video-sharing app, Wheel. According to his LinkedIn profile, Paul attended Loyola Marymount University and grew up in Tulsa, Oklahoma, where he graduated from Bishop Kelley High School, as mentioned in a 2016 interview with Entrepreneur.

The High-Profile Romance of Ana de Armas and Ben Affleck

Ana de Armas first crossed paths with Ben Affleck while filming the psychological thriller Deep Water, which premiered in March 2021. Their romantic relationship began in early 2020, and they made their official couple debut in March of that year during a romantic getaway to Cuba. Witnesses who encountered the couple in Cuba described them as visibly happy, with one observer noting, “They were beaming. I saw Ana grab Ben’s arm as they walked out together; they looked super happy — she’s absolutely stunning! I totally think they’re dating.”

Following their Cuban getaway, the affectionate couple was frequently seen in Los Angeles, particularly during the early stages of the coronavirus pandemic. They engaged in public displays of affection, whether it was strolling through Hollywood or shopping with Ben’s children, whom he shares with ex-wife Jennifer Garner. Their relationship also included a coastal vacation in Costa Rica shortly after their trip to Cuba, further solidifying their bond.

Regarding Ben’s children, a close source revealed to HollywoodLife EXCLUSIVELY in June 2020 that Ben introduced Ana to his kids with the blessing of Jennifer Garner. “He definitely didn’t just blindly introduce them and of course communicated with Jen on this before doing so. They co-parent really, really well still, and want the other to be happy,” the insider shared. “The kids see how much their dad likes her. He’s very happy and doing great. It’s been a slow process getting the kids involved with Ana, but so far they like her. They just want to see their dad happy.”

In December 2020, Ana made the significant decision to move into Ben’s Los Angeles home after selling her own property, as reported by PEOPLE. Unfortunately, their romance came to an end by January 2021. An insider explained, “The quarantine was unique because they had downtime and really got to know each other spending time at home. But once work picked up, things started to change.”

The insider added that Ana was uncomfortable with the idea of firmly establishing herself in LA. “She’s here for work reasons; like all actors, she lives wherever work takes her,” another source close to the actress stated. “Ana decided she doesn’t want to live in LA, and Ben wants to be close to his family,” another added. “His priority is to be rooted in LA. They are in different places.”

Exploring Ana de Armas’ Marriage to Marc Clotet

Ana de Armas was previously married to Spanish actor and model Marc Clotet from 2011 to 2013. Not much is publicly known about their marriage, as it took place before Ana achieved widespread fame in Hollywood. During their time together, she starred in the horror film Blind Alley, participated in two short films, and appeared in the Spanish series, Hispania, la leyenda, among various other projects listed on IMDb. Marc Clotet is recognized for his roles in notable films such as The Sleeping Voice (2011), La Estrella (2013), and The Chessplayer (2017).