When Ana De Armas and Tom Cruise were seen grabbing dinner together on Valentine’s Day, it sparked a whirlwind of rumors that the two stars were dating.
Many wondered if Tom, 62, had finally found love again with Ana, 36, following his highly publicized split from Katie Holmes.
As for Ana, some took the outing as confirmation that her controversial romance with Manuel Anido Cuesta had come to an end.
The actress was first linked to Manuel, the stepson of Cuba’s president, last November, and immediately, the Knives Out star, who had fled Communist Cuba at age 18, faced scrutiny over the romance.
But Ana seemed to put the speculation over her and Tom’s date night to rest when she was spotted cozying up to Manuel again on Monday.
Her night out with Tom followed by her intimate stroll with Manuel raised many questions about her love life – and this certainly isn’t the first time that Ana has made headlines thanks to her romantic entanglements.
Over the years, she’s been linked to a slew of high profile men including a few actors, a tech mogul, and an acclaimed Hollywood talent agent.
Arguably her most famous relationship was with Ben Affleck, who she dated between his split from Jennifer Garner and his whirlwind reconciliation with Jennifer Lopez.
As Ana raises eyebrows thanks to her outing with Tom, take a look inside her rollercoaster ride love life.
Marc Clotet
Ana met Spanish actor and model Mac Clotet in 2010, while she was an up and coming actress living in Spain. They’re seen together in September 2011
They wed in July 2011 during a private ceremony in Costa Brava, Spain, but they split in 2013 after two years of marriage. They’re seen in December 2011
It’s unclear what lead to their breakup, but Ana moved to Los Angeles soon after to focus on starring in American shows and movies. She and Marc are seen in September 2011
Ana met Spanish actor and model Mac Clotet in 2010, while she was an up and coming actress living in Spain.
Marc is best known for his roles in the soap opera El cor de la ciutat and the drama series Física o química.
They wed in July 2011 during a private ceremony in Costa Brava, Spain, but they split in 2013 after two years of marriage.
It’s unclear what lead to their breakup, but Ana moved to Los Angeles soon after to focus on starring in American shows and movies.
Franklin Latt
After her divorce and move to the states, Ana started dating Hollywood talent agent Franklin Latt (seen in 2017)
They got together in 2015 and became engaged soon after. But Ana and Franklin, who manages Pedro Pascal, called off the wedding and went their separate ways less then a year later
After her divorce and move to the states, Ana started dating Hollywood talent agent Franklin Latt.
They first got together in 2015, right after her Hollywood breakout role in the Keanu Reeves-led flick Knock Knock.
The two became engaged soon after, but they called off the wedding and went their separate ways less then a year later.
Franklin now works for Creative Artists Agency (CAA) and currently manages actor Pedro Pascal.
Alejandro Piñeiro Bello
Ana was linked to Cuban artist Alejandro Piñeiro Bello in 2017. As she began rising at a Hollywood starlet, he was usually spotted by her side at events. They’re seen in 2018
They were together for two years before they broke up in 2019
Ana was linked to Cuban artist Alejandro Piñeiro Bello in 2017.
As she began rising at a Hollywood starlet, he was usually spotted by her side at events and often popped up on her social media accounts.
They were together for two years before they broke up in 2019.
Ben Affleck
Ana met Ben Affleck on set of the thriller Deep Water in 2019. Soon after, rumors began to erupt that they were dating after they were spotted on vacation in Cuba together (seen)
They then confirmed that they were indeed a couple when they were spotting kissing in March 2020 (seen), and by April 2020, they were Instagram official
Ana met Ben on set of the thriller Deep Water in 2019, in which they played husband and wife.
Soon after, rumors began to erupt that they had taken their love off screen and into real life after they were spotted on vacation in Ana’s home country Cuba together.
At the time, Ana posted a loved-up selfie of her and Ben, in which he placed his hand tenderly on her stomach
They then confirmed that they were indeed a couple when they were spotting kissing in March 2020, and by April 2020, they were Instagram official.
At the time, Ana posted a loved-up selfie of her and Ben, in which he placed his hand tenderly on her stomach.
That June things heated up as she jetted off on vacation with him, his kids, and his mother in Georgia.
They spent much of 2020 inseparable, enjoying walks in LA with their dogs and casual outings for coffee.
But in January 2021, news broke that the couple had called it quits.
‘Ben is no longer dating Ana. She broke it off. Their relationship was complicated,’ a source told People at the time.
‘Ana doesn’t want to be Los Angeles-based, and Ben obviously has to since his kids live in Los Angeles.’
They spent much of 2020 inseparable, enjoying walks in LA with their dogs and casual outings for coffee
But in January 2021, news broke that the couple had called it quits
Another insider dished, ‘This is something that was mutual and something that is completely amicable.
‘They are in different points in their lives; there is deep love and respect there.’
Ana – who moved to Vermont in 2023 – later spoke of the highly publicized relationship to Elle, calling all the attention they received ‘horrible.’
‘That’s one of the reasons why I left LA,’ she shared.
‘This is not the place for me to be,’ she added of LA. ‘It became a little bit too much. There’s no escape. There’s no way out.’
Paul Boukadakis
In June 2021, it was revealed that Ana had been ‘quietly seeing’ Tinder Vice President Paul Boukadakis. They’re seen in September 2022
While they kept the details of their romance mostly out of the spotlight, they were spotted packing on the PDA on multiple occasions over the next few years. They’re seen in 2022
In June 2021, it was revealed that Ana had been ‘quietly seeing’ Tinder Vice President Paul Boukadakis.
‘Paul and Ana were introduced through friends,’ a source told Page Six at the time.
‘He has been spending a lot of time with Ana before she left the US to film her new movie.’
While they kept the details of their romance mostly out of the spotlight, they were spotted packing on the PDA on multiple occasions over the next few years.
It’s not known when exactly they went their separate ways, but in November 2024, she was spotted smooching Manuel, seemingly confirming that she and Paul had ended their romance.
Manuel Anido Cuesta
It’s not known when exactly they went their separate ways, but in November 2024, she was spotted smooching Manuel Anido Cuesta (seen)
The actress faced immense scrutiny online over the relationship at first. But they did not let the public outrage stop them from stepping out together for a loved-up stroll in Madrid weeks later
Ana and Manuel, who is the stepson of Cuba’s president, made headlines when they were photographed kissing during a night out in Madrid, Spain, in November 2024.
The actress faced immense scrutiny online over the relationship at first.
She was savaged by her compatriots and others who accused her of dating the son of a dictatorship that she fled from.
But they did not let the public outrage stop them from stepping out together for a loved-up stroll in Madrid weeks later.
The couple held hands and looked perfectly in sync in similar outfits as they went for a walk together in mid-December.
Ana has stayed tight lipped on the romance, but many people took her Valentine’s Day outing with Tom as a sign that she and Manuel had split.
However, she and Manuel were seen together again in Madrid on Monday, so it seems their relationship isn’t over.
The Knives Out alum was photographed linking arms with her lawyer beau as they enjoyed a hot drink together.
Tom Cruise
Ana sparked romance rumors with Tom Cruise this weekend as they put on a close display after enjoying dinner together on Valentine’s Day
But Ana seemed to put the speculation over her and Tom’s date night to rest when she was spotted cozying up to Manuel again on Monday (seen)
Ana and Tom put on a close display as they were spotted out in Soho, London, for dinner together on Valentine’s Day.
The Mission Impossible star and the Cuban-born actress were mobbed by fans during their evening out and stopped to take pictures as a crowd formed around them.
The A-list pairing put on animated display and carried two bags of takeaway food on their way out of the restaurant, before hopping into a taxi together.
