Why Ben Affleck Was Ready For Another Chance at Love

Mere weeks after Ben Affleck revealed he was on the hunt for a "deeply meaningful" relationship, he's romancing Deep Water costar Ana de Armas all the way from Cuba to California.

By Sarah Grossbart Aug 15, 2020 7:00 AMTags
Watch: Ben Affleck & Ana de Armas Are Instagram Official!

Ben Affleck is not the type to swipe right. Or left. 

Sure, he'd been actively dating since his April 2019 split with girlfriend Lindsay Shookus, their second stab at romance never getting fully off the ground. He'd even spent some time with musician Katie Cherry in the back half of 2019. But he wasn't exactly trolling for love on the Internet. 

"I am on no dating [apps]. No Tinder. Grindr. Bumble. Humble. I am not on any of them," The Way Back actor told Diane Sawyer in a February Good Morning America interview, part of a press push that saw him open up on everything including his divorce from Jennifer Garner ("The biggest regret of my life,") to his ongoing treatment for alcoholism. "I don't have judgment for people who are, great. I know people who are on them and have a fun time but that's not me."

Ben Affleck: Movie Star

An office romance is much more his style. 

Though he and Deep Water costar Ana de Armas  only just began dating this past spring—a loved up March trip to her native Cuba served as their unofficial coming out party—pals are already labeling the partnership a success, noting the actress' commitment to supporting Affleck's continued sobriety and her all-around caring nature. "Everything seems to work between them," one insider told E! News, "and it's been a long time since he has fallen hard like this."

And the father of Violet, 14, Seraphina, 11, and Samuel, 8, has made it clear his end goal is to find a forever type of romance. "I would love to have a relationship that is deeply meaningful," the 48-year-old told Sawyer, "and one to which I could be deeply committed."

@Luz_Cuba Twitter

To those on the New Orleans set of their psychological thriller, it was instantly clear it could be with 32-year-old de Armas, an actress who earned a Golden Globe nod for her turn in 2019's Knives Out. "They had great chemistry right from the start," a source told People of the pair who play husband and wife in Deep Water, currently set for a November release. 

But if the National Theater School of Cuba alum seemed transfixed during filming, it was with the two-time Oscar winner's talent. "The first time we read the scenes together, it became pretty clear he was going to do something exceptional with a very complex role," de Armas told Vogue Spain in March. "His character is the engine of the story and requires him to move between tragedy and irony or between realism and the most absurd comedy."

Continued the actress, who shot to fame as part of the Spanish drama series El Internado, "Not only does he know how to do it with ease, he also manages to surprise you in every shot."


Affleck's affable charm is the stuff of legends as well. But an insider insists the two honed in on constructing their onscreen relationship rather than any personal one. 

"Ben always seemed very relaxed and happy around Ana, but at the time there were no signs of romance," the set source told People. "He was very focused on making a fantastic movie. He arrived early and was one of the last people to leave."

Still, the star of the upcoming Bond film No Time to Die proved intriguing. And since she'd been striking out on finding a suitable partner in Hollywood ("I've had company here, but it's been the wrong company so I prefer to be alone," she recently griped to Vanity Fair), it seemed worthwhile to at least explore what could take place between them after their months of filming wrapped in February. 

Stoianov-spot / BACKGRID

Traveling to the actress' native Havana, they frequented stores, restaurants and the Cuban Art Factory, a cooking oil factory turned nightclub, art exhibit and eatery. "Ana was his tour guide and took him to all her favorite places," a source told People, adding that Affleck, who mastered Spanish while filming a children's TV show in Mexico as a teen, "seemed to love the trip. He was in a great mood and very friendly."

The good times continued with a jaunt to Costa Rica (where his pals Tom Brady and Gisele Bündchen happen to own a place, FWIW) that saw the costars mainly relaxing at their rental's beach, emerging for sunset walks with a healthy serving of PDA. 

"They have been kissing, cuddling up together and putting their arms around each other a lot," an onlooker told E! News. "They look at each other adoringly and like taking pictures of each other."

Between all the selfies and the giggles, it's clear to see that Affleck is smitten. "Ben seems blissfully happy and giddy. He can't stop smiling and laughing," continued the onlooker. "They are without a doubt a couple."

Jennifer Garner & Ben Affleck: Romance Rewind

That became even more evident when they returned stateside, the stay-at-home restrictions affording plenty of time to build on an already exciting romance.

Largely quarantined together at his Los Angeles home, "They have a simple daily routine," a source told E! News, that revolves around ordering food from Postmates and taking the actress' dogs, Elvis and new pup Salsa, for walks—outings that have only served to outline just how well their quarantine experience is going. 

Stoianov / BACKGRID

"Ben and Ana look like total lovebirds. They laugh together and share funny stories," continued the source. "She is very nurturing and he seems to love that. They can't get enough of each other. After days of being quarantined and never leaving each others' sides, they are still laughing, smiling, kissing and hugging."

Their only separations have come on the days when Affleck visits with his kids; though, as they've grown more serious, de Armas has tagged along for a few of those as well. "Ana loves kids and couldn't wait to meet them and spend time with them," the insider explained. "She knows how much they mean to Ben and so she was anxious to be a part of that." 

And, as evidenced by the kids' de Armas-related practical joke, the encounter went quite well. "She is very sweet and kind to the kids," noted the insider. "They immediately warmed up to her and like her a lot. They are all comfortable together and she's very nurturing. Everything has worked out very well."

Just in time for Affleck to celebrate his 48th birthday today, an occasion de Armas will no doubt make special after his showing on her April birthday that involved a private getaway, a piñata and more than a few balloons. "She is loving, caring and fun," the insider told E! News of de Armas. "They are always laughing and making each other smile. Ben is extremely happy with her."

And should their coupling continue on its upward trend, that would fit in nicely with Affleck's current life plan. 

"Five years from now Ben Affleck is sober and happy and sees his kids three-and-a-half days a week and has made three or four movies that are interesting to him," he predicted on Good Morning America. "[And] directed two [movies] that he is hopefully proud of and is in a healthy, stable, loving, committed relationship."

(Originally published March 17, 2020 at 3 a.m. PT)