Ben Affleck and Ana de Armas's Relationship Timeline: A Look Back

Bennifer might have made its return when Oscar-winning actor Ben Affleck and Jennifer Lopez reunited and married in two wedding ceremonies in 2022. However, he and Blonde star Ana de Armas were one of the hottest couples who quarantined together. 

After meeting in late 2019, before the pandemic, the pair were repeatedly photographed together on walks with their dogs. Affleck and de Armas tried to keep their relationship private, but when that didn't work, People reported that Affleck pranked the paparazzi by placing a cardboard cutout of the actress in front of his house.

Although they parted ways in 2021, just over a year into their relationship, Affleck and de Armas still shared many milestones, from romantic getaways — during which Affleck was a great Instagram boyfriend — to meeting each other's families. Despite rumors of a reconcilation, the Cuban actress confirmed via Instagram Stories that she and her Deep Water co-star were not getting back together.  

Here's a look back at Ben Affleck and Ana de Armas's relationship.

Late 2019: Ben Affleck and Ana de Armas first meet

Affleck and de Armas met on the set of the psychological thriller Deep Water in New Orleans. In the film, the two star opposite each other as husband and wife.

There aren't many details on exactly how the romance blossomed, but the actors reportedly were 100 percent professional on set.

"Ben always seemed very relaxed and happy around Ana, but at the time, there were no signs of romance," a source told People in 2020. "He was very focused on making a fantastic movie. He arrived early and was one of the last people to leave."

Regardless, the relationship seemed to move quickly, with Affleck and de Armas going from co-stars to quarantine buddies in almost no time.

March 2020: Ben Affleck and Ana de Armas vacation together

The two took a trip to the Knives Out star's native Cuba together. A source revealed to People that de Armas was excited to show her boyfriend around. (It helps that Affleck is fluent in Spanish.)

"Ben and Ana had a great time in Havana," an insider said. "Ana was his tour guide and took him to all her favorite places. Ben seemed to love the trip. He was in a great mood and very friendly. He was approached by fans multiple times and happily posed for pictures. They visited several restaurants and enjoyed Cuban cuisine."

Affleck's ex-wife, Jennifer Garner, was also "happy" for the couple. 

"Jen has completely moved on from Ben in a romantic sense. She considers him a friend, thinks he is a good dad to their children, and respects him," a source told Us Weekly. "She is happy in her own life and supportive of him and happy for him and his relationship."

April 30, 2020: Ben Affleck and Ana de Armas go Instagram official

Affleck and de Armas went Instagram official as they celebrated her 32nd birthday.

Just a few weeks before de Armas posted her PDA-filled photos on social media, a source shared with People: "They seem to have a great time together. They order delivery food and groceries and only leave the house for walks around the neighborhood with their dogs. Ben looks incredibly happy. They are flirty and goofy. Ana always has a huge smile around him."

A source also noted that de Armas and Garner were "friendly." 

"They haven't all hung out with the kids as one big group. Jen is not there yet," a friend of the couple told Us Weekly. "There is no doubt that they will do dinners and hangouts with the kids when Jen is ready, but no one is pressuring her to jump into that."

May 14, 2020: Ben Affleck and Ana de Armas make a cameo in a music video

Affleck and de Armas were one of many kissing couples featured in Residente's "Antes Que el Mundo Se Acabe" music video in May 2020.

Aside from the two actors, the visual featured celebrities such as Bad Bunny, Ricky Martin and husband Jwan Yosef, and Zoe Saldaña. "More than 100 kisses around the world," read the video description.

According to Us Weekly, de Armas couldn't stop expressing her admiration for Affleck at the time. 

"They are having so much fun together, and she has been telling her friends how Ben is the most amazing boyfriend she's ever had."

June 2020: Ben Affleck introduces Ana de Armas to his mother and three kids

In June 2020, the couple attended a Black Lives Matter protest together in Los Angeles. The Argo star was photographed with a sign reading "Black Lives Matter." 

"Ben wants to continue to be a model for his children. They talk about these important issues," a source told People.

Later that month, Affleck and de Armas took a family vacation with Affleck's mother, Christine Boldt, children, and dogs, per People. 

"They are spending a few days in Georgia with Ben's kids. It's a low-key vacation," a source said. "Ana seems to love being around his kids. Everyone has been getting along great. Ana is making an effort to get to know his kids."

August 2020: Ben Affleck and Ana de Armas go on a double date

The Ghosted actress and her beau were spotted on a double date with Affleck's BFF, Matt Damon, and his wife, Luciana Barroso, in Malibu.

According to Us Weekly, Affleck was committed to making de Armas as happy as possible. 

"Ben is so sweet to Ana and does everything he can to make her happy," a source said. "She can say anything — lunch, trips, etc. and he will make it happen."

E! Online noted that de Armas's low-key lifestyle was key to the Gone Baby Gone director maintaining his sobriety. 

"Since Ana has been in Ben's life, being sober has become easier to manage," a source said. "She came into his life and has given him everything he wants and needs in a partner. He's very satisfied with Ana and isn't looking for a coping method. She has a vivacious personality and is a very talented actress."

Since they got together, the source said Affleck had been much more comfortable with staying at home (though the COVID-19 quarantine certainly may have had something to do with that). 

"Drinking isn't part of the equation with Ana," the source continued. "She's very supportive, and she doesn't party or make alcohol a big part of her life. It's not what they do as a couple or a part of their relationship. He really hasn't felt the want or need since they have gotten into a relationship."

Reports circulated that the two were maybe moving in together — a major move, indeed — after de Armas was seen bringing some of her belongings into Affleck's home. 

"She had a huge grin and seemed very excited about living with Affleck," a source told People. De Armas also gifted her boyfriend a custom BMW motorcycle for his 48th birthday.

Another source added, "Ben and Ana really care for each other, and they have a good thing going. She's aware that his family comes first. And appreciates that. They work very hard at that balance."

January 2021: Ben Affleck and Ana de Armas break up

People confirmed de Armas ended the relationship in 2021, citing geography as the primary reason for the split. 

"Ben is no longer dating Ana," a source revealed. "She broke it off. Their relationship was complicated. Ana doesn't want to be Los Angeles-based, and Ben obviously has to since his kids live in Los Angeles."

Another source added, "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. Ben continues to want to work on himself. He has three jobs lined up, and he’s a solid father at home. They are both happy with where they are in their lives."