Ben Affleck’s Relationship Timeline Explored

Ben Affleck is known for his high-profile relationships, but interestingly, he seems to have a type – people named Jennifer. He has been married to two different women named Jennifer. Additionally, he tends to date his co-stars, which is a common pattern in his romantic life.

As of July 16, he’s married to Jennifer Lopez. They started dating more than 20 years ago when they met while making the movie “Gigli.”

The actor has dated some of Hollywood’s most gorgeous ladies, so here’s a look back at his prior loves, from his high school sweetheart to his marriage to Jennifer Lopez and all the women in between.

Ben Affleck’s Relationship Timeline

1. Cheyenne Rothman

Ben Affleck and Cheyenne Rothman first met when they were teenagers at summer camp. They became sweethearts in high school and dated for more than seven years.

In those days, Ben was in high school at Cambridge Rindge and Latin High School in Massachusetts. Unfortunately, they decided to go their separate ways in 1997.

After their time together, Rothman became a film director.

Related: All the Movies Featuring Both Ben Affleck and Liv Tyler

2. Gwyneth Paltrow

Paltrow and Affleck were kinda together now and then between 1997 and 2000. At the same time, Paltrow was with Pitt from 1994 to 1997. Affleck got his first Oscar for Good Will Hunting in 1997 and became a big deal.

After winning the award, Paltrow was the first famous person Affleck was seen with. They met at a dinner thrown by Harvey Weinstein in 1997 (before he got in trouble), and they acted together in movies like Shakespeare in Love in 1998 and Bounce in 2000.

3. Jennifer Lopez

In early 2002, Jennifer Lopez and Ben Affleck met while making a movie called “Gigli.” Jennifer was already married to her second husband, Cris Judd. But by the middle of the year, Jennifer and Cris separated.

She even started the process to officially end their marriage two days after people saw her kissing Ben at her surprise 32nd birthday party. That was the first time they were seen as a couple.

In November 2002, Ben proposed to Jennifer when she visited his family in Boston. Jennifer shared this news during an interview with Diane Sawyer, when he asked her to marry him.

Unfortunately, by January 2004, it was reported that they were officially not together anymore.

4. Jennifer Garner

Although the former couple did not start dating until four years after they initially met on the Pearl Harbor set.

Affleck and Garner became close friends after they starred in the 2003 film Daredevil, and by the summer of 2004, their friendship had taken a romantic turn.

The couple welcomed three children after getting married in June 2005: a son named Samuel Garner and two daughters, Violet Anne and Seraphina Rose Elizabeth.

April 13, 2017, Affleck and Garner filed for divorce nearly two years after they initially announced their split in June 2015. The couple filed the documents together and sought joint legal and physical custody of their three kids.

Affleck and Garner finalized their divorce in October 2018 — three years after separating.

5. Lindsay Shookus

Affleck kept his relationship with the Saturday Night Live producer quiet until July 2017, but people later confirmed they started dating in 2014 while he was still married to Garner.

Someone close to Affleck and Garner said they were having a secret relationship, doing things like sending cute texts and meeting up.

It seemed like Affleck and Shookus were getting serious because they moved into a New York City apartment together in November 2017. However, they broke up in August 2018, and he briefly dated someone else named Shauna Sexton.

Affleck and Shookus got back together in February 2019 but ended things for good in April.

6. Shauna Sexton

After dating Shookus, Affleck was seen having dinner with Sexton at Nobu in Malibu on August 16, 2018, just a few days before he went to rehab for help with alcohol issues on August 22.

It was confirmed that Affleck and the Playboy model broke up after being together for two months. They decided to end things after going to Big Sky, Montana.

This happened shortly after they had a romantic vacation there, and Sexton, who is 22, shared a picture of Affleck, who is 46, on her social media for the first time.

7. Ana de Armas

Ben and Ana dated since March 2020, then later went on a vacation together in Cuba, Ana’s home country, and then later to Costa Rica for a weekend and romantic getaway before returning to LA.

During summer and quarantine, they were often seen together in Los Angeles. The actress from Knives Out confirmed they were a couple in April on Instagram, where she posted pictures of them celebrating her 32nd birthday.

In June, she went on a family vacation to Georgia with Affleck, his kids, and his mom, Christine. People said she got along well with the children. But now, after almost a year, Ben Affleck and Ana de Armas have decided to break up.

Who is Ben Affleck Dating Now?

On May 26, Us Weekly said that Jennifer Lopez and Ben Affleck are back together. A source said they are really happy with each other. Then, on Saturday, July 16, they got a marriage license in Clark County, NV, and officially got married. Someone close to them confirmed this.

Afterward, they went to Paris with some of their kids for a honeymoon and J.Lo’s work trip. They had lunch, took a two-hour private tour of the Seine, and visited the Picasso Museum. They dressed up for dinner at night, held hands, and laughed together.

In September 2022, Lopez put up some pictures from her wedding in her JLo newsletter. She also talked about what happened during the ceremony, the party after, and the next day’s brunch.

She mentioned that during the wedding speech, Affleck said something sweet, such as, “This is like heaven. Right here. We’re in it now.”

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