He’s Got Game! See Ben Affleck’s Dating History From Jennifer Garner to Jennifer Lopez

Cheyenne Rothman

Seems like Ben was a ladies man from the start. Cheyenne Rothman was quite possibly Ben’s first love. The two met as teens at summer camp and were high school sweethearts. They dated on-and-off for over seven years before officially going their separate ways in 1997.

Gwyneth Paltrow

The actor and Gwyneth Paltrow first linked up in 1997 after meeting at a dinner party. They worked alongside each other in the 1998 film Shakespeare in Love but ended things in 1999. They joined each other on-screen once again for the movie Bounce and rekindled their romance on set. Unfortunately, they broke up for good in 2000.

Jennifer Lopez (The 1st Time)

Jennifer Lopez and the handsome hunk met while filming their movie Gigli. The couple got engaged in November 2002, shortly after Jen finalized her divorce from Cris Judd in June of that year. Although they made quite the couple, they ended their engagement in January 2004.

Jennifer Garner

The handsome stud’s relationship with Garner was one of his longest. Although Ben and Jen costarred in Pearl Harbor in 2001 and in Daredevil in 2003, their relationship status wasn’t confirmed until October 2004. Ben later proposed in April 2005 and the duo said “I do” in June 2005.

After welcoming three kids — Violet, Seraphina and Samuel — and a decade of marriage, the couple separated in June 2015 and finalized their divorce in October 2018.

In February 2020, Ben admitted his “biggest regret” was splitting from the mother of his children in an interview with The New York Times.

Although they are no longer an item, the A-listers are model coparents. “While Ben and Jen both have busy schedules, they always put their [kids] — Violet, Seraphina and Samuel first,” an insider told In Touch exclusively. “They’ve chosen not to employ a team of nannies and work together to ensure their children have the most hands-on, stable, loving upbringing possible.”

Lindsay Shookus

The Argo actor and Lindsay Shookus went public with their relationship in July 2017.  After only a few months of dating, they moved in together in November of that year. Although their relationship moved fast, they split in August 2018, before reconciling in February 2019. Things between the two ended for good in April of that year.

Shauna Sexton

While Ben was on a break from the Saturday Night Live producer, he was spotted with Playboy model Shauna Sexton in August 2018. They briefly dated for two months.

Katie Cherry

The actor and Katie Cherry briefly dated after meeting on the dating app Raya in October 2019. “It’s nothing serious at this time,” an insider exclusively told In Touch in November.

Ana de Armas

After meeting on the set of their movie, Deep Water, he and Ana sparked dating rumors in March 2020.

“They’re playing a couple on the film, a husband and wife with some very dark secrets, and their chemistry is off the charts. They’ve become very close,” a source exclusively told In Touch that month, adding that Ben has “really fallen for her.” “Ben loves that she’s originally from Cuba, he can’t get enough of her culture, and he loves her accent.”

Ben and Ana were spotted on many outings throughout 2020, even taking a romantic vacation to Cuba together. The actor’s kiddos often accompanied the two as they made trips to the grocery store amid the coronavirus pandemic.

Just as things seemed to be going well, though, a separate source revealed the “dynamic [of their relationship] changed” when Ben and Ana “moved in together.”

In January 2021, another source confirmed the couple called it quits after nearly one year of dating. “Ana ended the relationship,” the insider exclusively divulged. “Ana still cares for Ben, but she can’t see a future with him. It wasn’t working and they weren’t on the same page.” While the former flames are “on amicable terms and still talk,” their relationship “is over.”

Jennifer Lopez (Round 2)

Seventeen years after their 2004 split, Ben and J. Lo reignited romance rumors when he was spotted visiting her mansion in Los Angeles in April 2021.

On April 8, 2022, Jen announced her second engagement to Ben nearly one year after they got back together. The pair tied the knot three months later in July 2022 in Las Vegas, followed by a wedding at his Georgia estate one month later.

In her February 2024 documentary about their romance, The Greatest Love Story Never Told, Jennifer revealed why she and Ben called off their 2003 wedding. “We had a big wedding planned — 14 ushers and bridesmaids — and three days before, we just crumbled under the pressure,” she said. Ben agreed, adding that they broke up because of the “massive amount of scrutiny around our private life.”

By April 2024, the couple was crumbling once again. After reports of trouble in their marriage and the two seemingly spending time apart, a source exclusively told In Touch on May 15, 2024, that Ben had “moved out” of their shared home and he and J. Lo were on the outs.

“The writing is on the wall – it’s over,” the insider said. “They’re headed for a divorce — and for once, [Ben’s] not to blame!”

On August 20, 2024 – the two-year anniversary of their Georgia wedding – Jen filed for divorce from Ben and listed the date of separation as April 26, 2024. The official divorce filing came after the pair spent a lot of time apart throughout the summer.