Ben Affleck’s love life has been a hot topic since his career began in the ’80s.
The movie star has dated some of the most beautiful women in Hollywood, so here’s a look back at his former loves — from his high school sweetheart to his marriage to Jennifer Lopez and all the women in between.
Cheyenne Rothman
Ben Affleck and Cheyenne Rothman met while the “Justice League” star was still in high school.
He attended Cambridge Rindge and Latin High School in Cambridge, Mass., and the pair were high school sweethearts. Rothman went on to become a film director.
Gwyneth Paltrow
Affleck and Gwyneth Paltrow began dating after his split from Rothman in 1997. They starred in both “Bounce” and “Shakespeare in Love” together and their relationship lasted — off and on — for three years.
The Goop founder told Howard Stern in 2015 of her romance with Affleck, “I think [my parents] appreciated how he’s super intelligent and he’s really, really talented and so funny, but he was not in a good place in his life to have a girlfriend. I think they were OK with the two of us not being together.”
Jennifer Lopez
One of Affleck’s most high-profile relationships was his romance with Jennifer Lopez — which sparked the name “Bennifer” for the duo. They met in 2002 after starring in “Gigli” together, and sparked a media frenzy after their engagement.
The pair were meant to get married in Santa Barbara in 2003, but postponed their nuptials due to the “excessive media attention” surrounding the wedding, according to People.
The couple broke things off (for good?) in January 2004, with J. Lo’s rep saying in a statement that the singer had “ended her engagement to Ben Affleck,” adding, “At this difficult time, we ask that you respect her privacy.”
Meanwhile Affleck’s rep said, “I am not going to confirm anything about his personal life. We don’t want to get dragged into quicksand. Everybody wants a war. It’s not happening from our side.”
Jennifer Garner
Falling for yet another co-star, Affleck met Jennifer Garner on the set of 2001’s “Pearl Harbor” and starred together in 2003’s “Daredevil.”
They got married in June 2005 and welcomed three children — Violet, Seraphina and Samuel — during their relationship.
In 2015, sources told Page Six — amid reports of Affleck’s gambling and alleged liaisons with other women — that the pair had drifted apart and had been in professional therapy for years. The split was announced a day after their 10th wedding anniversary.
They finalized their divorce in 2018, but remain on good terms.
Lindsay Shookus
In 2017, Affleck confirmed his relationship with “Saturday Night Live” producer Lindsay Shookus.
“She’s enjoying it,” a colleague of Shookus told The Post at the time. “She never wanted to be on camera, but she’s comfortable getting a lot of attention.”
Affleck and Shookus were off and on throughout their relationship, but they ended things for good in 2019 due to their “hectic schedules,” according to Entertainment Tonight.
Shauna Sexton
Affleck was rumored to have had a fling with veterinary tech and former Playboy model Shauna Sexton in 2018.
Sexton was 23 when the she started dating Affleck, who was more than two decades older than her, and their relationship only lasted a couple of months.
Ana de Armas
Affleck and Ana de Armas met on the set of “Deep Water” as they filmed on location in New Orleans. The pair were a paparazzi’s dream amid the pandemic, often being photographed going for strolls in their LA neighborhood together.
In January, sources told Page Six the pair called it quits because they were in “different places” in their lives. “He would not commit to having more kids,” said the insider. “She is in her 30s. It was a deal-breaker.”
Jennifer Lopez
“Bennifer” is back on. Fresh off his breakup with de Armas, Affleck reportedly started sending love letters to Lopez while she was on set of her new movie, “Shotgun Wedding.”
Although sources previously said the exes were “strictly friends,” the duo were spotted partying together in Montana, once again sparking romance rumors, in May 2021.
In July 2021, Lopez made their love Instagram-official by posting a PDA-filled photo of the pair in honor of her 52nd birthday.
They then made their red carpet debut at the Venice Film Festival that September.
Seven months later, J.Lo sparked engagement rumors when she was seen wearing a massive ring on her left hand. She then confirmed Affleck proposed with a ring adorned with a very rare green diamond.
The couple tied the knot in a low-key ceremony at a “little chapel” in Las Vegas in July 2022.
