Ben Affleck definitely has a pattern when it comes to his love life. He falls hard for famous actresses and their romances become so high profile due to the nature of two A-listers coming together.
But sadly his personal demons have also got in the way of his relationships throughout the years. As the 48-year-old is coming up on his one year dating anniversary with 32-year-old Cuban-Spanish actress Ana de Armas, we’ve got a look back on all of the women Ben Affleck has loved.
Ben Affleck and his bestie Matt Damon became young Hollywood royalty when the then-27-year-olds won an Oscar for Best Original Screenplay in 1998 for Good Will Hunting. It also landed Ben a gorgeous girlfriend in actress Gwyneth Paltrow, 48.
Ben Affleck and Gwyneth Paltrow co-starred in 1998’s Shakespeare in Love while very much in love themselves. Sadly, they had broken up by the time she won the Oscar for Best Actress for the film in 1999.The pair rekindled their romance as they starred in the 2000 drama Bounce, but ended things for good in late 2000.
“Bennifer” became a thing during the 2002 filming of their disastrous movie bomb Gigli, while Jennifer Lopez was still married to backup dancer Cris Judd. But she and Ben Affleck could not fight their passion and fell madly in love. She divorced Cris Judd, and Jennifer Lopez and Ben Affleck got engaged in late 2002. He presented her with a 6.1 carat pink diamond ring worth $2.5 million.
The couple became victims of overexposure, and their relationship drama came to a head when the pair called off their September 2003 wedding just a few days before it was supposed to go down. While they ended up staying together, their nuptials never happened and they called off their engagement and split for good in late Jan. 2004.
Ben Affleck didn’t stay single for long after their breakup. He admitted in a 2017 Playboy interview that he fell in love with actress Jennifer Garner, while they were filming the 2003 film Daredevil…while he was still in a relationship with Jennifer Lopez! Though he didn’t act on his feelings until they had split.
Ben Affleck and Jennifer Garner made their relationship public on Oct. 23, 2004, kissing and cuddling in the stands at a Boston Red Sox game. He proposed to her on April, 17, 2005, her 33rd birthday. They wed two months later on June 29, 2005 in a four person ceremony on the beach in the Turks and Caicos.
After having three children together, Ben Affleck raised eyebrows when he left a family vacation in the Bahamas to fly to a charity poker tournament in Las Vegas on June 26, 2015 with the family’s nanny Christine Ouzounian, and got divorced after he cheated on her.
Ben Affleck stepped out with Saturday Night Live producer Lindsay Shookus in April 2017, even though he was still legally married to Jennifer Garner. They were open about their dating as she accompanied him on a trip to London in early July 2017, and once they returned to L.A. were regularly photographed holding hands on outings and looking very much in love.
But Ben Affleck was caught in the company of former Playboy model Shauna Sexton, taking her to dinner at Nobu Malibu on August 16, 2018, and she was photographed over the next few days coming and going from his house.
Ben Affleck was snapped with former Playboy model Shauna Sexton grabbing fast foot at a Jack in the Box on Aug. 19, 2018. Four days earlier, they had dinner at Nobu Malibu, even though he and Lindsay Shookus hadn’t officially split yet. Apparently Ben Affleck had fallen off the wagon and was partying hard with Shauna Sexton, who was photographed arriving at his house with several bottles of alcohol.
Ana de Armas
Ben Affleck and Ana de Armas met in 2019 while filming the thriller Deep Water, and began a relationship after shooting wrapped. They were first spotted out as a couple, visiting Havana, Cuba together in early March 2020. The couple spent quarantine together at his house. They are still together and looking happier than ever.
Source: Hollywood Life