Actor Ben Affleck
Source: Getty Images

Ben Affleck Has Dated Some of Hollywood's Elite Actresses and Singers

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May. 11 2021, Published 1:59 p.m. ET

Navigating the world of Hollywood relationships is easier said than done. Many celebrities tend to play the breakup-to-make-up game, while others simply try their best to leave us guessing. One celebrity who does a little bit of both is none other than actor Ben Affleck.

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Over the years, we’ve seen Ben dip in and out of plenty of high-profile relationships. From Gwyneth Paltrow to Jennifer Garner, the playboy has made his rounds in the industry. However, fans might not know about some of the other women Ben has dated. Read on to get the lowdown on Ben’s relationship history.

Ben Affleck’s first high-profile relationship was with Gwyneth Paltrow.

Ben Affleck and Gwyneth Paltrow
Source: Getty Images

Before Ben transformed into a Hollywood playboy, he was truly smitten with actress Gwyneth Paltrow. According to the Evening Standard, Ben and Gwyneth started dating in 1997 after the Emma star split from Brad Pitt.

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Gwyneth and Ben reportedly met at a dinner party held by Harvey Weinstein, and the rest was history.

Ben and Gwyneth dated for two years, from 1997 to 1999. They even starred on screen together in the 2000 film Bounce, where they rekindled their relationship briefly but later split for good. 

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Ben and Jennifer started their love story in 2002.

J.Lo and Ben Affleck
Source: Getty Images

One of Ben's most memorable relationships is the one he had with Jennifer Lopez. Fresh off her divorce from Cris Judd, J.Lo began to date Ben after they filmed the movie Gigli together. And in November 2002, the pair took the next step to get engaged.

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Throughout their time together, they became a fan-favorite couple. Dubbed "Bennifer," the duo were Hollywood relationship goals over the next few years. However, the pair decided to break off their engagement in January 2004. 

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Nearly 20 years later, it seems like the couple has decided to give their relationship another go. After ending her engagement to Alex Rodriguez, Jennifer has been spotted hanging out with Ben again.

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Ben married actress Jennifer Garner after working together on 'Pearl Harbor' and 'Daredevil.'

Jennifer Garner and Ben Affleck
Source: Getty Images

True to his nature, Ben found love on the film set once again after working with Jennifer Garner on Pearl Harbor and Daredevil. The couple made their relationship official in October 2004, just nine months after he severed ties with J.Lo.

Evening Standard reports that the two got engaged at Jennifer's 33rd birthday. They later married in 2005. During the course of their marriage, they had three children: Violet, Seraphina, and Samuel.

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After spending 10 years together, the couple separated in 2015 and finalized their divorce in 2017. Rumors of infidelity were said to be their demise.

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Ben and 'Playboy' model Shauna Sexton were also an item.

Former Playboy model Shauna Sexton
Source: Instagram

Ben is known to snag some of the hottest women in the industry. So, his relationship with former Playboy model Shauna Sexton made perfect sense. According to Us Weekly, Ben and Shauna ended their short-lived fling in August 2018.

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The outlet reported that the duo only spent two months together, which is a far cry from Ben's past relationships. Things came to a screeching halt after the duo vacationed in Montana together. 

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Ben later moved on to fellow co-star Ana De Armas in 2020.

Actress Ana De Armas
Source: Instagram

Ben wastes no time moving on from his relationships. And after meeting actress Ana De Armas on the set of Deep Water, the two sparked couple rumors in March 2020. 

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According to Us Weekly, the pair made their romance public in May 2020. Per a source, the couple were "very serious" and Ben had intentions of introducing his three children to the star. However, things took a turn and the couple later broke up in January 2021.

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