Ben Affleck's Dating History

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Ben Affleck has been a Hollywood staple for decades, with many loving his versatile projects and getting any and every detail they can about his A-list-packed love life.

Speaking of his love life, Affleck has been in the news cycle for so long because of his flings, girlfriends, and wives.

Did you know that before he started dating Hollywood actresses, he was actually in a seven-year relationship with his high school sweetheart? Do you remember his short-lived flings in between his marriages?

We all know about his marriages with Jennifer Lopez, Jennifer Garner, and his relationship with Gwyneth Paltrow, but there’s so much more to his dating history than you may realize.

Below check out Affleck’s full dating history:

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Jennifer Lopez (Again!) (2021-)

Jennifer Lopez (Again!) (2021-)
Jennifer Lopez (Again!) (2021-)

In 2021, Jennifer Lopez and Affleck rekindled their romance, and truly shocked the world. They got engaged a year later, and married in a lavish ceremony. Since then, they’ve been going to multiple A-list events and PDA-ing it up.

Ana de Armas (2019-2021)

Ana de Armas (2019-2021)
Ana de Armas (2019-2021)

While shooting the film Deep Water in 2019, Ben Affleck and Ana de Armas fell in love. They were inseparable for years, and were often seen vacationing and spending time together, even throughout the COVID-19 quarantine.

However, by Jan 2021, sources told People that “She broke it off…Their relationship was complicated.”

Katie Cherry (2019)

Katie Cherry (2019)
Katie Cherry (2019)

Affleck had another brief fling, in 2019 with musician Katie Cherry. They reportedly met on Raya, and dated for a few months in 2019.

Shauna Sexton (2018)

Shauna Sexton (2018)
Shauna Sexton (2018)

And soon after Affleck split from Shookus, he had a brief fling with model Shauna Sexton, from Aug 2018 to Oct 2018.

Lindsay Shookus (2017-2019)

Lindsay Shookus (2017-2019)
Lindsay Shookus (2017-2019)

Okay, so a few months after Affleck and Jennifer Garner filed for divorce, he was seen with Lindsay Shookus. So there’s a lot of hearsay on how they got together, with some saying it happened by chance and others saying they both had affairs with their partners before getting together.

They were hot and heavy from 2017 to 2018, but got back together for aa couple months in 2019.

Jennifer Garner (2004-2018)

Jennifer Garner (2004-2018)
Jennifer Garner (2004-2018)

Jennifer Garner and Affleck’s relationship began in 2004 when they met on the set of the movie Daredevil. Within a year, they got engaged, and by June 2015, they were married. They welcomed three children together named Violet, born Dec 2005, Fin, born Jan 2009, and Samuel, born in Feb 2012.

However, in June 2015, after 10 years of marriage exactly, they announced they were divorcing and by Oct 2018, it was finalized.

Enza Sambataro (2004)

Enza Sambataro (2004)
Enza Sambataro (2004)

Soon after splitting from Lopez, Affleck had a brief fling with exec Enza Sambataro, in 2004.

Jennifer Lopez (2002-2004)

Jennifer Lopez (2002-2004)
Jennifer Lopez (2002-2004)

Jennifer Lopez and Affleck fell in love on the set of the film Gigli, and by 2002, they fell in love. They appeared in a couple more projects together, and got engaged by the end of 2002, per People. In 2003, they postponed their wedding and then broke up days before, due to the paparazzi and pressure they faced.

Gwyneth Paltrow (1997-2000)

Gwyneth Paltrow (1997-2000)
Gwyneth Paltrow (1997-2000)

Per Wonderwall, Affleck and Gwyneth Paltrow met through Harvey Weinstein at Miramax’s pre-Academy Awards party in 1997. They hit it off immediately, and had an on-again, off-again relationship from 1997 to 2000. They starred in two films together, and they called it quits in Nov 2000, ahead of the premiere of their film Bounce.

Cheyenne Rothman (1990-1997)

Cheyenne Rothman (1990-1997)
Cheyenne Rothman (1990-1997)

Cheyenne Rothman was Ben Affleck’s high school sweetheart. They met at summer camp, and were together for seven years, from 1990 to 1997. Not much is known about their romance, or how they broke up.