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A Timeline Of Ben Affleck’s Many Relationships

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Nearly three decades of headlines, three engagements, one marriage, and a 2021 reunion nobody saw coming — Ben Affleck’s love life has been front-page news since the Clinton administration.

Ben Affleck built a career as an Oscar-winning writer, director, and leading man, but for long stretches of that career, his personal life generated just as much ink as his movies. From a late-’90s fling with a co-star to the tabloid supernova known as “Bennifer” to a pandemic-era romance with Ana de Armas, Affleck’s relationships have tracked almost perfectly with the eras of celebrity gossip journalism itself. And as of May 2021, he’s back in the headlines for the same reason he first made them.

• Affleck and Jennifer Lopez called off their engagement in January 2004 after postponing their September 2003 wedding just days before the ceremony, driven off by paparazzi intrusion.
• He married Jennifer Garner in a private Turks and Caicos ceremony in June 2005; the couple had three children — Violet, Seraphina, and Samuel — before separating in June 2015 and finalizing their divorce in late 2018.
• In May 2021, Affleck and Lopez rekindled their romance following her split from Alex Rodriguez, spending time together in Los Angeles and on trips to Montana and Miami.

Gwyneth Paltrow and the Start of the Spotlight

Affleck’s public dating life begins with Gwyneth Paltrow, his co-star in 1998’s Shakespeare in Love. The two dated on and off from roughly 1997 to 2000, a relationship that unfolded just as celebrity magazines and early tabloid TV were ramping up their appetite for star couples. It ended quietly by 2000, but it set the template for what was coming: a leading man whose relationships would routinely become their own news cycle.

Bennifer 1.0 and the Wedding That Never Happened

Affleck met Jennifer Lopez in early 2002 on the set of Gigli, and the pairing — quickly shortened to “Bennifer” by the press — became the first true 21st-century celebrity-couple media circus. After Lopez finalized her divorce from dancer Cris Judd, Affleck proposed in late 2002 with a 6.1-carat pink diamond that became a tabloid character in its own right.

The couple set a wedding date for September 2003, but called it off just days beforehand, citing overwhelming paparazzi intrusion. They tried to hold the relationship together for a few more months before formally ending the engagement in January 2004.

They postponed their September 2003 wedding days before the ceremony — then called off the engagement entirely by January 2004.

Jennifer Garner: Marriage, Three Kids, and a Public Split

Later in 2004, Affleck began dating Jennifer Garner, his co-star from both Pearl Harbor and Daredevil. The relationship moved fast by comparison to Bennifer’s implosion — the two married in a private ceremony in Turks and Caicos in June 2005 and went on to have three children together: Violet, Seraphina, and Samuel.

Their marriage lasted a decade, playing out under constant tabloid coverage of Affleck’s personal struggles. The couple announced their separation in June 2015, filed for divorce in 2017, and finalized it in late 2018, with both committing publicly to co-parenting their three kids amicably. Readers who followed similar long-married-couple splits in Hollywood may recognize the pattern from Megan Fox’s own relationship history, another case where a high-profile marriage unraveled under constant public scrutiny.

The Post-Divorce Years: Shookus, Sexton, and de Armas

Following the Garner split, Affleck entered an on-and-off relationship with Saturday Night Live producer Lindsay Shookus that ran from 2017 to 2019, alongside a brief, tabloid-heavy fling with model Shauna Sexton in late 2018. Not every post-divorce rebound sticks, and Affleck’s dating life in this stretch reflected that — a pattern not unlike what played out for other stars navigating life after long marriages, including Sandra Bullock’s relationship with Bryan Randall.

In late 2019, Affleck began dating actress Ana de Armas after the two met filming the thriller Deep Water. The pair quarantined together through much of 2020, one of the more visible celebrity relationships of the pandemic era, before splitting amicably in January 2021 over differing lifestyle priorities.

Bennifer, Again

By May 2021, Affleck was back at the center of a full-blown media frenzy — this time because he and Jennifer Lopez had rekindled their relationship following her split from Alex Rodriguez. The two were spotted spending time together in Los Angeles, vacationing in Montana, and on a getaway in Miami, nearly two decades after their first engagement collapsed under the same kind of scrutiny.

Whatever comes next for Affleck and Lopez, the optics alone guarantee it’ll be covered with the same intensity as their first run in 2002 and 2003 — only this time both of them have already lived through exactly how that story can end.