Ben Affleck’s Full Dating History in Chronological Order

And then he popped the question with a 6.1-carat pink solitaire.

But things went south pretty fast, and they called off their wedding just days before it was scheduled in September 2003:

“Due to the excessive media attention surrounding our wedding, we have decided to postpone the date. When we found ourselves seriously contemplating hiring three separate ‘decoy brides’ at three different locations, we realized that something was awry. We began to feel that the spirit of what should have been the happiest day of our lives could be compromised. We felt what should have been a joyful and sacred day could be spoiled for us, our families, and our friends.”

Cut to January, and Jen’s rep dropped a statement saying “I am confirming the report that Jennifer Lopez has ended her engagement to Ben Affleck. At this difficult time, we ask that you respect her privacy.”

2004 t0 2015: Jennifer Garner

Ben and Jennifer Garner connected on set of Daredevil in 2002, but didn’t start dating until 2004—after he ended his engagement to Jennifer Lopez. Ben proposed in April 2005, they got married in June 2005, and went on to have three kids: Violet, Seraphina, and Samuel. Cut to 2015 and theories started to swirl about Ben cheating with the couple’s nanny, which his rep called “complete garbage and full of lies.” Regardless, the couple announced their split in June, saying “After much thought and careful consideration, we have made the difficult decision to divorce. We go forward with love and friendship for one another and a commitment to co-parenting our children whose privacy we ask to be respected during this difficult time. This will be our only comment on this private, family matter. Thank you for understanding.”

Jen opened up about the nanny rumors the following year to Vanity Fair, saying “We had been separated for months before I ever heard about the nanny. She had nothing to do with our decision to divorce. She was not a part of the equation. Bad judgment? Yes. It’s not great for your kids for [a nanny] to disappear from their lives. It was a real marriage. It wasn’t for the cameras. And it was a huge priority for me to stay in it. And that did not work.”

The couple officially divorced in 2018, but continued to be close friends and coparents.

July 2017 to August 2018: Lindsay Shookus

Ben started dating SNL’s Lindsay Shookus, but the relationship didn’t last long and they split up in August of 2018. A source tells People he was “never fully committed” to her.

August 2018: Shauna Sexton

Ben was spotted with Playboy model Shauna Sexton and they dated for a couple months before parting ways. A friend of Ben’s told People, “There was nothing to split from as it has been casual. He enjoyed being with her but is working on himself, and being together with her at this time is not something that works. He will date in the future, but for now his focus is on his sobriety, family and his next project.”

November-ish 2019 to January 2021: Ana de Armas

Ben and Ana met on set of Deep Water in November 2019, and by March a source told People they were “definitely dating.” Ana briefly moved in with Ben, but the relationship wasn’t mean to last and they split…over the phone. Ben even (seemingly/iconically/infamously) threw out his Ana de Armas life-sized cut-out.

Per a Page Six insider, “[Ben] would not commit to having more kids. She is in her 30s. It was a deal breaker.”

May 2021 to May 2024: Jennifer Lopez

Bennifer (J.Lo and Ben) are back on! TMZ reported that their rekindled relationship had been “been building since February” when Ben “started flooding her with emails” full of “loving and longing.” They got engaged in 2022 with a giant green ring (Ben has…really specific taste):

And then got married in August:

Cut to May 2024 and breakup rumors kicked off thanks to J.Lo attending the Met Gala solo. The couple spent summer apart, Ben moved out of their shared home, and J.Lo filed for divorce on August 20 (the two-year anniversary of her and Ben’s Georgia wedding).

A source told Page Six that “He has humiliated her. He was the one who initiated getting back together. He’s humiliated her because she made a big deal that he’s the love of her life. They just had two weddings two years ago. This is some kind of a record—they’re not young kids.”

August 2024: Kick Kennedy

Everyone was minding their own business and then Page Six came out with a report that Ben was “hanging out with” RFK Jr’s daughter Kick Kennedy. Direct quote: “A Hollywood insider tells Page Six they have been spotted at the Polo Lounge at the Beverly Hills Hotel and other hot spots. The nature of their relationship remains unclear.”

Meanwhile a source told People they’ve been “spending time together,” while Ben’s rep pushed back with “There is no truth to any of it. I don’t know if they even know each other.”

Circa Right Now: No One (But Also He’s Into Jennifer Garner Again?)

A source told People in February that Ben had been “casually dating,” but that romance didn’t “seem to be a focus.” Meanwhile, he and Jennifer Garner were seen having a super flirty moment at their son’s paintball game, and a source told Page Six that Ben “would love another chance” with her and “would definitely be open to giving things another shot with Jen if the timing is ever right. At the same time, Ben knows it’s just not realistic at this time in their lives.”

That said, Ben “just got out of a marriage and finalized his divorce he is really busy with work and is focused on this new chapter. Plus, Ben respects Jen’s relationship with John [Miller] and would never come between them.”

More to the point, “The feeling is not mutual on Jen’s side. She’s happy with John and that’s just not where her head is at. She has a great co-parenting relationship with Ben, and that’s where things stand on her end at the moment.”

Annnnd that’s all! Guess we’ll…see what’s next.