When Ben Affleck first popped up in photos with a blonde woman who wasn’t Jennifer Garner back in the summer of 2017, the internet basically had a collective "wait, who?" moment. That woman was Lindsay Shookus. She wasn't an actress or a model. She was a powerhouse producer at Saturday Night Live, the kind of person who decides which celebrities are cool enough to host the show.
Their relationship was a whirlwind that didn’t fit the typical Hollywood script. It wasn’t just about red carpets; it was about recovery, long-distance struggles, and a very messy timeline that still gets debated in the comments sections of gossip blogs today.
The Timeline That Raised Every Eyebrow in Hollywood
If you ask the official reps, Ben Affleck and Lindsay Shookus started dating in 2017, shortly after he and Jennifer Garner filed for divorce. But if you listen to the whispers from the SNL hallways and various "insiders" quoted by People, the story goes back much further.
There are persistent reports that the two actually met when Ben hosted SNL back in 2013. At that time, Ben was still married to Garner, and Lindsay was married to Kevin Miller, a fellow SNL producer. Some sources claim they "full-on had an affair" for years, meeting up at the Mandarin Oriental in New York while Ben was in town for press.
Jen Garner allegedly found out in 2015. Rumor has it she even confronted Lindsay in person during a work trip to NYC, telling her to stay away from her husband. Whether the romance started in 2013 or 2017, by the time they went public at a dinner in Los Angeles in July 2017, the drama was already baked in.
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Why Lindsay Shookus Was "The One That Got Away"
Honestly, Lindsay seemed like exactly what Ben needed. She wasn't looking for fame; she already had a massive career behind the scenes. She has four Emmys. She’s the woman who booked Miley Cyrus and Adele for SNL. She understood the industry but didn't need the spotlight.
Friends of the couple often said she was "catnip" to him because she was smart, opinionated, and grounded. She lived a real life in New York with her daughter. During their peak, she was seen supporting his sobriety, attending meetings with him, and even getting him into meditation. It looked like he’d finally found a partner who could handle the "Hollywood" of it all without being consumed by it.
The Breakdown: New York vs. Los Angeles
The biggest enemy of this relationship wasn't another person. It was the flight time between JFK and LAX.
- Ben’s Base: He had to be in Los Angeles to co-parent his three kids with Jennifer Garner.
- Lindsay’s Career: She was the head of the talent department at SNL in New York. You can't produce a live show from 3,000 miles away.
- The Struggle: They tried the "bicoastal" thing for over a year, but distance creates gaps that are hard to fill when life gets messy.
The Heartbreaking Reason for the 2018 Split
In August 2018, things fell apart. While some reports blamed the distance, the truth was much darker. Ben was spiraling. His struggle with alcohol addiction reached a breaking point, and Lindsay reportedly felt helpless.
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A source told People at the time that Lindsay "had to let him hit bottom." She had been his support system, but she realized she couldn't fix him. It was a classic case of loving someone but needing to step away for your own sanity. Just days after they split, Jen Garner was the one who famously drove Ben to rehab after staging an intervention.
The Short-Lived 2019 Reunion
They actually tried again. In early 2019, Ben and Lindsay were spotted grabbing coffee and dinner in New York and LA. He looked healthier; she looked happy. They even walked the red carpet together for his movie Triple Frontier.
But the same old problems hadn't gone away. By April 2019, it was over for good. There was no big scandal this time—just two people in different phases of life. Ben was focused on his sobriety and his kids, and Lindsay was rooted in her New York life. It was a quiet end to a relationship that had started with a roar of tabloid headlines.
Where They Are Now
Ben, as everyone knows, eventually found his way back to Jennifer Lopez (and then faced a whole new set of public trials). Lindsay Shookus stayed at SNL until 2022, ending a legendary 20-year run at the show. She’s now a co-founder of "Women Work F#cking Hard," a networking community for female entrepreneurs.
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The legacy of their relationship is a reminder that even the "perfect" match on paper can't always survive the reality of addiction and geography.
What We Can Learn from the Ben and Lindsay Era
- Support has limits: You can't keep someone sober if they aren't ready to be. Lindsay’s decision to leave was a lesson in setting boundaries.
- Timing is everything: Being "the right person at the wrong time" is a real thing, especially when kids and careers are anchored in different time zones.
- Privacy is possible: Despite Ben's massive fame, they managed to keep the intimate details of their daily life relatively quiet compared to his other high-profile romances.
If you’re following the lives of these two today, focus on their professional pivots. Ben is leaning back into directing and production with his company Artists Equity, while Lindsay is redefining leadership for women in business. Sometimes the end of a relationship is just the necessary fuel for a new chapter in a career.
Check out Lindsay's new venture if you’re interested in how she’s translated her SNL talent-spotting skills into the entrepreneurial world. It's a far more interesting story than the old paparazzi photos from 2017.