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If you’ve ever listened to his podcast Life is Short, you already know Justin Long is basically the human equivalent of a warm hug. He’s self-deprecating, he’s funny, and he seems to have this weirdly magical ability to stay best friends with every single person he’s ever dated.
Honestly, it’s a little intimidating.
Most people know him as the "Mac guy" or that dude from Dodgeball, but in the world of celebrity gossip, Justin Long dating history is legendary. He doesn’t just date; he falls in love. Hard. We’re talking about a guy who has been linked to some of the most talented women in the industry, from Drew Barrymore to Amanda Seyfried, before finally settling into a whirlwind marriage that has everyone (including his exes) cheering him on.
But it wasn't always a straight line to the "happy ever after" we see today.
The Drew Barrymore Era: A Lesson in Post-Breakup Grace
Let’s go back to 2007. This was the peak of the rom-com era. Justin and Drew Barrymore met on the set of He’s Just Not That Into You, and for the next few years, they were the "It" couple for anyone who liked their celebrities a little quirky and grounded.
They were on, they were off. Then they were on again.
They even starred in Going the Distance while they were together (or maybe they had just broken up? It was hard to keep track). But here’s the thing that makes Justin different: when they finally called it quits for good in 2010, there was no drama. No shady tweets. No "sources" leaking stories about messy closets.
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Fast forward to 2022, and Justin is appearing on The Drew Barrymore Show. They’re crying. They’re hugging. Drew literally called him one of her favorite people. It’s rare to see that kind of genuine affection between exes in Hollywood. It set a tone for how Justin handles his personal life—with a lot of maturity and very little ego.
The Surprise Connection with Amanda Seyfried
After Drew, things were a bit quieter until 2013. That’s when he started dating Amanda Seyfried.
How did they meet? Instagram.
This was back when sliding into DMs wasn’t even a phrase yet. Amanda saw a funny post Justin made about a snail and reached out. They dated for about two years, and for a while, it looked like they were the real deal. They lived together, they shared a dog (the famous Finn), and they seemed perfectly matched in their weirdness.
They split in 2015. Reports at the time said it was the classic "hectic schedules" excuse, which is usually code for "we grew apart but don't want to talk about it." But even then, there was zero bad blood.
A Quick Look at the Timeline:
- Kaitlin Doubleday (2005-2007): Long before the massive fame, he dated his Accepted co-star.
- Maggie Q (2007): A short-lived romance that most people forget about.
- Kirsten Dunst (2008): There were rumors, but honestly, it was never really "official."
- Lauren Mayberry (2016-2018): He was linked to the lead singer of CHVRCHES for a couple of years, though they kept things incredibly private.
Meeting the One: The Kate Bosworth Whirlwind
If you had told someone in 2020 that Justin Long and Kate Bosworth would be married with a child by 2026, they probably would have laughed. They seemed like they lived in two different worlds.
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But then came 2021.
They met while filming a movie in Arkansas. It wasn't an immediate tabloid explosion. Instead, it was a slow burn. Justin started dropping hints on his podcast about a "new girlfriend" who liked pineapple on her pizza.
Then came the Ireland photos. Then the PDA in Hawaii.
By April 2023, they confirmed they were engaged. But Justin, being Justin, couldn't wait. He started calling her his "now-wife" on his podcast before they even had a ceremony. It turned out they had a super casual, impromptu wedding at the Rockaway Hotel in Queens. No massive guest list. No $2 million dress. Just two people who were tired of waiting.
Why 2025 and 2026 Changed Everything
The most recent chapter in Justin Long dating history is arguably the most significant. In July 2025, Justin and Kate welcomed their first child, a daughter, via surrogacy.
It changed the dynamic of their public personas. They went from the "cool indie couple" to the "relatable parents." Recently, in early 2026, they’ve been very vocal about "aging naturally" together. They’re doing the whole "we love each other's wrinkles" thing, which is refreshing in an industry obsessed with Botox.
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They seem solid.
You can tell by the way he talks about her—she’s not just a partner; she’s his best friend. They even survived the "lost wedding ring" incident of 2023, which Justin admitted to on national TV with his usual "oops" charm.
What can we learn from all this?
Honestly, Justin’s history proves that you don't have to be a "bad boy" to win in Hollywood. He’s consistently dated some of the most impressive women in the world by just being... a nice guy.
If you're looking for a blueprint on how to handle your own past relationships, look at him. He doesn't delete the photos. He doesn't talk trash. He just moves forward with a lot of respect for the people who used to be in his life.
Next Steps for You:
If you want to see the chemistry for yourself, go back and watch House of Darkness. It’s the movie where they actually fell in love. It’s a horror-thriller, which is a weird place to find romance, but hey, it worked for them. You should also check out the 2022 episode of The Drew Barrymore Show featuring Justin—it’s a masterclass in how to be a "good ex."