7 Surprising Truths About Justin Long And Drew Barrymore's Enduring Love And Mature Friendship

The relationship between Justin Long and Drew Barrymore remains one of Hollywood’s most fascinating and surprisingly mature post-breakup dynamics. Despite their highly publicized on-again, off-again romance that spanned from 2007 to 2010, the former couple has transformed their connection into a deep, enduring friendship that continues to make headlines, especially as of late 2024 and early 2025. Their story is a powerful testament to the possibility of moving past romance while maintaining a profound love and respect for one another, a narrative that has been openly discussed in recent interviews and emotional television reunions.

This mature dynamic is particularly noteworthy now that Justin Long is happily married to actress Kate Bosworth, and Drew Barrymore is navigating her own single life with a fresh outlook on dating in 2024. Their ability to celebrate each other's happiness and reflect on their past with such genuine affection offers a rare and inspiring glimpse behind the celebrity curtain, proving that some Hollywood romances never truly end, they just evolve.

Justin Long and Drew Barrymore: A Biographical Snapshot

To fully appreciate their enduring connection, it's essential to understand the careers and personal lives they have built both together and apart.

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Justin Long's Profile

• Full Name: Justin Jacob Long
• Date of Birth: June 2, 1978 (Age 47 as of late 2025)
• Place of Birth: Fairfield, Connecticut, U.S.
• Career Highlights: Known for roles in Galaxy Quest, Jeepers Creepers, DodgeBall: A True Underdog Story, the "Mac" in the "Get a Mac" Apple commercials, and the horror film Barbarian.
• Past Relationships: Dated Drew Barrymore, Amanda Seyfried.
• Current Relationship Status: Married to Kate Bosworth (since May 2023).

Drew Barrymore's Profile

• Full Name: Drew Blyth Barrymore
• Date of Birth: February 22, 1975 (Age 50 as of early 2025)
• Place of Birth: Culver City, California, U.S.
• Career Highlights: Rose to fame as a child star in E.T. the Extra-Terrestrial; known for films like The Wedding Singer, Charlie's Angels, and 50 First Dates. She is currently the host of the daytime talk show, The Drew Barrymore Show.
• Past Marriages: Jeremy Thomas (1994), Tom Green (2001–2002), Will Kopelman (2012–2016).
• Children: Two daughters, Olive and Frankie, with ex-husband Will Kopelman.
• Current Relationship Status: Single (as of late 2024).

The Emotional Reunion That Shocked Fans

One of the most significant and most-talked-about moments in their shared history since their breakup was Justin Long’s appearance on The Drew Barrymore Show. This emotional reunion, which took place in 2022 during the show's season 3 premiere, was the first time the two had seen each other in a long while and provided the public with a clear view of their current dynamic.

1. They Cried on Camera: The reunion was far from a standard, professional interview. As they embraced, both stars—known for their bubbly personalities—broke down in tears, a raw display of the deep bond they still share. They reminisced about their time together, with Barrymore tearfully expressing, "I love that we maintained our love because I know for me, I'll love you always."

2. Reflecting on a 'Hedonistic' Romance: During the chat, they openly discussed the intensity of their romantic relationship, which Barrymore described as "hedonistic" and "fun." This candid reflection highlighted the passionate nature of their connection while they were dating, which included starring together in the films He's Just Not That Into You (2009) and the romantic comedy Going the Distance (2010).

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3. Acknowledging the Pain of the Breakup: The emotional intensity of the reunion stemmed from the difficulty of their breakup. Long mentioned that they had been through "a lot" together, and the tears confirmed that the split, which happened over a decade ago, was a significant and painful event for both of them, underscoring the depth of their affection.

The Mature Dynamic: Justin Long's Marriage and Drew's Approval

The truest measure of their mature friendship came with the news of Justin Long’s marriage to actress Kate Bosworth. The way Drew Barrymore handled this significant life change for her ex-boyfriend cemented their status as one of Hollywood's most evolved former couples.

4. Drew Applauded His Engagement: When Kate Bosworth appeared on The Drew Barrymore Show, Barrymore didn't shy away from the topic. Instead, she publicly and enthusiastically applauded the couple’s engagement, expressing her happiness for them both. This act of genuine support for her ex-partner's new chapter is a powerful example of an "enduring affection" that transcends romantic jealousy.

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5. Justin's 'Deep Affection' Endures: Justin Long has consistently spoken about his feelings for Drew in a way that is respectful to his current wife, Kate Bosworth, while still honoring his past. In a recent appearance on Jesse Tyler Ferguson’s podcast, Dinner's on Me, Long reflected on his "enduring love" and "deep affection" for Barrymore, clarifying that his love for her now is simply "in a different way" than when they were dating. He stated he will "always root for" her.

6. A Model for Post-Breakup Friendships: Their dynamic has become a quiet model for how celebrity exes can maintain a healthy, supportive friendship. They have shown that it is possible to cherish the memories of a passionate romance while fully embracing new, separate futures. This is a key reason why their story continues to resonate with fans and the media, proving that a breakup doesn't have to mean a complete erasure of the love that was once shared.

Drew Barrymore's New Chapter and Dating Outlook in 2024

As Justin Long enjoys his married life with Kate Bosworth, Drew Barrymore has been open about her own journey as a single mother and her evolving approach to dating in 2024.

7. A New Outlook on Love: As of late 2024, Drew is single but has expressed a new, more measured outlook on her love life. After her divorce from Will Kopelman in 2016, the actress has prioritized her daughters and her career, but she has recently spoken about being ready to approach dating again with a fresh perspective. Her public statements show a woman who has learned from her past, including her relationship with Long, and is moving forward with clarity and self-awareness.

The narrative of Justin Long and Drew Barrymore is not a story of a couple who "got back together," but a far more interesting tale of two people who grew up, found happiness separately, and managed to preserve the profound emotional connection that first brought them together. Their mutual respect and open communication serve as a refreshing blueprint for modern relationships.