Drew Barrymores Relationship Journey From Childhood Engagements to Third Marriage

Drew Barrymore’s romantic history is as colorful and dynamic as her career in Hollywood. The beloved actress and talk show host has traversed a complex landscape of love, engagement, and heartbreak throughout her life, often in the public eye. Though she has faced challenges and setbacks, Barrymore’s resilience and ability to maintain friendships with former partners demonstrate her growth and strength.

Barrymore, who has been in the spotlight since childhood, has had a series of relationships that reflect both the whirlwind nature of fame and the pursuits of personal happiness. While her sexual orientation is bisexual, she has only married men thus far—a reflection of her unique path through love and companionship.

Let’s take an in-depth look at some of her most significant relationships, engagements that didn’t pan out, and the marriages that shaped the woman we see today.

Drew Barrymore first found herself engaged at a remarkably young age. At just 16, she became engaged to Leland Hayward III, a 25-year-old who was already familiar with the entertainment scene. The engagement did not last, but it marked the beginning of Barrymore’s tumultuous relationship journey.

Following this, Barrymore found herself in a relationship with Jamie Walters, a fellow actor. Their romance lasted from 1992 to 1993, during which time Walters proposed with a diamond ring. However, despite their plans for a spring wedding in 1993, the couple ultimately decided against it. Their relationship was marked by youthful passion, as they famously got tattoos bearing each other’s names, a testament to their deep connection at the time.

Barrymore’s first official marriage came a bit later, at the age of 19, to Jeremy Thomas, a 31-year-old bar owner. After a whirlwind romance lasting just six weeks, they impulsively tied the knot in a late-night ceremony. However, the marriage was short-lived, ending in separation just 19 days later. Barrymore later described Thomas as someone who had married her for her fame and financial resources. This early marriage, characterized by a mix of naivety and impulsivity, set the tone for her subsequent relationships, drawing attention to the pressures faced by young stars in Hollywood.

In a turn of events that caught the media’s attention, Barrymore married comedian Tom Green in 2001. Their relationship was filled with humor and creativity, as both appeared in projects like “Freddy Got Fingered” and “Charlie’s Angels.” However, by December 2001, Green filed for divorce, finalizing it in October 2002. During this time, Barrymore expressed feelings of disillusionment regarding love and relationships, famously stating that she had stopped “believing in happy endings.” Despite their split, Barrymore and Green managed to maintain an amicable relationship, showcasing her ability to pivot gracefully in the face of personal challenges.

For nearly a decade following her marriage to Green, Barrymore dated without committing to marriage again. She had a significant five-year relationship with Fabrizio Moretti, the drummer of The Strokes, from 2002 to 2007. Following that, she entered into a relationship with actor Justin Long, which ended in 2008.

In 2011, Barrymore began dating Will Kopelman, an art consultant and the son of Chanel CEO Arie L. Kopelman. Their relationship quickly progressed, resulting in an engagement during the holiday season of that same year, and they married on June 2, 2012. The couple welcomed their first child, Olive, later that year, and their second child, Frankie, in 2014. However, in 2016, Barrymore and Kopelman announced their separation, finalizing their divorce within months. Despite the end of their marriage, the pair has remained committed to co-parenting and has maintained a cordial relationship, with Barrymore even choosing to live nearby for the benefit of their children.

As fans continue to root for Drew Barrymore, her intriguing romantic narrative is emblematic of broader societal trends regarding love and relationships in the public eye. With the rise of social media and increased scrutiny from fans and critics alike, celebrities like Barrymore navigate the complexities of romance under the glaring spotlight.

Looking ahead, Barrymore’s relationship journey offers valuable insights into personal growth and resilience. As she continues her successful career and raises her daughters, one wonders whether future romances will alter her narrative or if she will remain focused on her family and career.

The current cultural landscape also shows a growing acceptance of fluid relationships, which could influence Barrymore’s choices moving forward. Whether she chooses to embrace new love or invest in her existing friendships, her fans will be cheering her on every step of the way.

Drew Barrymore’s history of love, loss, and renewal underscores the beauty and complexity of human relationships, serving as an inspiring reminder that every ending can lead to a new beginning.