Everything To Know About Ben Affleck’s Dating History As Jennifer Lopez Files For Divorce; Find Out

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Reflecting on Ben Affleck’s tumultuous love life, I find myself awestruck by the rollercoaster ride that his heart has been on. From brief flings to long-term relationships, his romantic escapades have not only captivated the public but also seem to have significantly influenced his personal growth.

Ben Affleck’s romantic life has been a matter of public interest for quite some time, ranging from his high school sweetheart to high-profile relationships with prominent actresses. Now, as Jennifer Lopez files for divorce from Affleck, it presents an ideal opportunity to delve into the intricate dating history that appears more like a rollercoaster ride through Hollywood romance.

Early 90s summer camp love: Cheyenne Rothman

Before Ben Affleck became a prominent figure in Hollywood, he had a significant relationship with Cheyenne Rothman. This romance blossomed while they were both students at Cambridge Rindge and Latin School in Massachusetts. Their bond formed at a summer camp in the early ’90s, a time when Affleck was just starting his career in acting. During those exciting years of rising fame, Rothman served as one of the stabilizing forces in Affleck’s life. She would later carve out her own path and become a film director herself.

At the 1997 debut of Chasing Amy, they were often seen together on the glamorous red carpet. However, their romance crumbled under the pressures of Hollywood stardom, leading them to part ways. Despite Affleck’s attempts at reconciliation, Rothman opted for a different route: one that steered clear of the limelight.

Currently, she resides contentedly in California together with her spouse and their trio of adolescent sons. Away from the limelight of Hollywood, she discovered a sense of satisfaction.

The Gwyneth Paltrow era

Following his split with Cheyenne Rothman, Ben Affleck then began dating the renowned Gwyneth Paltrow in 1997. Their romance swiftly became tabloid fodder as they starred together in not one but two films, “Bounce” and “Shakespeare in Love,” making them a scorching hot item in Tinseltown.

Over the course of three years, their connection was like a thrilling rollercoaster ride, filled with multiple splits and reunions. Yet, in the future, Paltrow would look back on that relationship with great warmth.

In 2015, she expressed on Howard Stern’s show that he was intelligent and gifted but not mentally prepared for a long-term relationship at that moment. Despite the split being friendly and courteous, it marked the end of a significant phase in both their lives as they each embarked on distinct journeys afterward.

Ben Affleck + Jennifer Lopez = The Bennifer 

Following his romance with Paltrow, Ben Affleck encountered Jennifer Lopez on the set of Gigli in 2001. At that point, Lopez was legally married to her second husband, Cris Judd. Their relationship remained private until her divorce became official in 2003. The public soon learned about their romance, and it quickly gained significant media attention, culminating in Affleck’s proposal with a stunning 6.1-carat pink diamond ring in November 2002.

Back in September of ’03, I was counting down the days to the wedding of my idols, yet the media frenzy surrounding their union swiftly turned it sour. Just a few days before the big day, they postponed the ceremony, citing unbearable media attention as the cause. By January ’04, their fairy-tale romance had crumbled. In her 2014 memoir, True Love, she confessed that experience was her first taste of heartache on a grand scale.

A new chapter with Jennifer Garner

Ben Affleck and Jennifer Garner’s romantic relationship was characterized by a strong emotional connection and an understanding that didn’t require words, often nurtured within their family-centric lifestyle. They initially crossed paths on the set of Pearl Harbor in 2001, and reconnected on the set of Daredevil in 2003.

As someone who has witnessed many relationships unfold over the years, I can confidently say that this particular union was a fiery one. The chemistry between them was undeniable, yet it was complicated by the fact that both were already involved with others at the time. Despite the obstacles, their romance blossomed quickly, reaching a climax in April 2005 when they quietly became engaged. Their decision to tie the knot came just two months later in a private ceremony held in Turks and Caicos, where they exchanged vows as husband and wife. Looking back on their story, I can’t help but admire their courage and determination in pursuing love against all odds.

The family consisted of three kids: Violet Anne (born in 2005), Seraphina Rose Elizabeth (born in 2009), and Samuel Garner (born in 2012). After ten years together, they renewed their wedding vows in a private ceremony. However, after a decade, they announced their separation, emphasizing that their primary focus would always be their children.

Despite their separation, Affleck and Garner reportedly maintained a close relationship, with her providing significant aid during Affleck’s fight against alcohol addiction. Affleck himself has expressed deep regrets about the divorce, once calling it “the greatest mistake” of his life. However, in 2023, he clarified to The Hollywood Reporter that his alcoholism issues were self-inflicted. Despite the divorce, they continue to hold mutual respect and care for one another.

Lindsay Shookus and the struggles with busy schedules

In 2017, things between Ben Affleck and his Saturday Night Live producer girlfriend, Lindsay Shookus, became significant. However, their busy schedules made the relationship unstable, leading to an off-and-on pattern. Eventually, they parted ways in 2019, with their hectic lives being a major contributing factor. Despite their breakup, Shookus continues to be one of Affleck’s notable romantic interests.

Brief connection with Shauna Sexton

2018 saw Affleck having a short-lived romance with Shauna Sexton, a vet tech and former Playboy model. Despite its brief duration, their relationship stirred curiosity due to the significant age difference between them. The relationship fizzled out quietly, yet it continued to fuel public interest in his personal life.

Pandemic romance with Ana de Armas

Affleck and Ana de Armas’s relationship started on the set of Deep Water, which later turned into a widely publicized affair. The most conspicuous phase of their romance unfolded during the pandemic, as nearly every day, photos emerged of them enjoying strolls and laughing in Los Angeles.

Despite appearances suggesting all was well, their relationship apparently concluded in January, with conflicting future plans being the apparent cause. According to insiders who spoke to Page Six, de Armas was eager for a deeper commitment, such as expanding their family, but Affleck’s aspirations were quite different.

The Return of Bennifer

Once more, Ben Affleck returned to familiar grounds as he reconnected with Jennifer Lopez. It’s not a stretch to say this wasn’t just a coincidence, given that around the same period, Lopez was wrapping up her engagement with Alex Rodriguez. A source revealed to E! News they had maintained contact throughout the years, leading to several dinner meetings.

By May 2021, they managed to take a trip to Montana amidst their busy schedules, which was arranged by Affleck, according to E! News. Sources close to Lopez mention that she is greatly impressed by how much Affleck has evolved, referring to him as a more advanced version of the man she used to know.

The pace of their relationship was swift, and by the month of July, they were blending families at Universal Studios. Rumors of a second engagement had been circulating since August, following sightings of them shopping for rings. However, it wasn’t until almost a year later that Lopez herself confirmed this news in her newsletter, On the JLo.

In a private ceremony held in Las Vegas during July, the couple officially got married. Lopez shared her feelings about this special event in another newsletter issue, describing it as overflowing with love and emotional depth. She further demonstrated her commitment by adopting Affleck’s surname and showcasing her wedding ring on Instagram.

Refreshed by the revitalized bond, Lopez stepped into the recording studio to commence work on “This Is Me, Now” – a follow-up to the 2002 album bearing the same title, which chronicled their initial romance.

Following this remarkable turnaround, however, the initial signs of strain in their relationship started to emerge. Their low-key outing at a school play in May was their first public appearance since March, with Lopez cancelling her This Is Me. Live tour and adding fuel to the speculation about their troubles.

As the murmurs grew stronger, it became evident that our reconciliation wouldn’t have a fairy-tale conclusion like in movies. The decisive moment arrived when Lopez filed for divorce on August 20th, marking April 26th as the day we officially parted ways, signaling the end of an era that captivated millions of fans across the globe.

In the present, Affleck is trying to understand this new phase in his romantic journey, which has been a blend of high-profile romances, intense public attention, and personal evolution. Each relationship he’s had has left an indelible impact on him, contributing to the intriguing tale of one of Hollywood’s most discussed personalities.

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2024-08-22 20:14