Jennifer Lopez, the multi-talented singer, actress, and businesswoman, has had a rollercoaster love life that has been as high-profile as her career. Over the years, Lopez has been engaged an astonishing number of times, each proposal more glamorous than the last. Here’s a deep dive into the engagements of one of Hollywood’s most iconic stars—you might be surprised at just how many times she’s said “Yes!”

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1. Ojani Noa (1997)

Lopez’s first engagement came from her then-boyfriend, Ojani Noa, a model and waiter. The two met in the late ’90s, and Noa proposed with a stunning marquise-shaped diamond set on a gold band. The couple married in February 1997, but the marriage was short-lived. They divorced just 11 months later, finalizing their separation in January 1998. Although their marriage was brief, it marked the beginning of Lopez’s journey through a series of high-profile relationships.

2. Cris Judd (2001)

Lopez’s second engagement came a few years later with backup dancer Cris Judd. The two met on the set of her music video for “Love Don’t Cost a Thing” in 2000. Judd proposed with an elegant emerald-cut diamond set on a yellow-gold pavé band, a symbol of their brief but intense romance. The couple tied the knot on September 29, 2001, in a private ceremony in Calabasas, California. However, their marriage was equally short-lived, with Lopez filing for divorce in July 2002, finalized in January 2003.

3. Ben Affleck (2002)

Perhaps one of the most talked-about engagements in Hollywood history was Lopez’s relationship with actor Ben Affleck. After meeting on the set of Gigli, Affleck proposed with a jaw-dropping 6-carat radiant-cut pink diamond ring from Harry Winston, estimated at $2.5 million. The ring was not only a testament to their love but also featured the word “sing” engraved, adding a personal touch. The couple planned to wed on September 14, 2003, in Santa Barbara, California, but media frenzy caused them to call off the ceremony just days before. They officially ended their engagement in January 2004.

4. Marc Anthony (2004)

Following her breakup with Affleck, Lopez quickly moved on and rekindled her relationship with her ex-boyfriend, Marc Anthony. After just six months of dating, Anthony proposed with a striking 8.5-carat radiant-cut blue diamond ring from Harry Winston. The couple married in June 2004 in an intimate ceremony at Lopez’s Beverly Hills home. Their marriage lasted a decade, during which they welcomed twins, Max and Emme, in 2008. However, the couple divorced in June 2014, marking the end of another significant chapter in Lopez’s life.

5. Alex Rodriguez (2019)

Lopez’s engagement to former MLB star Alex Rodriguez in March 2019 was yet another headline-making event. Rodriguez proposed during a romantic getaway in the Bahamas with a 16-carat emerald-cut diamond ring, estimated to be worth over $1 million. The proposal was a complete surprise to Lopez, who later shared her excitement and gratitude on social media. Despite plans to marry in Italy in June 2020, the COVID-19 pandemic forced the couple to postpone their wedding twice. Sadly, they ended their engagement in April 2021, leaving fans wondering what could have been.

6. Ben Affleck (2021)

In a plot twist straight out of a Hollywood movie, Lopez and Affleck rekindled their romance 17 years after their initial breakup. In April 2021, the couple got back together, and by April 2022, Affleck had proposed once again. This time, the ring featured a breathtaking 8.5-carat radiant-cut green diamond, flanked by two half-moon accent diamonds and set on a platinum band, valued at over $5 million. The engagement marked a new chapter for Lopez and Affleck, as they finally tied the knot.

The Final Chapter? (2024)

Lopez’s love life has been a rollercoaster, with a series of engagements that have kept fans and tabloids buzzing for years. However, her story took another dramatic turn in 2024 when she divorced Ben Affleck, marking the end of their second attempt at happily ever after.

Jennifer Lopez’s journey through love and relationships has been nothing short of extraordinary. From marquise diamonds to pink and green engagement rings, each proposal has been a chapter in the love story of a true Hollywood icon. Who knows what the future holds for Lopez? One thing’s for sure—she knows how to keep us all guessing!