Make no mistake, 2018-2019 has been Jennifer Lopez’s biggest professional year to date. After nearly 30 years in the entertainment industry, the 50-year-old, newly-engaged singer, actress and mother took home an MTV Vanguard Award, toured the globe with her It’s My Party birthday show and gave a critically acclaimed performance as a NY-bred, take-no-prisoners stripper in new film Hustlers. “You know, I’m looking at some of these [film] reviews and thinking like, ‘OK!’ and feeling like I already won. It’s amazing. I’m not really thinking about anything else except kind of living in the moment and feeling really happy that people are loving it,” Lopez recently told ET.

But 2020 is shaping up to be even bigger. Those rave movie reviews could land Lopez a Golden Globe for Best Supporting Actress in January. The following month, she will headline the Super Bowl Halftime Show alongside Shakira in Miami. “I love that the Super Bowl has two women performing this year. That they have two Latinos performing this year,” she told FOX News. “It’s the marker of a new time, not just for the NFL but for this country. It sends an important message.”

It was in Lopez’s personal life, however, that she hit a home run. Former Yankees player and longtime boyfriend Alex Rodriguez proposed to her in the Bahamas with a 16-carat AUD$2.54 million engagement emerald-cut diamond.

“I’d like a big wedding,” she revealed in a recent video from her tour. “And I’d like to get married in a church this time.” Despite three other weddings – and four engagements – Lopez admitted she has never married inside a church.

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All five engagement rings have been either cushion or emerald cut, Lopez nodding to one major jewellery trend: non-round gemstones. Here, we dig deep into the Jenny archives and unearth her past four diamonds – and their relationship dramas.

Ojani Noa

Lopez got married to this restaurant owner when she was 27 year old. The marriage lasted just one year – but in that time, she sported a AUD $140 000 marquis-cut diamond. Things got ugly between the pair when Noa threatened to release a sex tape. Lopez took him to court and it never saw the light of day, or a VCR.

Chris Judd

This guy seemed cool. JLo met back-up dancer and choreographer Judd in 2000 on the set on her “Love Don’t Cost A Thing” music video. The pair married in 2001 but divorced two years later. Judd’s ring though became Lopez’s favourite – a six-figure emerald-cut diamond.

Ben Affleck

Yes, she moves quickly. In 2002, Affleck proposed to Lopez even though her divorce from Judd wasn’t final. Lopez broke the co-worker rule again, meeting the actor on the set of their ill-fated movie Gigli. The ring was 6.1 carats and pink and estimated to be worth AUD $3.52 million. Four days before the wedding, Affleck called it all off and Lopez was absolutely shattered. Oh, Bennifer.

Marc Anthony

Next to her relationship with her other back-up dancer Casper Smart (whom Lopez dated for five years but did not get engaged to) her most significant past relationship to date was the one with her children’s father, Anthony. The couple were married ten years – and in that time she met Rodriguez at a Yankees game! – and Anthony proposed with a 8.5 carat blue diamond worth over double Affleck’s offering. Lopez and Anthony divorced in 2015 and for the first time in a long time, the singer gave herself some time to be single. She and ARod hooked up in 2017.

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