Jennifer Lopez married waiter-turned-restaurateur Ojani Noa in 1997 and the two divorced less than a year later.
Noa proposed with what appears to be a pear-shaped diamond ring, worth an estimated six figures.
The multi-hyphenate and her former back-up dancer Cris Judd wed in 2001. The two split less than a year later and finalized a divorce in January 2003, while she was engaged to Ben Affleck.
Judd popped the question with this emerald-cut diamond ring, estimated to be worth six figures.
Kicking off a romance in 2002, Lopez and the actor filmed famous flop Gigli, the movie Jersey Girl and the singer's "Jenny From the Block" music video.
That November, Affleck proposed, with the two planning on having a wedding ceremony in Santa Barbara, California, on Sept. 14, 2003. Affleck called it off four days beforehand, citing "excessive media attention." In January 2004, the two publicly ended their engagement.
Affleck gave his bride-to-be a 6.1-carat pink radiant cut diamond Harry Winston ring, estimated to be worth between $1.2 and $2.5 million.
Lopez and fellow singer Marc Anthony, who share twins Max and Emme, wed in 2004 and announced their split in 2011. Anthony filed for divorce a year later and it was finalized in 2014.
Anthony proposed to Lopez with an 8.5-carat blue diamond Harry Winston engagement ring, estimated to be worth $4 million.
Having reconnected in 2017, former New York Yankees standout Alex Rodriguez swung for the fences, getting down on bended knee on the beach during their March 2019 trip to the Bahamas.
In April 2021, J.Lo and A-Rod called off their engagement.
The 15-carat emerald-cut diamond engagement ring Rodriguez chose is estimated to be worth between $1 million and $5 million.
The two rekindled their romance in spring of 2021. On April 8, 2022, she revealed in her On the JLo newsletter that they were engaged. But after a 2022 Las Vegas elopement—followed by fairytale vows in Georgia months later—she filed to end their nearly two-year union.
For the second go-round, Affleck went for a hue that Lopez had dubbed lucky after stealing the show at the 2000 Grammys in her iconic Verace gown. The green cushion-cut diamond was set with two white diamond side stones.