Alex Rodriguez Proposed to His Assistant 3 Times Before Asking Jennifer Lopez to Marry Him—But It’s Not What You Think

Alex Rodriguez proposed to Jennifer Lopez after two years of dating. But when he got down on one knee on a beach in the Bahamas, it wasn’t his first time.

Sure, he’s been married before, but that’s not what we mean. Rodriguez, 43, was so nervous about asking his 49-year-old love to marry him that he practiced repeatedly before popping the question for real.

The former baseball player told Jimmy Fallon all about his proposal warm-up sessions when he visited The Tonight Show Starring Jimmy Fallon last night.

After J.Lo released the song “El Anillo” (aka “the ring” in Spanish) and signed on to star in an upcoming film called Marry Me, A-Rod couldn’t help but get the hint. So, he got the ring and planned a trip to the Bahamas for them over the course of six months.

But that wasn’t all. To ensure the sunset and lighting would be just right, he practiced the proposal three days in a row with his assistant Ashley upon his arrival on the island. (We hope she got a raise after that.)

“I rehearsed three days in a row because I wanted the sunset to be perfect. So, one time the sunset was at 6:27. The next day was, like, 6:29 and then the third day it was raining,” he explained. “So, I kind of came out around 6:29, and I said, ‘This is the time where I’m going to do it’ and it worked out well.” We’d say so.

Rodriguez presented his wife-to-be with a 10- to 15-carat rock (boulder?) and she said yes. As Fallon pointed out, Rodriguez also broke out his bling-y World Series ring for the occasion.

For now, the couple is celebrating their engagement and putting a pause on the wedding planning.

One thing A-Rod knows for sure: He’s not going to dive into their first dance together without a vodka soda or two. We feel you, Alex.


Cat mom, yogi, brunch enthusiast

Lex is an LA native who's deeply obsessed with picnics, Slim Aarons, rosé, Hollywood history and Joan Didion. She joined PureWow in early 2017.