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Slide 3 of 10

November 1997: Will and Jada Pinkett Smith Get Engaged

After two years of dating, Will spontaneously decided to propose to Jada in November 2017. While talking to People in February 2005, the actor said he randomly popped the question when he and Jada were getting ready to go to sleep. "I looked over at her, and I said, 'Hey, we might be real good married. Wassup? You wanna marry me?'" Will said.

The moment was so "unplanned" that Will didn't have a ring for Jada, but that didn't deter her from accepting his proposal. "She said yes," Will said. "It's really weird when you live the kind of lifestyle that we live: simplicity becomes the jewel."


Image Source: Getty / Ron Galella