Hill, known for his roles in films like Superbad, The Wolf of Wall Street and 21 Jump Street, was first spotted with Santos, a content manager for a beauty brand, in New York City in August 2018. Though they’ve tried to keep their relationship out of the public eye, the engagement isn’t a complete surprise. Just before the news of Hill’s proposal broke, Variety reported that the actor-turned-director purchased property in Santa Monica, California, close to where his girlfriend is based.
Santos also appears to have gotten the stamp of approval from Hill’s family. She’s included in multiple family photos shared on Instagram by Hill’s mother, costume designer Sharon Feldstein.
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The birthday boy is contemplating his next move . Richie is smiling because he’ll be home by 730. @dfeld1025 forgot to open her eyes. @beaniefeldstein @joshfeldstein1211 @gianna__santos @jonahhill all look great . And I’m still looking for a hair collaboration. @gregoryrussellhair @georgepapanikolas
In October 2018, two months after publicly stepping out with Santos, Hill opened up to Complex about his desire to keep his personal relationships private. “With a relationship, there’s no control, because there’s a person that’s not you,” Hill said. “For me—why work is easier than that stuff—is because I know if I work hard enough…I’m in control of it working. I think relationships are scary in that way.”
While the couple has yet to publicly announce the engagement, Santos was spotted wearing an engagement ring while out with Hill over Labor Day weekend.