News Tiffany Haddish Aggressively Hit on Leonardo DiCaprio and It Involved Role Play By Jonathan Borge Jonathan Borge Instagram Twitter Jonathan Borge is a writer and editor living in New York City. His writing has appeared in Glamour, Refinery29, Forbes, and PAPER, among other publications. Plus, he's held staff positions at Marie Claire, InStyle, and OprahDaily.com. Currently, he's the Senior Entertainment Editor at Bustle Digital Group's Elite Daily, where he oversees digital covers, features and profiles, freelance essays, and strategy for the site's TV/Movies and Celebrity and Music sub-verticals.He primarily writes about pop culture and style, and has a passion for telling LGBTQ+ and Latinx stories. When he's not working, he's likely waiting for Lady Gaga to announce her next tour. InStyle's editorial guidelines Updated on June 13, 2018 @ 02:00PM Pin Share Tweet Email Tiffany Haddish only wants one thing: Leonardo DiCaprio. And his babies. Last fall, the actress made it clear she’s looking to carry the Oscar winner’s offspring, telling Stephen Colbert, straight up, “I want to get pregnant by Leonardo DiCaprio.” Weird, but um… same? So far, the actress and comedian has had no such luck. In a new interview with The Hollywood Reporter, she explains exactly how she came on to DiCaprio when she cornered him earlier this year. If you’re looking to win over a hunk, listen up. “Yeah, I met him at a party two, three months ago, and I asked him if he’d let me hit that,” she said. “He’s like, ‘Tiffany, you’re so funny.’ I’m like, ‘I’m serious.’ And then he goes, ‘I mean, I’d do it, but …’ I was like, ‘Come on, wasn’t you in a squad? The coochie squad? Or something?’” Haddish was referring to the “pussy posse,” a group of then-up-and-coming Hollywood favorites like Tobey Maguire and magician David Blaine who stayed out late and partied with girls in the ‘90s. A theory as to why he may not be interested? While Haddish is young at 38, she doesn’t quite match up with the average age of the women he likes to romp around with: 22.9. That didn’t stop her from pushing him, going so far as to suggest some role play. The Hottest Short Haircuts of Summer 2018 “I told him, ‘My only stipulation: I wanna do it with you as your character in What’s Eating Gilbert Grape.’ He starts bustin’ up laughin’. ‘Why?’ he asks, and I say, ‘Cause I feel that performance deserves a real reward and that reward is this [gestures at her own body].’” Haddish said. DiCaprio’s role in the film earned him his first Oscar nomination at 19—but no win. “He starts goin’ into how he got into the role, how he worked with these kids and all this stuff, and I’m just listenin’ and listenin’, like, ‘Mmm-hmm, mmm-hmm.’ I finally go, ‘All that’s good, I just need to know, When’s this gonna happen?’” Time’s ticking, Leo.