The 38-year-old actress and comedian has revealed that when she met the Hollywood hunk at a party a few months ago, she was bold enough to ask him if they pair could spend the night together.
Tiffany claims Leo thought it was a joke at first, but returned her flirtatious comments after she referenced the ''p***y posse'' - his famous friend circle in the 90s, which also included Tobey Maguire and Kevin Connolly.
She said: ''Yeah, I met him at a party two, three months ago, and I asked him if he'd let me hit that. 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?'''
The 'Girls Trip' star continued to joke with the 43-year-old actor about the concept of them sleeping together, and told him she would only agree to the night of passion if he did it in the style of his character Arnie from 1993 movie 'What's Eating Gilbert Grape'.
She told The Hollywood Reporter: ''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 like that performance deserves a real reward and that reward is this [gestures at her own body].' 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?'''
Leo isn't the only Hollywood start who seems to have had their eye on Tiffany either, as during the Oscars earlier this year, she teased that Brad Pitt had offered to sleep with her if they were both single in a year's time.
She said: ''Oh I just met [Brad] in the elevator! He said in one year, if I'm single and he's single, we're gonna do it. So you know what that means!''
When questioned why the pair have to wait a year before seeing if sparks fly between them, Tiffany revealed she was just as confused.
She said: ''I don't know, he told me to wait a year.''
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