I’m afraid I’d be the ultimate hypocrite if I disapproved of Leo and Tobey lusting after young women. I don’t care, as long as the women are into it.
I’m just linking to good picture galleries of both women.
There’s no denying that the old fellas have good taste.
Example (Lily):

Despite my words above, I have to admit that Lily actually looks about 12, which is maybe kinda creepy on Tobey’s part, if they are actually dating.
By the way, both Spidey and Gatsby will turn 50 on their next birthdays.

Lily just has a baby face. She’s pretty tall. And considering she got famous at 12 as young Elektra, she has definitely, ahem, grown since then.
Oh, and I don’t buy that she’s with Tobey. She’s a VERY hot commodity in modeling. Acting is a hobby now. Tobey would be a big step down for her. She’s too busy globetrotting making obscene money and partying all over the planet. If you watch her Instagram, it’s surprising to see her on the same continent two weeks in a row, always in the budget of one fashion house or magazine or another.
Makes sense she’d know Tobey, likely end up at a lot of the same events. But she’s never had a public relationship. I’d buy that he’s a buddy who kind of keeps the creeps away. Can only imagine how many men hit on her a night.
She is taller than Spidey when she wears heels.
I don’t think there is any evidence that they are dating. I think they just happened to run into one another at that white party, and the gossip sites took it from there.
But, to quote J.B. Smoove, you know he tried to tap dat ass.
And they left the party together, so maybe he succeeded.
“They aren’t seriously dating but have been hanging out,” reported US Weekly. I think that’s celeb speak for “They aren’t in love, but they are fucking.”
At any rate, whatever they were doing, they seem to be doing no longer.
If I were she, I would not be counting on an acting career. She seems to have gone to the Matt Latanzi Acting School.
She was great as a kid in Daredevil, but the role wasn’t huge.
Doesn’t matter, she’s clearly focused on modeling. I mean, why not, when you’re making Cindy Crawford money hawking every expensive commercial item in the world?
I started following her after Daredevil because I thought she’d become a great performer with time. But then she’s suddenly “I’m 17 and being paid more money than I’ve ever seen to spend a week in Bora Bora lounging around in he finest swimsuits the world has OMG!!!” That will change your priorities really quick.
I don’t see her with Tobey. He’s a nerd. She’s a mermaid (if she’s not in the water half of a week she’s unhappy) so I think she’s more tanned and surfing instead of pale and pasty.
I can TOTALLY see her seeing an older guy she knows through his ex wife at a gathering like that and saying “there are like three guys here who are living in my thong, can you escort me outta here???”
Step down? Tobey Maguire is reported to be worth around 75 million. Try explaining to women that that is a step down.
She’s making a TON of money, and is only 20. Just getting started. No habits and smart, involved parents. $75 mil is just a good head start for someone like her, not worth getting tied up with an aging actor of middling popularity.