Tobey Maguire and Jennifer Meyer divorced in 2016. He hasn’t remarried, and I get the feeling that he and Meyer actually have a great co-parenting relationship and they’re still pretty good with each other. Since his divorce, Tobey has dated a few much-younger ladies. His dating patterns have not been as egregious as his bestie Leo DiCaprio’s patterns, but yeah, Tobey absolutely goes for much younger women. This is something else though. Tobey was spotted outside of Michael Rubin’s annual 4th of July party, and Tobey was apparently leaving the party with his new girlfriend (???) Lily Chee. She’s barely out of her teens. Tobey just turned 49 years old last month.
Tobey Maguire spent time with actress Lily Chee at the star-studded White Party on the Fourth of July. The Spider-Man actor, 49, was photographed with his arm around the model-actress, 20, at Fanatics CEO Michael Rubin’s annual Independence Day party in the Hamptons, New York.
The pair followed theme in all-white outfits to the summer bash, which was also attended by Machine Gun Kelly, Megan Fox, Drake, Megan Thee Stallion, Kim and Khloé Kardashian, Tom Brady, Rob Gronkoswki, C.J. Stroud, Quavo, Druski, Megan Thee Stallion, GloRilla, Emily Ratajkowski, Lil Wayne and more.
Chee shared a video and photo seemingly taken at the party on her Instagram Stories. The photo showed her gathered with a group of people under pink-colored light; she included a fireworks emoji with it.
Reps for Maguire and Chee did not immediately respond to PEOPLE’s requests for comment.
I’ve never really paid attention to Lily Chee but I know she can do better than Tobey Maguire. She’s a model, actress and she has a significant social media presence and following. Seabiscuit came out the year she was born. Lily was less than a year old when Spider-Man 2 came out. Lily was born three years before Tobey’s daughter Ruby was born. Yeah… let’s not. Hopefully this is nothing and everyone just… moves on.
Photos courtesy of Backgrid.
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- Beverly Hills, CA – Spiderman star, Tobey Maguire, spotted leaving Funke restauarnt in Beverly Hills where he dined with Leonardo DiCaprio and friends. Pictured: Tobey Maguire BACKGRID USA 12 APRIL 2024 BYLINE MUST READ: JAST / BACKGRID USA: +1 310 798 9111 / usasales@backgrid.com UK: +44 208 344 2007 / uksales@backgrid.com *UK Clients – Pictures Containing Children Please Pixelate Face Prior To Publication*
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- New York, NY – 49-year-old actor Tobey Maguire may be taking some dating advice from best pal Leonardo DiCaprio! The Spider-Man star was seen with 20-year-old Lily Chee on his arm at Michael Rubin’s star-studded 4th of July bash yesterday. Pictured: Tobey Maguire, Lily Chee BACKGRID USA 5 JULY 2024 BYLINE MUST READ: BlayzenPhotos / BACKGRID USA: +1 310 798 9111 / usasales@backgrid.com UK: +44 208 344 2007 / uksales@backgrid.com *UK Clients – Pictures Containing Children Please Pixelate Face Prior To Publication*
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- New York, NY – 49-year-old actor Tobey Maguire may be taking some dating advice from best pal Leonardo DiCaprio! The Spider-Man star was seen with 20-year-old Lily Chee on his arm at Michael Rubin’s star-studded 4th of July bash yesterday. Pictured: Tobey Maguire, Lily Chee BACKGRID USA 5 JULY 2024 BYLINE MUST READ: BlayzenPhotos / BACKGRID USA: +1 310 798 9111 / usasales@backgrid.com UK: +44 208 344 2007 / uksales@backgrid.com *UK Clients – Pictures Containing Children Please Pixelate Face Prior To Publication*
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- New York, NY – 49-year-old actor Tobey Maguire may be taking some dating advice from best pal Leonardo DiCaprio! The Spider-Man star was seen with 20-year-old Lily Chee on his arm at Michael Rubin’s star-studded 4th of July bash yesterday. Pictured: Tobey Maguire, Lily Chee BACKGRID USA 5 JULY 2024 BYLINE MUST READ: BlayzenPhotos / BACKGRID USA: +1 310 798 9111 / usasales@backgrid.com UK: +44 208 344 2007 / uksales@backgrid.com *UK Clients – Pictures Containing Children Please Pixelate Face Prior To Publication*
The thing is that being constantly around people who do morally questionable things can make your morals questionable.
I would not be shocked if he starts dating 20 year olds.
That first picture looks like Mr. Maguire has had some work done! Gotta stay young!
I like my men like I like my Spanx: tight and shiny
I think male celebs do what the rest of the male population would do if they had the money and resources. Men are so predictable and gross. It is far more shocking to see an actor date a woman age appropriate. What could they possibly have in common? I am 40 and have teenage children. I cannot understand half of the lingo they use. I cannot imagine trying to date someone over half my age and trying to have a conversation with them.
I don’t think he’s interested in her for talking.
😂 🎯
Re: dating a twenty something – he’s a douche. I recall reading about him being an entitled a-hole. My god. It’s like it’s so terrible to have to be nice to non famous people.
It’s great that he can pull it together for his kids. Low bar.
The Leonardo Di Caprio jokes have normalised this so much that it’s now no longer surprising.
20yo is a child, not fully developed. She can’t even drink. It is far from normal. 30 y gap is okay if one’s 100 and the other is 70. This is disturbing on so many levels. I do not want it normalized.
A 20 year old is not a child and can we please stop infantilizing women. He’s famous and spends a lot of time on yachts with his famous friends. Maybe she likes the lifestyle. Or better yet, maybe, just maybe, she likes him.
I assume @Mil is referring to the (well-established) fact that brains go through a massive development stage from about age 20-25 that is only matched in scope (in terms of how major the developmental changes are) by the brain development growth from ages 0-5.
So it is fair to say a 20 year old is not fully developed, from a psychological/developmental perspective, without being infantilizing – it’s true for all, not just women.
Couldn’t disagree with Aerie more. I disagree heavily with an older adult of 35+ anyone younger than 26 whatever their gender, and the 20+ year age gap at this stage of life is particularly egregious. The fact that brains aren’t fully developed until 25, these folks are basically teenagers developmentally (and in the case of 20 year old, they were actually a teenager very recently), and there is a massive power and wealth differential is just awful. Horribly abusive.
Age gap relationships start to be okay once you get to be an older adult. Basically anyone over 25 – and especially 30 and up – is an established adult with a full developed brain, and can reasonably seen as an equal making a good decision.
But a 49-year old father of multiple kids dating a 20 year old just 3 years older than his eldest kid is just awful. I’ll never be okay with it, whatever the gender. And that isn’t infantilizing. A 20 year old just isn’t mature, experienced or worldly. I’m sorry. We should shame anyone not in their 20s dating someone so young. Period.
@Aerie: It is a scientific fact that the (young) adult brain is not fully developed until 24-26; it is most associated with the parts of the brain that deal with decision making, consequences, etc.
On a personal note, I can say that I (unwisely) got involved with someone when I was 20 and he was in his 30s. I was being groomed & abused verbally/psychologically; I had no idea “what I was doing wrong to deserve” his outbursts & criticisms (as he explained it to me). My 30yo brain looked back (after a lot of therapy) and said, “That was not healthy for you.” At 40, 50 and now even 60, I look back and am glad I did the work so that I could look at myself in a loving, healthy way. I simply had no barometer or experience or maturity to handle the situation. One over-simplified explanation is that when men do this type of thing (date a 20yo when they are nearly 50) it is because they know their $hit won’t fly/be tolerated by a fully-emotionally mature woman of 30 or 35.
« Just likes him » lol
He’s a decent actor but he has always creeped me out – she can do way better than him. Run Lily run!
His ex-wife commented on someone’s question that they are not dating, they are friends. I don’t know why 49 years old man would be friends with someone at his daughter’s age and it is always a girl they are friends with, never a young man. Anyway, I am happy at least we started to question this type of behavior because I remember the times when most people would defend it as it is legal.
I’m certain his ex-wife said that to try and save her and her children the extra bad publicity of getting drug into the news cycle. He’s in no way “friends” with a 20 year old model.
Yeah, it was weird people went to her page about her ex-husband. Why would she be responsible for his actions? Of course, he would tell her they are friends. He knows that the times are changing that he can’t come out proudly about dating someone at her daughter’s age.
You brought up a good point. Why is it more often than not we see older men hanging out or becoming friends with 20yr old woman it’s seen as “she’s an adult she can choose, its fine” but if a 50yr old man was hanging out or becoming friends with a 20yr old man, we would clock it and think the dynamic was weird. The 20yr old man can still make his own decisions yet something would seem off.
I haven’t really been able to look at or enjoy his work ever since it became known that “player X” in MOLLY’S GAME was him.
Also, this is ick, whether they are dating or “just friends.” She’s still significantly younger than their actual age gap so 😬.
Yeah that story about him made me greatly dislike him.
He’s 2 years older than me, a 20 year old seems like a child to me. I hope this isn’t for real.
He’s a year older than me and a 30-year old seems like a child to me!
My brother (mid-40s) has dated a string of 23- and 24-year olds and they are so, so young. It’s hard to hold a conversation with them. All it says to me when a man dates someone so young is that no woman with a fully-formed brain would put up with him.
I’m 2 years older than him and had to pause when a 34-year-old asked me out. I can’t imagine dating/being friends/whatever with someone not even old enough to drink!
Eheheheh. He played a freshfaced-but-scumbag American soldier in The Good German, and at the time I was wondering how he pulled off someone so awful. Looks like he wasn’t acting…
The term ‘star studded’ seems a bit of a stretch in the party description. Sure I’ve heard of all those people but it’s an interesting mix of names to be associated with (other than Megan Thee Stallion who is listed twice for some reason).
His ex Jen Meyer stood up for him on her Instagram comments. Saying he was walking her to her car….
So she will be very shocked when it turns out (sooner or later) that they are lovers.
It’s honestly gross. My nephew is turning 20 next month, and we are literally teaching him how to conduct himself in interviews, how to use a credit card, how to dress in things that aren’t sweat pants, and other basic adulting skills. 20 is still a child in this day and age. The idea that a 49 year old man would have a fulfilling relationship with a child is hard to fathom.
Zero knowledge of these two people and their relationship.
General questions though: As long as everyone is being treated well and no one is being controlled or taken advantage of – especially considering the isolation of COVID and epidemic of loneliness – maybe as far as age difference goes, it’s irrelevant if people are happy because love, friendship and companionship are positive things? Life is short and can be hard and if people are finding others to spend time with in a way that is good for them both, why wouldn’t they? Not sure we judge people for this?
That said, age differences can present unique challenges to romantic relationships and those can change at different points in life. An age difference that is not an issue for two people during one time period may be very difficult for them at another. Sometimes people decide it was fine in the past and might be ok far in the future but is untenable in the present.
What are you going on about?
F.Y.I she was only 16 in 2020 he was 45
What kind of equal partner can someone be when they are just starting their adult life? Now looking back, I was a baby in my early 20’s, but I thought I knew everything. There is a reason old men go after young adults. They want inexperienced partner that they can manipulate easily. There is no other reason for dating someone that young. If she was 30, she would be still young for him, but it wouldn’t be predatory. As someone in her 30’s, when I look at teenagers, early 20’s people, all I see is they are babies. He sees that too as a 49 years old man and it is disgusting that is attractive to him.
Also, as a note, usually when the younger partner gets to the older partner’s age, they see the situation differently, because they understand how young they were and how their older partner should have known it was wrong. A lot of singers wrote songs about this when they got to their ex’s age and saw the predatory side of their relationship with experienced eyes.
Our relationships don’t occur in sociological vacuums. I remember being a kid in the early 2000’s listening to women talk about Mr. Big on Sex and the City being an excellent example of a man with commitment issues you can “tame” who just needs the right woman. Only now in our popular discourse can we examine his behavior for what it was, stunted and pretty much emotionally abusive. The idea of older men and younger women is as old as time – but it has always been on a basis of an inherently misogynist culture. Conversations can help these matters, yes, I believe.
People who are of age and consenting can do whatever they want. Unfortunately for many men (not all, no, but many, many men), relationships are transactional even in their interpersonal facets (let’s examine the statistics about men being unhappier single than women, women being the one to shoulder the emotional burdens and expectations, men who leave women when they get major health issues, etc). What can they expect to get from it? We can see what Tobey Maguire would be pursuing, in a woman nearly his daughter’s age, IF he isn’t just walking her to her car as is reported, lol. Maybe examining that motivation would be helpful?
I agree with your second points. Age differences are important, but stages in life are too. I think it’s no coincidence that we discuss age differences when someone is legally an adult but still in their formative years. In fact, I think that the fluidity of this situation warrants more scrutiny. There are lots of relationships people might write off as being legal and therefore not worthy of being considered harmful. But is that actually true? It depends.
Many middle-aged men love this murky area. They are not old enough to drink legally, five years from being able to rent a car, and their brains are not fully developed. Not experienced enough to know game. Many not yet jaded.
My niece went to high school with her. They weren’t in the same friend group but the whole class knew each other. Everyone at their old high school is surprised and completely grossed out by this. At least my niece and her friends know this is soooo wrong for soooo many reasons!
EDIT: a year ago I was at their high school graduation- YUCK!!!
Going by this photo, it looks like they barely know each other. I don’t know, I’m just somehow surprised that Tobey is 49. I still picture him as geeky, goggle-eyed Peter Parker. Has he done anything in the past 10 years?
He was the creepy dark-side-of-Hollywood underworld power broker in Babylon a couple years back. And he’s done a couple of car commercials spoofing being a spoiled celebrity…
I just can’t with him since Molly Bloom confirmed what a sociopathic asshat he is.
In poker he’d try to win it all (meaning millions in a game) not because he liked poker, but because he liked to “ruin lives.”
Remember that available men often have yucky baggage by this age and age-appropriate women are fully aware and don’t want to mess with them. I have a 60-year-old long-ago-ex who I wouldn’t touch, even though it’s easy to see how old friends might renew relationships as the dating pool shrinks. Except he had a marriage to a high-profile woman and he cheated with the nanny and wrecked two marriages. I won’t even maintain that friendship because of the mess. It would taint me. So some of these guys can only date young women who actually have to more to gain in visibility and clout. I think this gal is getting more out of it than Tobey.
These entertainment guys can get into WAY messier messes than your average dude.
Waiting for the inevitable interview where she comments that she is an “old soul” and “he’s more sophisticated than guys my age” and “she would be in love with him even if he was a penniless nobody” and that they have so much in common because she was born in 2003 and that was the same year he met his first wife.
Let’s hope he is just seeing her as one of his kids and making sure she gets to her car safely.
But for some reason I think that hope is a fools errand and this thing is just wrong and disgusting.
Why are people making it out that they want a relationship? Most likely it was a hookup after a party, hit and quit it. People hook up after parties. Big deal. They are both adults
I liked Tobey as an actor and wondered why his career tanked after The Great Gatsby but then all the poker stories about Molly Bloom gave me the ick! Imagine demanding that Molly get up on a table and bark like a seal to earn a $10000 chip? Loved it when she told him to shove it!
Hmm, I’ve always wondered if he got that Gatsby gig just because he was Leo’s friend. He’s not the first actor that comes to mind when you think of Nick Carroway.
So I’m guessing he orders her a Shirley Temple?
ICK.
A friend’s ex-husband is 57 and dating a 23 yr-old. Their daughter is the same age. I was discussing with the 55 yr-old husband of friend, also 55, and he said “Good for him. No offense, but if I ever got a divorce, no way I would be dating women in their 50’s.”
I mean, there are a lot of men who would do the same thing if they had a chance. That doesn’t mean there aren’t good men out there. Even though how much they try to normalize this with legal talk, it isn’t normal. No good father would want their young daughter to date someone old enough to be their father.
Both those men are disgusting and I’m in my early 30’s. Gotta say if I was a wife and heard that I’d nope out, even if it’s hypothetical.
Toby went right back to his wolf p*ssy posse ways after his divorce. This just screams midlife crisis