16 Crazy Secrets Behind Macaulay Culkin And Mila Kunis’ Relationship

People across the world love to read about celebrities. They help bring our favorite movies and TV shows to life and create the kinds of characters that we spend our entire lives talking about. What could be better than that?

Well, as it turns out, your parents were wrong: more is better. That means, if one celebrity is good, celebrity couples are downright great. Sometimes, it seems the entire internet could be powered by the gossip machine of who is dating whom at this very moment.

What about those power couples that slipped through your personal radar? In some cases, very surprising Hollywood elites got together and stayed together a good, long time. That’s exactly what happened with Macaulay Culkin and Mila Kunis.

You probably think you already know all you need to know about these two: she’s happily married to Ashton Kutcher and he’s busy keeping a low profile - minus some surprise musical performances. For nearly a decade, these two were in an intense relationship that basically defined what Hollywood romance can be.

Of course, you don’t just have to take our word for it.

Keep scrolling to discover 16 Crazy Secrets Behind Macaulay Culkin And Mila Kunis’ Relationship!

16 They Dated for Almost a Decade

To fans who did not necessarily grow up watching the rise of Kunis and Culkin’s careers, the very idea that they were together usually comes as a surprise. This leads many to assume that the relationship must have been brief—some sort of quiet affair that the public only finds out about long after it is over.

However, this is not the case at all: the two stars dated for over eight years, starting way back in 2002. Interestingly, this was a time in which both stars were about as famous as they would ever be.

Macaulay Culkin’s career famously peaked early as he starred in Home Alone in 1989 and Home Alone 2 in 1992. While 2002 was ten years later, his movies (and Culkin himself) were quite beloved by fans who grew up watching them over and over. Meanwhile, Kunis starred in That 70’s Show, which started in 1998 and was basically at the peak of its own fame in 2002.

This all leads to the great irony: right now, their relationship feels like an odd mismatch, but at the time, they were basically celebrity royalty with an equally frenzied collection of fans that would follow them wherever they went.

15 She Knew He Wasn’t Marriage Material

One thing that surprises many fans is just how long Mila Kunis and Macaulay Culkin were together. Their relationship lasted so long that many fans assumed that their would be wedding bells in their future. That’s why their breakup in 2011 was such a shocker.

Maybe we shouldn’t have been surprised by the lack of wedding bells. At the very least, one person wasn’t shocked at all: Mila Kunis herself! According to her, despite his many great qualities, Culkin was never quite marriage material.

In a surprisingly open interview about their relationship with Howard Stern, Kunis revealed that she had been reticent about marriage for a very long time. In fact, she recalls telling her father when she was only sixteen that she didn’t believe in marriage. Of course, with the benefit of hindsight, we know that is not completely true, as she ended up marrying Ashton Kutcher.

When Howard Stern asked her if the unwillingness to marry Culkin was a sign that she wasn’t truly in love with him, Kunis responded, “Honestly, who knows?”

Considering that Kunis and Kutcher married after only three years of dating, it seems like maybe Kunis always knew that Culkin wasn’t going to be the one she settled down with.

14 She Thought His Fans Were “Abnormal”

Celebrities often have a weird dynamic when it comes to fans. On one hand, fans are literally the backbone of celebrities’ fame and success: you can’t grow famous if no one cares about watching you!

On the other hand, fans often have a weird sense of entitlement regarding actors and the work they star in. This can lead to harassment of the stars or even a sudden shift in the ratings or box office of their work.

How did Culkin and Kunis handle their fans? Well, they handled their own fans just fine - though Kunis didn’t really like Culkin’s!

In that same interview with Howard Stern, Kunis had a great one-word description of Culkin’s fans: “abnormal.” She said that Culkin was famous enough that she couldn’t even walk down the street without fans flocking to them. Remember what we said about A-list vs. B-list.

To hear her tell it, these were not normal fans: they just started incoherently screaming when they saw him, which she told Stern was not “a normal response to a celebrity.”

She chalked this up to them just not knowing “how to react,” but it’s notable that when she looks back on their relationship, his crazy fans stand out so prominently.

13 He Was Her "Steady Rock"

Part of what makes Kunis and Culkin’s eight-year relationship so significant is how young the actors were (and, in many ways, still are). By the time they broke up in 2011, he would have been thirty and she would have been twenty-seven. Obviously, an eight-year relationship is a significant chunk of time for people who are so young.

Some fans have wondered if this shaped their relationship in a positive or negative way. To hear Kunis describe it, though, the experience was entirely positive, and their relationship helped her discover a happier place in her life.

In an old interview, Kunis points out that she was just a teenager when she met Culkin, and that it felt like they basically “grew up together.” She admits that this was part of what made the relationship special, and that she wasn’t sure if it would have been the same if they met when she was twenty-six or twenty-seven.

Ultimately, though, meeting so young was a benefit, as she describes Culkin as her “steady rock” in her life, saying “that’s all that you need.” This is likely part of why their breakup was so amicable: the two genuinely want what is best for each other.

12 He Became a Roadie After They Split

Many people have weird ways of coping with a relationship ending. For actors, one natural choice would be to throw themselves in another creative work. However, Macaulay Culkin had a unique dilemma when he and Kunis broke up: he had also taken a break (which he later called being “essentially retired”) from the world of acting. However, Culkin still had a lot of energy and creativity, and he still needed to find a way to rebound from the relationship. He did so in the last way anyone would expect: he became a roadie!

That’s right. In his own words, Culkin told The Guardian “Home is where my boots are. I’m a big fan of jumping on people’s tour buses, making myself useful, doing load-ins and outs. I do everything except the merch table. I tried that, but ... we didn’t sell anything.” He finds this a pleasant alternative to having to avoid the paparazzi wherever he goes.

It also fuels his own creative juices from time to time, as Culkin has his own unique band called Pizza Underground that performs sporadically.

They even performed in a bizarre passion project of Culkin’s: an adaptation of Aladdin that was directed by Adam Green, the Moldy Peaches singer he is sometimes a roadie for.

11 They Kept the Breakup Secret

It’s easy to get skeptical when celebrities insist a breakup was “amicable.” One of the reasons for this is that it is what everyone says: no one wants to admit how much they hate the other person, or end up looking bad by talking trash about their former partner.

How can you tell if a breakup was truly amicable? It mostly comes down to whether the two still care about each other’s feelings, which is how we know Kunis and Culkin had a truly amicable split.

As it turns out, there was a big gap in time between when they announced their breakup and when they actually broke up. In fact, there was a gap of several months. So, why all the secrecy? At the time of their break-up, Kunis was busy promoting her movie Black Swan (a movie which went on to net several Oscars).

Announcing a split in their long-term relationship might have created negative press when the movie was in theaters, and it would have caused additional stress to Kunis during an already stressful time. Keeping quiet about the breakup to make her life and career less stressful is a sure sign of the mutual respect these two shared even after they split.

10 Culkin Was Married at 18

As we talked about before, much of the discussion surrounding Kunis and Culkin’s relationship focuses on how young they were at the time. It’s part of what made their eight-year relationship so significant— their relationship formed a relatively huge portion of each other’s lives before they broke up.

However, while Culkin is just a few years older than Kunis, there were some events in his life that may have aged him a bit before his time. For instance, did you know he had an entire marriage before he and Kunis ever dated?

It’s true. When he was only eighteen years old, Macaulay Culkin married actress Rachel Miner. Nowadays, she is mostly known for playing the role of Meg Masters on Supernatural, but when she and Culkin met, she had a similar arc, with her film debut (in Woody Allen’s Alice) being in 1990 whereas Culkin’s breakout hit Home Alone came out in 1989.

The two got married back in 1998, but a long relationship was not in the cards: they separated two years later and then divorced two years after that.

While Kunis and Culkin haven’t said much about why they never married, it’s possible Culkin’s previous marriage made him not want to rush into anything.

9 He Allegedly Had Substance Issues During Their Relationship

One aspect of their relationship that is a common rumor is that it was marred by substance use. This became a topic of national concern when photos emerged of Macaulay Culkin looking frighteningly thin, causing many tabloid papers to run stories alleging substances abuse and other sordid tales.

Culkin has been understandably mum regarding the details of possible substance use, but he eventually admitted that illegal substances were once a part of his life. However, he was quick to point out that the substance use was never as bad as tabloids and paparazzi journalists claimed it was.

To set the scene, various tabloids loved to allege that Culkin had horrific addictions to pills and other substances. However, the only confirmed drug use we know of regarding Culkin came was back in 2004 when he was busted on a marijuana charge. So, what about his alleged substance abuse? The truth falls somewhere in the middle.

In a 2016 interview, Culkin pointed out he “was not pounding [illegal substances] every month or whatever,” but cagily admitted he was involved in “silly stuff” on occasion.

In a 2018 AMA on Reddit, Culkin said “yes, I consumed and imbibed [substances] in my life. Never as bad as people said.”

8 Russel Brand Tried to Butt In

While Mila Kunis had some film roles before, they ranged from “forgettable” to “outright bad.” That’s why 2008’s Forgetting Sarah Marshall was something of a breakout movie role for her. Compared to her previous roles, this movie was practically star-studded, starring Kristen Bell, Jason Segel, Paul Rudd, and a man who was quite popular at the time: Russel Brand.

Kunis and Culkin’s relationship would continue several years after this movie, but here’s a secret: Russel Brand thought about getting in the way!

Something Brand is always in a rush to remind people is that he is a ladies’ man, and he fancies adding up as many romantic conquests as possible.

When he and Kunis starred together in Forgetting Sarah Marshall, Brand thought this might be the opportunity to add her name to his list of conquests.

He soon found out she had a boyfriend, but she only referred to him as “Mac,” meaning Brand was quite surprised when it ended up being Macaulay Culkin! With his characteristic lack of subtlety, Brand would later say that Culkin was “longer and looked pale and scared of himself, like a scared horse,” and he further added “there was a horror about him.”

Culkin got the last laugh, though, as he’s looking better than ever and Brand has largely faded from public life.

7 Culkin's Rebound

There is something of an art to the romantic rebound. In a weird way, this is one of the big things that humanizes celebrities: no matter how rich and famous they are, celebrities often struggle with rebounding and come up with the same kinds of weird solutions that we do.

For Kunis, her rebound is basically public knowledge: soon after breaking up with Culkin, she was dating Ashton Kutcher, and before you know it, wedding bells were ringing. Culkin’s rebound is less well-known, and she might tell us a bit more than Culkin intended about his romantic tastes.

A couple of years after breaking up with Kunis, Culkin was dating actress Jordan Lane Price. She is a beautiful young woman, and by all accounts, she and Culkin were very happy together. However, when their relationship first became public knowledge, individuals and magazines alike commented on how Price looked shockingly like Mila Kunis.

Of course, this set the rumor mill off like little else, with many hinting that Culkin had never really gotten over his ex. We have a simpler theory: maybe Culkin just really likes beautiful brunettes? If that’s the case, is there really anyone that can blame the young man?

6 He Made a Vow of Celibacy Before They Met

For Macaulay Culkin and Mila Kunis, their early relationship often feels mythological. This is, in part, due to their own discretion: even their most hardcore fans know very little about how they got together or what their personal life at the time was like, leaving fans to speculate.

However, for these two dynamic celebrities, it’s only fitting that the truth managed to be stranger than fiction. Culkin shared a story about where he was at in his life when he met Kunis that seems simultaneously unbelievable and exactly what you’d expect from the eccentric star.

As we mentioned earlier, Culkin had been around the romantic block a bit before he met Kunis.

Specifically, he had already been married and divorced within a very short span. According to Culkin, he had some interesting ways of dealing with this: at first, he was happy to go “to clubs and bars and [flirt[ with every waitress in New York City.”

Eventually, this got old and he did the unthinkable for a single celebrity stud: he took a vow of celibacy! Culkin seemingly wanted to wait until he found the right person, and it didn’t take too long for him to meet and fall in love with Mila Kunis.

5 They Met Because of a Terrible "Sequel"

When you think about Mila Kunis and her film career, chances are that you’re thinking of one of the big movies. This might include the Oscar-winning Black Swan, the gut-busting Forgetting Sarah Marshall, and so on. However, her cinematic beginnings were much more humble, as she was the star (alongside William Shatner) of American Psycho II: All American Girl.

This movie had a weird history: it wasn’t originally connected to the first American Psycho, and Lionsgate Films added the connection later on to boost its appeal. It didn’t really work: critics tore the movie apart while Kunis later denounced the film.

Still, it wasn’t all bad: if she hadn’t starred in this terrible movie, she might have never met Macaulay Culkin!

While Culkin didn’t star in the movie, he was visiting the set of this 2002 future flop.

That was when he met Kunis, beginning a relationship that would span nearly a decade. Interestingly, this is part of how their careers' trajectory: Culkin’s career started out white hot with movies like Home Alone, but it eventually faded with unpopular films like Richie Rich. Kunis started out with terrible things like an American Psycho sequel before her career hit the stratosphere.

4 They Broke Up Because She Wanted to Be Single

“Know thyself.” This is a bit of ancient Greek wisdom that many of us still bust out to this day. As wisdom goes, it’s pretty good: it refers to our need to know what we really want and what our lives are really about. If we don’t, then we’re destined to a lifetime of unhappiness.

Obviously, this extends to the world of relationships as well, and as it turns out, both Macaulay Culkin and Mila Kunis are very good at knowing themselves. We can see that based on the reason that the two of them ended up breaking up.

As usual, the two stars were pretty discreet when they talked about why they broke up. Most of the time, they just focused on the split being amicable, how they were focused on their own lives, and so on. The closest they came to giving a direct explanation, then, was when Kunis was discussing her desire to not rush into a relationship with Ashton Kutcher.

According to her, many of their early conversations focused on the idea that both Kunis and Kutcher, coming off of really long-term relationships, needed to enjoy being single. Reading between the lines, it seems like after all that time, Kunis and perhaps Culkin as well needed some space to simply focus on their own lives.

3 They Wanted Kids But Not Marriage

Earlier, we discussed that Kunis seemingly had an aversion to marriage from a young age (though enough of an aversion to avoid marrying Ashton Kutcher). Her exact reasons for this were her own, and they seemed to change from moment to moment. At one point, she amusingly told her father she would only consider getting married when gay people could get married, situating her marital resistance as a political act.

Culkin’s reticence to get married was a bit more clear. Culkin had dealt with an abusive father and a previous failed marriage, so it was understandable that he wasn’t in a rush to settle down again.

Did this end up weighing down their relationship? Not exactly.

Part of what made them a good couple was that they shared the same weird sense of humor about a great many things, and that included marriage.

Culkin would later recall both of them joking about how they were likelier to have children together than they were to get married. In a way, this underscores a very progressive and nuanced view, as they understood that marriage is more of a social contract than an actual rule they had to follow! They were content to make up their own rules together, at least for a while.

2 Their Fame Levels Swapped

There’s an interesting distinction that many fans make, whether they mean to or not. If you were ranking Hollywood celebrities, most people end up ranking movie stars higher than TV stars. There is an idea that starring in a movie  -especially a big and expensive one - is a sign of true prestige, whereas TV shows are filled more with “working actors” - those who go from job to job.

Why are we talking about this? At the time that Kunis and Culkin started dating, they were both very popular, but to the public, Culkin was the A-list star and Kunis was the B-list star.

Eventually, the two ended up flip-flopping. While Culkin was the megastar A-lister when they started dating, he didn’t really star in too much after Home Alone 2. To put it mildly, his fame was truly resting on its laurels. Meanwhile, Kunis couldn’t be stopped: she parlayed her That '70s Show fame into hit films like Forgetting Sarah Marshall and Black Swan.

She effectively had it both ways, achieving A-lister Hollywood status while still doing a ton of TV, such as her voicework on Family Guy and Robot Chicken). Before you knew it, Kunis was everywhere you looked, and Culkin was barely anywhere to be seen.

1 They're Both With Co-Stars Now

“Opposites attract” is some pretty common romantic advice. The idea is pretty simple: that human lives are like opposite ends of a magnet and we find ourselves inextricably and inexplicably drawn toward people who are nothing like us. As advice goes, this sounds nice and sage, but the truth is, it’s wrong more often than it’s right.

The truth is that like attracts like: just as you’re more likely to be friends with people who share your interests and personality, you’re likelier to fall in love with those same kinds of people. Culkin and Kunis are no exception to this.

How can we tell? Ironically, we can detect this detail about their time together by looking at what they did once they were split up. Specifically, the two ended up dating their co-stars.

The more well-known instance of this comes from Mila Kunis: she and Ashton Kutchen famously starred together in That '70s Show before dating and eventually getting married. As for Culkin?

While Culkin’s had a very interesting romantic life, he eventually ended up dating actress Brenda Song.

As it turns out, both of them are starring in Seth Green’s directorial debut, a film named Changeland, so he’s dating a co-star as well. Even after all these years, Culkin and Kunis still share a similar way of doing things!


Do you have any other trivia to share about Macaulay Culkin and Mila Kunis' relationship? Let us know in the comments!

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