Breaking up is hard to do. And as Clueless star Alicia Silverstone has discovered, it can also be extremely costly.

Alicia Silverstone – best known for her leading role in seminal 1990s teen movie Clueless – reportedly has a net worth of $20 million. But she is seemingly set to lose a significant chunk of this following her 2018 split with husband of 13 years Christopher Jarecki. So here’s a look at her career and the staggering settlement that will probably affect her bank balance for quite some time.

Born in San Francisco, California, in 1976, Alicia Silverstone began her showbiz career at the age of six. And after appearing in various TV commercials, her first acting role came in a 1992 episode of The Wonder Years, where she played Kevin’s dream girl. Then, a year later, she moved to the big screen with the main role of a vengeful spurned teen in The Crush.

Silverstone also picked up two MTV Movie Awards for her performance in this erotic thriller. And she soon became a regular face on MTV thanks to memorable appearances in the videos for Aerosmith’s “Crazy” and “Amazing.” These two promos then helped Silverstone to land the defining role of her career.

You see, director Amy Heckerling, impressed by Silverstone’s star quality in the Aerosmith videos, gave her the leading part of Cher Horowitz in Clueless. The loose adaptation of Jane Austen’s Emma then became a huge hit on its 1995 release, partly thanks to Silverstone’s turn as the sweet-natured high school student. She subsequently landed a contract with Columbia-TriStar worth up to $10 million.

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Yet Silverstone’s next major role came in 1997 as Batgirl in Joel Schumacher’s Batman and Robin. And unfortunately, this superhero flick, and Silverstone’s part in it, was largely considered a misfire. Silverstone even picked up a Worst Supporting Actress at the Razzie Awards for her performance. She also experienced disappointment that year when Excess Baggage, the first film released by her own production company, flopped at the box office.

So, after starring alongside Brendan Fraser in Blast from the Past, Silverstone seemingly chose to pursue more interesting and less commercial roles. In 2000, for instance, she appeared as the Princess of France in Kenneth Branagh’s adaptation of Shakespeare’s Love’s Labour’s Lost. She then appeared in indie comedy Global Heresy and took to the Broadway stage for the first time in The Graduate.

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In 2003, meanwhile, Silverstone returned to the small screen for a leading role as attorney-turned-matchmaker Kate Fox in Miss Match. And even though NBC canceled the dramedy after just one season, Silverstone still picked up a Golden Globe nod for her efforts. Then, a year later, she appeared alongside fellow 1990s teen idols Freddie Prinze Jr. and Sarah Michelle Gellar in Scooby Doo 2: Monsters Unleashed.

Silverstone continued to spice up her acting resume with supporting roles in Barbershop spinoff Beauty Shop and Stormbreaker. She also appeared in TV movie Candles on Bay Street and starred in David Mamet play Boston Marriage. Then, in 2009, the actress became a bestselling author for her vegan nutrition guide, The Kind Diet. She also launched an accompanying website named The Kind Life.

In the years that followed, Silverstone kept mixing up stage performances with smaller indie productions. But she still made the occasional mainstream picture, including 2011 teen movie The Art of Getting By. And in 2012 she enjoyed Clueless reunions with director Amy Heckerling, in Vamps, and Jeremy Sisto, with a four-episode stint in Suburgatory.

Silverstone later added to her filmography with roles in Angels in Stardust, Who Gets the Dog? and King Cobra. She also showed up in black comedies Catfight and The Killing of a Sacred Deer and played the mom in Diary of a Wimpy Kid: The Long Haul. Then, in 2018, she returned to television with a leading role in Paramount Network dramedy American Woman.

Yet despite her extensive filmography, Silverstone told The Guardian in 2015 that she actually never intended to be a screen star. She said, “I never wanted to be in movies or TV. There’s no support or schooling on what [you do] when you suddenly found yourself famous as a young woman. It was just too much for me.”

It’s perhaps not surprising, then, that Silverstone has also become renowned for her environmentalism and animal rights work. She’s appeared in commercials for PETA, for instance, and launched her own rescued pets sanctuary. She has, however, also come under fire for her views on nutrition and her support for the anti-vaccine movement.

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Silverstone nevertheless shares her passion for animal rights with Chris Jarecki. She first met the musician in 1997 outside a cinema. Jarecki would later go on to front S.T.U.N., a rock band that was briefly signed to Geffen Records. And the pair dated for seven years before he finally decided to pop the question.

In 2005 Silverstone recalled the moment while chatting to People magazine. She said, “He was waiting on our old wicker love seat, ring in hand, with the most beautiful proposal any best friend could ever give.” The pair married at a Lake Tahoe ceremony that same year.

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And true to their beliefs, the pair staged a somewhat untraditional event. For one thing, the eco-friendly couple used recycled invitations, old bamboo chairs and abandoned barrels to create their own bar. Their officiant also blessed them with water that he’d personally collected from the lake. The whole thing then finished with the pair and their loved ones eating vegan burgers and singing Beatles tunes around a fire.

And six years later, the pair became parents when Silverstone gave birth to son Bear Blu. In 2012, though, the actress once again courted controversy when she uploaded a video clip in which she gave her son food she’d first chewed herself. Yet despite concerns that she could have passed on viruses and bacteria to her little one, Silverstone later said she had no regrets about the practice.

Her seemingly happy family life wasn’t set to last, however. After nearly two decades together, you see, Silverstone and Jarecki decided to separate in 2016. Yet the pair initially kept their split secret from the media. In fact, they only publicly confirmed that they had parted ways in a February 2018 statement.

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A representative for the pair told Page Six, “They still deeply love and respect each other and remain very close friends but have mutually decided to separate after being together for 20 years. They have a son together who they will continue to co-parent.” Shortly after this, Silverstone officially filed for divorce.

Yet in a subsequent interview with Working Mother, Silverstone admitted that she was open to the idea of having another child with Jarecki in the future. She said, “I’ve always wanted another kid. But I also wanted to space them out because I love being with Bear. They’re too delicious to have another one come along.”

Silverstone continued, “When Bear was three and a half, I started to feel like I was ready to have another baby. But it wasn’t the right time in my life, so I waited. I have always dreamed of having a little girl, but of course I want another little Bear too. I’m not in a relationship, but there are other ways to make babies.”

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Silverstone also discussed the separation in an interview with Redbook. In July 2018 the star told the magazine, “Obviously, it’s heartbreaking. You don’t ever think you’ll be apart when you get married. All I can really say is that we’ll co-parent Bear together, and this is completely a good thing for both of us.”

Silverstone then revealed in the same interview that she’d already started to hit the dating scene. She said, “I find it very fascinating meeting interesting, intelligent, different people. I’m super excited about being available and open to whatever’s next. Of course, there’s tons about it that’s confusing. I call my girlfriends, and I’m like, ‘What does this mean?’”

But in the Working Mother interview, Silverstone revealed that she hadn’t yet spoken to Bear Blu about her new dating life. She said, “He doesn’t have any idea that I’ve ever been on a date. I have talked to him about how one day mommy and daddy might want to find another person to be with. That was hard.”

Silverstone continued, “We had a really deep conversation about it, where I was preparing him in case I did find a boyfriend. But I just wanted to check in on him to see how he was doing. I would say, ‘Mommy and daddy like to live separately.’”

In the end, Silverstone and Jarecki finalized their divorce in November 2018. This was after the pair had hired a private judge to assist them with various issues that they’d had trouble settling themselves. And it was one particular aspect of the settlement that made headlines when it was revealed to the press.

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Entertainment Tonight in fact reported that official court documents stated that Silverstone had to pay $12,000 each month to her ex-husband. And she seemingly also has to dish out this costly spousal support on the first of the month until early 2024. It seems, though, that the agreement did come with some stipulations.

And if this is true, Jarecki would certainly have to think twice about co-habiting with a new love for a long period of time. The documents supposedly state, after all, that if the rocker decides to share his living space with a “romantic partner” for more than five months in a 12-month period, he will immediately forfeit all of his financial support. And that’s not all.

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Jarecki could also reportedly lose his tidy monthly sum if he moves in with anyone unrelated. Supposedly, you see, another stipulation involves a housemate financially contributing to at least half of the housing costs for five months in a 12-month period. So if this occurs, Silverstone will apparently be well within her rights to stop the payments.

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Yet as well as settling the financial aspects of their divorce, the pair also managed to agree to a custody arrangement. It seems that Silverstone and Jarecki will both be responsible for bringing up son Bear Blu in equal measure. An exact schedule was even agreed at a later date.

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So the couple’s divorce was made official in December 2018. This was ten months after the pair had first revealed their split to the public and more than two and a half years after they had actually separated behind closed doors. Irreconcilable differences were cited as the official cause of separation.

Of course, Silverstone isn’t the first celebrity to make very specific requirements in a divorce settlement. Following Katie Holmes’ split from Tom Cruise, for instance, Holmes reportedly demanded an “ironclad” clause to prevent her daughter, Suri, from becoming too involved with Scientology. It apparently even stated that her ex-husband mustn’t take the child to any of the organization’s meetings or churches.

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And Cruise also reportedly insisted on a watertight clause himself. This apparently stated that Holmes wasn’t allowed to discuss her marriage to the A-lister or publicly hit the dating scene for at least five years. And the former Dawson’s Creek actress supposedly bagged millions of dollars for both herself and her child after sticking to the clause.

Chris Pratt and Anna Faris also agreed on a specific clause involving their children following their divorce. In fact, official court documents reportedly showed that they both insisted that neither party could live more than five miles away from the other until their son, Jack, has finished sixth grade. Each parent also apparently has to give at least a month’s warning if they want to travel abroad with their son.

Pratt told Entertainment Weekly, “Divorce sucks. But at the end of the day, we’ve got a great kid who’s got two parents who love him very much. And we’re finding a way to navigate this while still remaining friends and still being kind to one another. It’s not ideal, but yeah, I think both of us are actually probably doing better.”

And then there’s the case of Andrew and Lauren Silverman. The latter became a tabloid regular in 2013 when it was revealed that she was pregnant with Simon Cowell’s child. So in the Silvermans’ divorce settlement, Andrew apparently insisted that the music mogul must keep his distance from their own son, Adam, for two years.

The divorce apparently also stated that Lauren would have had to fork out approximately $45,000 if she’d broken the rule. Adam further isn’t supposedly allowed to call anyone other than his biological parents mom and dad. In return, Andrew reportedly agreed not to slate Cowell or allow anyone in Adam’s company to make disparaging remarks about The X Factor judge.

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But none of that makes divorce any easier for Silverstone and Jarecki. In fact, Silverstone has seemingly spent much of her time since the split working. She appeared alongside screen legends Jane Fonda and Diane Keaton in the 2018 movie Book Club, for instance. The star will then join the likes of Riley Keough and Richard Armitage in 2019 horror film The Lodge.

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Silverstone will also star as a woman who tries to prevent the marriage between her younger brother and his French girlfriend in 2019’s The Pleasure Your Presence. The actress also executive produced this Amy Miller Gross-directed drama. She will then continue her prolific streak with the big-screen comedy Judy Small.

In December 2018 Silverstone also posed nude for a PETA billboard advertisement placed in Times Square. The actress decided to go bare as a way of highlighting cruel practices in the wool industry. The ad actually remained in place when the famous ball dropped on New Year’s Eve.

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For his part, Jarecki hasn’t appeared on screen since he made a cameo alongside Silverstone in 2012’s Vamps. Instead, he now focuses his efforts on a radio show titled A Musical Journey with Christopher Jarecki. The GFTU show sees the star invite various guests to reflect upon five songs that have shaped their musical lives.