After dating for ten years, Robert De Niro finally tied the knot with the woman who would become his second wife. Even though De Niro and his wife got back together after he filed for divorce, their marriage ultimately did not survive the ordeal. Instead, it resulted in a contentious divorce case for both parties.

At a nightclub in London in 1987, renowned actor Robert De Niro had his first encounter with the woman who would later become his wife, Grace Hightower. However, the first sparks did not flare until 10 years after the first meeting.

When they met paths, De Niro was still married to his first wife, Diahnne Abbott, whom he had wed in 1976. This was at the time that they came into contact with one another. In the course of their marriage, the couple became parents to two people: a girl who they named Drena and a boy who they named Raphael. In 1988, Abbott and De Niro finalized their divorce.

After dating a few other women in the aftermath of his divorce, De Niro pursued Hightower, and the two soon developed a blossoming relationship. In June of 1997, the happy couple exchanged vows in front of family and friends at their home in Marbletown, New York.

There were just eleven people present as the couple said their wedding vows at the private ceremony, and two of the producer’s friends, Joe Pesci and Harvey Keitel, were there to witness the event. In the autumn of the same year, it became public knowledge that the wedding couple was expecting their first child together. In March of 1998, they welcomed a son named Elliot into the world.

In March of 2016, Robert De Niro disclosed that his kid has been diagnosed with autism. In a statement to the media, he mentioned how important it was to discuss topics related to society in an open manner:

“Grace and I are the parents of a kid who has autism, and we feel strongly that all of the problems surrounding the potential origins of autism should be explored and publicly addressed,”

In August of 1999, the two-time Academy Award winner filed for divorce from his wife, Hightower, exactly one year after the birth of their son. After then, one of his close friends revealed that he had been neglecting his marriage:

“Bobby wasn’t putting in nearly enough effort to make his marriage to Grace work,” Grace said.

The former couple went their own ways and proceeded to have happy, successful lives. They shared parental responsibilities for their child and behaved like a unified family unit while they were with him. On the other hand, it lasted for barely a year.

On the vacation that the trio took in June of 2001 with their kid Elliot, they were joined by the artist Marc Anthony, his then-wife Dayanara Torres, and their son. The trip was marred by conflict as a result of the trio’s presence. When Hightower went belowdecks, she found her husband with another woman, at which point they had been separated.

After some time had passed, a reliable source revealed that the mystery lady had only been helping Robert De Niro by shutting the door to the restroom. Hightower, on the other hand, was certain that there was more to the story.

She attempted to embarrass him by walking back up to declare what she had seen, which, according to her publicist, R Couri Hay, was De Niro’s “frozen expression on his face” and the lady who purportedly looked to pull her “blouse closed.” She was unsuccessful in her attempt to disgrace him.

After Hightower appeared, De Niro pursued her, and she immediately began to engage in physical contact with him. After some time, she got off the boat with their child.

According to People, in September 2001, the on-again, the off-again couple faced off against each other in the New York State supreme court in a custody dispute for their kid. The charges of violence and alcohol abuse that were brought up throughout the proceeding were as follows:

Additionally, De Niro said that the former flight attendant had harmed him physically. In his response to the petition, Hightower said that the native New Yorker had a problem with substance abuse and alcoholism, and he indicated that it was probably not a smart idea to leave him alone with their child. As a result, she made a strong effort to prevent him from having unsupervised contact with Elliot after he filed the petition.

In a perverse twist of circumstances, the couple made the decision to call off the divorce proceedings. After that, in November of 2004, Hightower and the Golden Globe Award winner decided to recommit themselves to one another in marriage.

The wedding took place on De Niro’s estate in Ulster County, and visitors included a number of A-list actors and actresses from Hollywood, such as Meryl Streep and Ben Stiller, amongst others.

The star-studded event was presided over by two judges at the actor Robert De Niro’s request. The actor who played Michael Corleone in “The Godfather” said that the actor’s goal was to guarantee that “they can make sure this one stays.”

The ceremony took place all around a swimming pool, and during it, the bride and groom exchanged wedding rings and lighted candles. After that, the guests walked inside a tent, where they drank champagne and feasted on meals from De Niro’s restaurant, Nobu.

In 2011, the couple received their second child and only daughter, Helen, who was carried by a surrogate. This event brought the pair even more joyous news. In an interview with CBS News in 2013, De Niro raved over his daughter in the following way:

“She is so cute it hurts. When you look at her, everything is right there in front of you. Nothing else matters.”

In spite of this, things proceeded from bad to worse throughout the years, culminating in his filing for divorce for the second time in November 2018, after having been married for almost twenty years.

In a statement announcing the split, De Niro said that, despite the fact that he and Hightower had “two lovely kids” together, they were going in separate directions with their lives:

“In terms of our connection, we are moving into a transitional phase, which is a process that is challenging but ultimately beneficial. As we continue to establish our roles as parenting partners, I want to acknowledge Grace as the beautiful mother that she is, and I ask that everyone give us some space and respect as we do so.”

In January of 2019, Page Six published an article claiming that the divorced couple was once again engaging in a covert court custody fight over their daughter, who was seven years old at the time.

They chose to have the case captioned with the desired phrase “Anonymous vs. Anonymous” because their goal was to shield their family from the back and forth that would take place in the courtroom. In accordance with the decision handed down by the court of appeals in 2006, this alternative should be used “judiciously” in order to safeguard the “health and welfare” of youngsters.

Because he is a wonderful and attentive father of two children, the “Goodfellas” actor’s first priority was to find a solution to the problem that included the children.

Additionally, in addition to the conflict about custody, the couple clashed in court on financial matters. During the course of their court battles, Hightower started spending an increasing amount of Robert De Niro’s money.

His attorney, Caroline Krauss, said that the philanthropist’s spending habits were out of control and that this had a significant impact on Robert De Niro’s fortune, which she estimates to be in the range of $500 million.

It is believed that Hightower spent a total of $1.67 million in 2019, with the majority of the funds going toward the acquisition of a diamond worth $1.2 million from exclusive New York jewelers.

As a consequence of her irresponsible use of financial resources, De Niro’s finances deteriorated, and he was compelled to toil away until the day he “passed away” in order to support her extravagant way of living. He is already quite close to reaching the age of 80.

According to Page Six, Krause said that Hightower has costly taste, which includes her “thirst for Stella McCartney” and diamond rings that cost over a million dollars. In the meanwhile, it has been alleged that her estranged spouse owes millions of dollars in back taxes. A study from 2015 states that De Niro has a debt of around $6.4 million.

At the same time, he does not want his family to uproot from the house that they have shared in Manhattan since their marriage. According to the prenuptial agreement, Hightower and Hightower should sell their $20 million condo so that they may divide the money and so that Hightower can buy a more affordable house for himself, Hightower, and their children.

In the meanwhile, Krause presented evidence in what amounted to a virtual divorce court, arguing that if Hightower expects De Niro to continue working till the end of his life, and if his health deteriorates to the point where he passes away, then Hightower’s spending binge would come to a stop:

If he were to get ill the next day, the celebration would be canceled.

To De Niro’s good fortune, he was able to stop Hightower from inheriting fifty percent of his riches. A ruling by an appeals court in October 2021 set the amount at $250 million.

In a prenuptial agreement from 2004, the actress asserted that she was entitled to half of the “Taxi Driver” star’s money while they were still married even though they had a prenuptial agreement. According to Hightower, De Niro’s assets were meant to be divided fairly amongst everyone.

However, she was unsuccessful since the Appellate Division issued a ruling that was contrary to her position and determined that the Hollywood veteran did not owe her anything:

The income made by the husband throughout the marriage, in addition to any other business assets obtained during that period, is considered to be his independent property.

A similar decision was rendered in February 2021 by a judge named Matthew Cooper of the Supreme Court of Manhattan. In his opinion, the judge stated that the former couple’s prenuptial agreement states that any money that De Niro made during their marriage from a variety of sources was considered to be part of his separate income.

According to the reports, Hightower’s monthly expenditures consisted of $215,000 on credit cards and $160,000 in cash. According to Krauss, De Niro’s spending habits caused him to exhaust his financial resources. The court did not buy her assertion that the money should be considered “marital assets” since the couple had previously agreed to treat it as such.

Despite the ups and downs of his relationship with Hightower, who is technically still his wife, Robert De Niro is able to maintain a healthy relationship with his daughter. The father and daughter were seen going about their business on the Upper East Side of New York City in the month of July 2022. According to the Daily Mail, it is not unusual for the two of them to be seen together when out and about in public. While this is going on, the star of “The Irishman” has apparently begun dating someone else. It has been said that he is seeing a woman by the name of Tiffany Chen, and the two of them have been seen together in public on many occasions. The aforementioned pair was seen on a beach vacation in Formentera, Spain, in the month of July 2022.

The two were seen in photographs going barefoot while on board a boat. Notably, De Niro and the martial arts teacher have been seen being affectionate in public, but neither party has come out to confirm nor deny that they are romantically involved with one another.