During his heyday, Robert De Niro was described as being handsome, mysterious, alluring, and a complete womanizer. Despite growing up during an era when interracial relationships weren’t widely accepted, Robert pursued, chased down, and broke the hearts of several women of color. This is a story about infidelity, a terminated pregnancy, a court battle over a secret love child, and a domestic situation that ended with some fractured ribs.
Here’s what we know about Robert De Niro’s super messy love life.
Jealous and possessive
Born in Manhattan on August 17, 1943, Robert Anthony De Niro Jr. dropped out of high school a few credits shy of earning his diploma. According to the Los Angeles Times, his mom pushed him to continue his education, but Robert had his heart set on becoming an actor.
During the ‘60s, he put all his focus on acting…and women. A book entitled De Niro: A Life by author Shawn Levy claims Robert would pursue women everywhere he went. Film producer Jonathan Taplin stated, “He picked these incredibly strong girls. He’d fight with them all the time. They would always be in tears the next morning and he would buy them some perfume.”
It was also noted that his insecurities would ruin his romances. The author wrote that if Robert believed his girlfriend was getting too much attention from another man, he would unleash his jealous and possessive side.
How Robert De Niro met Diahnne Abbott
Robert appeared in off-Broadway plays, theater shows, commercials, and low-budget films for the first few years of his career, before teaming up with director Martin Scorsese to star in Mean Streets. Three years later, while on the set of the film Taxi Driver, he met and fell in love with actress Diahnne Abbott. They were married in 1976, and Diahnne gave birth to their son, Raphael De Niro. Robert also adopted Diahnne’s daughter Drena from a previous relationship. It seemed like the playboy was ready to settle down, but that wasn’t the case…
In author Shawn Levy’s book, it was revealed that Robert was involved with other women throughout his marriage. Robert also spent a lot of time partying with his friends, the late actor John Belushi and Martin Scorsese. Sources stated that Diahnne spent most of her time in their marital home, while Robert split his time between New York and California. When he was at home with Diahnne, things were awkward. In 1977, the De Niros invited the New York Times into their home in Bel Air for a dinner party. The journalist noted that Diahnne was a statuesque beauty. She was also described as being a lovely hostess who prepared a buffet-style dinner for everyone. Robert reportedly sat in silence for most of the night — a mere onlooker in his own house. A close friend told the newspaper, “Bob is very Italian with Diahnne, very possessive and jealous.”
Kathi McGinnis, Robert’s New York, New York co-star, added, “I think he’s hiding something he thinks may be too weird. I mean he’s protecting himself with all that silence. There’s some part of him he can’t show because he’s afraid it’s insane.”
A writer for Playboy magazine was even more perplexed by Robert’s behavior. The interviewer noticed the actor gave a limp handshake and would seldom make eye contact. The writer added, “Ask him about his childhood, his parents, his interracial marriage and he’s ducking out the door.”
Robert De Niro’s love life gets messy
An article entitled, “Robert De Niro’s Super Messy Love Life” wouldn’t be complete with a full-blown affair, right? Well, in the ‘80s, Robert was driving his convertible in Los Angeles when he saw a beautiful woman in the car next to him. Her name was Helena Springs, an aspiring singer. Helena said, “I’d go fast, he’d go fast. I’d slow down, he’d slow down. This a*****e kept following me. I didn’t even know him.”
Finally, Robert put his hands in a praying position and said, “Pull over.” So Helena stopped, and he invited her to lunch. According to author Shawn Levy’s book, they went out to eat, and — despite Robert being a married man — he and Helena hooked up that same day. They engaged in a non-exclusive relationship, which resulted in Helena becoming pregnant. She reportedly terminated the pregnancy without notifying Robert.
She became pregnant a second time in late 1981. This time, she decided to keep the baby. When she told Robert about her plans, he reportedly flew into a rage. Helena claimed the actor began to verbally and physically intimidate her in an attempt to pressure her to terminate the pregnancy, but Helena went on to give birth to a baby girl named Nina on July 1, 1982.
Robert reportedly gave her $50,000 to help with the baby and even assisted her in setting up the nursery. But Helena said he refused to provide her with his medical history or a blood sample, in fear that Helena would use the information to try and obtain more money from him. Helena said she didn’t pursue any further financial assistance from Robert, and she added, “Black women are used to being courted by handsome, famous, rich white guys. So they don’t say no to whatever the man wants.”
How Robert De Niro met Grace Hightower
Things between Robert and his wife Diahnne were still chugging along. They even appeared in a few more movies together. But in 1987, he became fixated on someone else.
During a visit to Mr Chow restaurant in London, he met a hostess and Mississippi native Grace Hightower. In an interview with the New York Times, Grace was apprehensive about giving too many details about their first encounter…possibly because Robert was still married at the time. She simply stated, “It was an ease-in. It wasn’t a whirlwind.”
Grace told the New York Daily News she had no clue who he was and was getting frustrated because he kept asking her so many questions about the restaurant’s tables and the menus. After complaining to one of her co-workers about the annoying patron, the co-worker told her the annoying customer was a very famous actor. This changed things for Grace, and it’s assumed they exchanged their contact information to keep in touch.
What happened between Robert De Niro & Whitney Houston?
Robert and Diahnne separated sometime around 1987, but it wasn’t necessarily his infidelity that caused their breakup. A source close to the former couple told Vanity Fair Diahnne wanted to live the celebrity lifestyle in the spotlight and Robert didn’t. Their differences caused too many issues in their relationship.
They remained legally married, but Robert was ready to see what else was out there. His London boo Grace was still in the picture, and there were rumors he had his eyes on another woman. In the book De Niro: A Biography written by John Baxter, it was revealed that Robert aggressively pursued Whitney Houston by sending her flowers and diamond earrings. According to the author, Whitney’s parents and record executive Clive Davis urged her to ignore Robert’s advances because they believed it would ruin her career if she was linked to a white man who’s almost twice her age.
Falling for Toukie Smith & Naomi Campbell
Robert may have been snubbed by Whitney, but he had a bunch of other women who were willing to give him a chance. He began dating actress Toukie Smith while he was still legally married to Diahnne. He and Toukie dated for many years and eventually welcomed twin boys Aaron and Julian via surrogate. in 1995. Despite being close companions, Vanity Fair revealed they never lived together under the same roof.
News outlets reported Robert had flings with supermodels Veronica Webb and Naomi Campbell, who was just 21 at the time. Naomi even reportedly declared that 48-year-old Robert was her man during an interview. When the New York Times questioned Toukie about Robert and Naomi’s relationship, Toukie insisted she preferred to keep everything pertaining to her personal life private.
Helena’s return
And what did Robert think about getting caught up in a love triangle? Well, he had other things to worry about. In August 1992, his ex-lover Helena Springs popped back into the mix. By this point, she was married, going by the name Helena Lisandrello, and she wanted Robert to pay child support for her daughter, who was then ten years old.
Robert finally agreed to submit a blood test, and the results concluded he was not the biological father. Helena clapped back by telling the court Robert still owed her money because he told her daughter that he was her father. The court wasn’t buying it and Robert cut off all financial assistance after the paternity test results were revealed.
Linking back up with Grace Hightower
The Baltimore Sun reported his relationships with both Toukie and Naomi fizzled out in the mid-‘90s, and Robert was back on the market…kind of. There was another woman who had been waiting in the wings for several years — the hostess from Mr. Chow restaurant, Grace Hightower.
He and Grace were married in 1997 and welcomed their son Elliot De Niro in 1998, who was later diagnosed with Autism. And in August 1999, Robert filed for divorce. A source told People magazine they split because Robert wasn’t making their marriage a priority, but divorce documents told a different story.
After quietly co-parenting their son for more than a year, a custody battle erupted. Robert accused Grace of having a bad temper and claimed she fractured his ribs during an argument. He also accused her of punching him after she saw him talking to a female chef during a family vacation on a yacht. Grace responded by saying she actually walked in on Robert getting frisky with the chef in one of the yacht’s restrooms. She claimed the actor was a heavy drinker and was using substances, which Robert denied.
A Manhattan court judge recommended they both visit a psychiatrist to discuss their issues in further detail. Despite all the mudslinging and accusations, they called off the divorced and renewed their vows in 2004 during a ceremony in upstate New York.
In December 2011, 67-year-old Robert and 56-year-old Grace welcomed their second child, a baby girl named Helen, who was conceived via surrogate. Robert was officially the father of six children by three different women.
Did money issues come in between Robert De Niro & Grace Hightower?
Things finally began to settle down for the De Niro family. Robert continued his acting career while Grace launched a coffee company called Coffee of Grace — a humanitarian-based business inspired by the people of Rwanda. But it was the coffee company that reportedly caused tension between the couple. Robert was reportedly concerned about how expensive the new venture was. In 2017, a source told Page Six they overheard Robert telling Grace at a Manhattan bar, “I wouldn’t have to keep making movies if you didn’t spend all my money!”
On November 20, 2018, a source told Page Six Robert and Grace were not living together. Eight days later, 75-year-old Robert announced in a statement that their marriage was entering a period of transition.
His friends were reportedly pleased that the actor was putting himself out of his misery. An insider told Radar Online Grace had made his life miserable for years by controlling his finances and his film production company. The source added, “Grace micromanaged him to death and he deserves a medal for sticking it out so long.”
By February 2020, they had signed off on a 31-page custody agreement for their daughter. But as far as a divorce settlement, things weren’t going to be that easy. There was a prenup in place, which stated Grace was entitled to a $6 million apartment, $500,000 in cash, $1 million per year in alimony, and half the value of their marital residence. But in divorce documents, Grace claimed to only earn $15,000 a year, so she thought she should be entitled to more of Robert’s $500 million fortune.
Robert De Niro & Grace Hightower’s messy divorce battle
Almost three years after filing for divorce, they continued to battle it out. In April 2021, Robert said he was working himself to death in order to keep financing his estranged wife’s lavish lifestyle. He told the court Grace was blowing money purchasing expensive jewelry and designer goods by Stella McCartney.
Grace’s lawyers claimed Robert had cut the amount of money he was giving per month, from $375,000 to just $100,000. He also cut her credit card limit from $100,000 to $50,000 per month. His lawyers argued the coronavirus pandemic had decimated his finances, plus he owes $6.4 million in back taxes. His lawyers say that at the age of 77, Robert should be able to relax and enjoy his life. But instead, he’s forced to work six days per week, 12 hours per day to continue paying for Grace’s lifestyle.
Grace’s lawyers were not buying it. They said there was no way Robert was struggling while flying to brunch in a helicopter every Sunday and meeting up with friends in Florida by traveling in a private jet.
As of this article, they continue to hammer out the final details of the divorce settlement, and we wish them and their family nothing but the best. Let us know your thoughts on Robert De Niro’s super messy love life or leave us a comment on our YouTube channel!