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Ivana Trump enjoys a lunch date with her on-again, off-again boyfriend Rossano Rubicondi in New York

Ivana Trump was spotted enjoying a lunch date with her ex-husband-turned-ex-boyfriend Rossano Rubicondi in New York City on Tuesday. 

The Czech-born socialite, 72, took advantage of the warmer weather and stepped out with the Italian reality star, 48, who dutifully carried her Yorkshire terrier, Tiger, while they strolled through the Upper East Side. 

The on-again, off-again couple spent an hour dining at French restaurant Match 65 Brasserie before heading back to her nearby townhouse with what looked like a bag of leftovers. 

History: Ivana Trump was spotted with her on-again, off-again boyfriend Rossano Rubicondi in New York City on Tuesday 

Lunch date: Ivana, 72, and Rossano, 48, spent an hour dining at French restaurant Match 65 Brasserie on the Upper East Sid

Lunch date: Ivana, 72, and Rossano, 48, spent an hour dining at French restaurant Match 65 Brasserie on the Upper East Sid

Ivana was dressed to impress in a satin trench coat and dress pants that matched the cherry red nail polish on her fingernails.  

Her platinum blonde hair was pulled back in her signature beehive with her bangs framing her perfectly made-up face. She sported thick black liner around her eyes and rosy-pink lipstick, her preferred beauty look in recent years.  

The businesswoman topped off the look with her beloved Lady Dior mini bag, which she carried in her right hand, and a pair of black flats.  

Ivana also had on two face masks, which she has rarely been seen wearing amid the COVID-19 pandemic. 

While she was a vision in red, Rossano opted for an all-black look that included a wool coat over a puffy vest, dress pants, and a matching face mask.

Ivana’s arm was wrapped around his for support as they navigated the busy city streets together with Tiger in tow. The dog was on a leash, but it appears as though he needed to be carried.  

Dolled up: Ivana's platinum blonde hair was pulled back in her signature beehive with her bangs framing her perfectly made-up face

Dolled up: Ivana’s platinum blonde hair was pulled back in her signature beehive with her bangs framing her perfectly made-up face

Outfit of the day: The socialite made a statement in a bright red satin trench coat

Outfit of the day: The socialite made a statement in a bright red satin trench coat 

Double masking: Ivana took extra precautions and had on not one but two face masks for their outing

Double masking: Ivana took extra precautions and had on not one but two face masks for their outing

Support: The Czech-born businesswoman held onto Rossano's arm as they walked

Support: The Czech-born businesswoman held onto Rossano’s arm as they walked 

Rossano had his hands full as he held onto Tiger and a brown bag that was likely filled with leftovers from their lunch. At one point, he was seen smoking a cigarette as they walked home together. 

The two have maintained that they are close friends, though Rossano has previously said that a romantic reunion is always possible.  

Ivana announced their split back in June 2019 before escaping to Saint-Tropez for the summer, admitting that the time she spends on the French Riviera was part of the reason why she and her longtime beau couldn’t make their relationship work.

‘The relationship just ran its course,’ she told Page Six. ‘Rossano spends a lot of time in Italy and I spent a lot of time in New York, Miami, and Saint-Tropez, and he has to work.’

‘The long-distance relationship really doesn’t work,’ she added. ‘We had a good time and are friends. The split was amicable.’

Rossano, meanwhile, asserted that he has ‘good respect’ for the businesswoman following their breakup, but he later made it clear that her children were a source of ire in their romance. 

In walking distance: The French restaurant was located close to Ivana's Upper East Side. townhouse

In walking distance: The French restaurant was located close to Ivana’s Upper East Side. townhouse 

Like family! The former couple was joined by Ivana's beloved Yorkshire terrier, Tiger

Like family! The former couple was joined by Ivana’s beloved Yorkshire terrier, Tiger

Added touches: Ivana accessorized her look with her Lady Dior mini bag, which she carried in her right hand, and a pair of black flats

Added touches: Ivana accessorized her look with her Lady Dior mini bag, which she carried in her right hand, and a pair of black flats

Monochromatic: Rossano opted for an all-black look that included a wool coat over a puffy vest, dress pants, and a matching face mask

Monochromatic: Rossano opted for an all-black look that included a wool coat over a puffy vest, dress pants, and a matching face mask

He emphasized that he wasn’t after the matriarch’s fortune and suggested that money was often something he quarreled with her children about.

The former couple dated for six years before they tied the knot in 2008 during a lavish $3 million ceremony at Mar-A-Lago, the Palm Beach estate owned by none other than Ivana’s second ex-husband, Donald Trump.

But just eight months after their Midsummer Night’s Dream-themed nuptials, Ivana and Rossano announced their upcoming divorce.

Ivana said she had actually filed for separation three months prior and blamed the split on her and Rossano’s different preferences for their cities of residence.

The couple had faced rumors that Rossano had been unfaithful to her while filming the TV show Survivor in Honduras, which Ivana denied in her Page Six column just a month before their split.

Rossano was Ivana’s fourth husband after Alfred Winklmayr, Donald, and Riccardo Mazzucchelli, but the two didn’t stay apart for long.

Beauty look: Ivana sported thick black liner around her eyes and rosy-pink lipstick, her preferred beauty look in recent years

Beauty look: Ivana sported thick black liner around her eyes and rosy-pink lipstick, her preferred beauty look in recent years

Letting him walk: Rossano, who was carrying both Tiger and what appeared to be their bag of leftovers, finally stopped to put the dog down

Letting him walk: Rossano, who was carrying both Tiger and what appeared to be their bag of leftovers, finally stopped to put the dog down

Something to see: A passerby couldn't help but stop and stare as they fussed with the dog

Something to see: A passerby couldn’t help but stop and stare as they fussed with the dog 

Here we go: Tiger led the way as they continued to walk home to Ivana's townhouse

Here we go: Tiger led the way as they continued to walk home to Ivana’s townhouse 

Looking back" The former couple dated for six years before they tied the knot in 2008, but just eight months later they announced their upcoming divorce

Looking back” The former couple dated for six years before they tied the knot in 2008, but just eight months later they announced their upcoming divorce

They reunited shortly after their divorce and spend a great deal of time together until Ivana announced nearly two years ago that she had broken up with him. 

However, they’ve never really stayed apart. They’ve been seen together numerous times since their most recent public split. 

A few weeks ago, Ivana received a visit from her daughter Ivanka Trump, who stopped by her townhouse to give her a belated gift after missing her birthday on February 20.  

Ivanka, who was only in New York for a couple of days, was seen taking a carefully wrapped present to her mother’s house, where she stayed for about an hour.

The former first daughter has been living in Miami, Florida, with her husband Jared Kushner and their three children.  

They’re living at the luxury apartment building Arte Surfside, one of the most expensive complexes in the neighborhood, with an average rental price of nearly $47,000 per month. 

It has been reported that the couple has leased the home for a year while they build a more permanent property on a plot of a two-acre plot of land that they purchased on Indian Creek Island — also known as the ‘Billionaire Bunker’ — for $31.8 million in late 2020.   

Ivana’s eldest child, Donald Trump Jr., is also understood to be living in Florida with his girlfriend Kimberly Guilfoyle, leaving only Eric Trump and his wife Lara in New York. 

What a pal: The two later reunited only to break up again, with Ivana publicly announcing their split back in June 2019, but they've both maintained that they're still friends

What a pal: The two later reunited only to break up again, with Ivana publicly announcing their split back in June 2019, but they’ve both maintained that they’re still friends

Can't stay apart: Ivana and Rossano been seen together numerous times since their most recent public split nearly two years ago

Can’t stay apart: Ivana and Rossano been seen together numerous times since their most recent public split nearly two years ago

Taking the edge off: Rossano was seen smoking a post-lunch cigarette while they walked to Ivana's home

Taking the edge off: Rossano was seen smoking a post-lunch cigarette while they walked to Ivana’s home 

The day before Ivanka’s visit, the mother of three went out to lunch with her youngest son Eric, 37, and her daughter-in-law Lara, 38. 

They ate the upscale Italian eatery Altesi Ristorante, one of Ivana’s favorite restaurants on the Upper East Side, before walking her back to her townhouse.

Eric was the only one who wore a mask when they left the restaurant, with his mother, his wife, and one of their Secret Service agents opting to forgo the protective face covering while strolling through the crowded city streets. 

Ivana was dressed to the nines in a flashy blue fur coat, which she wore over a black pantsuit. She topped off the look with a large, silver ball necklace that matched the zipper details on her blazer and black flats.  

Lara was dressed a bit more casually in a blue ribbed top, cropped skinny jeans with a frayed hem, and Golden Goose’s intentionally distressed shearling sneakers, which retail for an eye-watering $630. 

The mother of two kept warm in a lilac wool coat and carried a black leather handbag while strolling down the sidewalk with her husband and mother-in-law.

Lara wore black-framed sunglasses and her large gold hoop earring peeked out from underneath her long blonde hair when it blue in the wind. 

Catching up: A few weeks ago, Ivana received a visit from her daughter Ivanka Trump, who stopped by her townhouse to give her a belated gift after missing her birthday on February 20

Catching up: A few weeks ago, Ivana received a visit from her daughter Ivanka Trump, who stopped by her townhouse to give her a belated gift after missing her birthday on February 20

Catching up: The 39-year-old stopped by her mother Ivana Trumps Upper East Side townhouse with a belated birthday gift

Presentation: Ivanka, who was only in New York for a couple of days, was seen taking a carefully wrapped present to her mother’s house, where she stayed for about an hour. 

City life: The day before Ivanka's visit, the mother of three went out to lunch with her youngest son Eric, 37, and her daughter-in-law Lara, 38

City life: The day before Ivanka’s visit, the mother of three went out to lunch with her youngest son Eric, 37, and her daughter-in-law Lara, 38

Almost in: Lara watched as Ivana got the keys out of her beloved Lady Dior bag when they dropped her off at her townhouse after lunch

Almost in: Lara watched as Ivana got the keys out of her beloved Lady Dior bag when they dropped her off at her townhouse after lunch 

Eric, meanwhile, sported a navy half-zip sweater over a crisp white button-down. Instead of a winter coat, he had on a blazer that matched his navy dress pants. 

Ivana held onto her son’s arm as they walked together, while he carried a paper bag that likely contained her leftovers from their lunch date. 

Eric and Lara said a short goodbye to his mother before they walked back to their home in Trump Tower, where their children Luke, three, and Carolina, one, were likely waiting.  

What is in store for the couple remains unknown; unlike the other Trump siblings, they are not believed to be relocating to the Sunshine State.

The couple has long been based in New York City, where they currently live with their two kids, but it is unclear whether they are planning to try and return to Manhattan life full time.

Many believed Ivanka and Jared would no longer be welcome in the same elite Manhattan social circles they once ran in before her father became president, which was thought to be one of the reasons for their move.  

However, Eric and Lara maintained a far more low-key profile while living in the city. They did not relocate to Washington, D.C. as Ivanka and Jared did early on in Trump’s presidency, which may give them a better chance to adjust. 


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