EXCLUSIVE: Donald Trump's daughter Tiffany is dating a Democrat who likes Hillary Clinton and lives in $2M NYC apartment owned by his mega rich real estate lawyer father who has known the GOP candidate for years

For the boyfriend of Tiffany Trump, meeting his girlfriend's father for the first time might be an occasion more awkward than most such encounters. Try explaining to the fiery Republican frontrunner that you are a registered Democrat with a liking for Hillary Clinton.

Ross Mechanic, a 21-year-old software engineering student, was pictured on Friday night up close and personal with Trump's daughter Tiffany, 22, at the glitzy Winter Wonderland Ball in New York's Botanical Garden. 

In a photo posted to her Instagram account, Tiffany was seen in a sparkly, gold strapless gown with a thigh-high split, paired with half-sister Ivanka's drop earrings, diamond bracelet, and cocktail ring. Alongside her was Ross, looking dapper in a tuxedo.

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New couple: Ross Mechanic and Tiffany Trump met while attending the University of Pennsylvania. They have been linked over the past five weeks

All that glitters: Tiffany also posed solo inside at the Winter Wonderland Ball in New York's Botanical Garden posting this photo to Instagram with the caption 'It's beginning to look a lot like Christmas'

Living large: Like Tiffany, Mechanic's social media accounts portray an elite world filled with white-table cloth brunches, glitzy nights out on the New York club scene, attending the U.S. Open and pool parties

Left leaning: The 21-year-old tech student is a registered Democrat with a liking for Hillary Clinton, who could likely be Donald Trump's opponent in the 2016 Presidential election if both are their parties nominees

Judging by Ross's social media accounts, it looks as though he and Tiffany have been dating for weeks. 

One of his Instagram pictures shows the couple on a night out at the Fire & Ice Lounge in Philadelphia five weeks ago.

It might be that Ross met Tiffany at college - both are students at the University of Pennsylvania; where he is studying software engineering and she is double majoring in sociology and urban studies.

But a Daily Mail Online investigation can reveal that the young couple are connected by their roles as heirs to ultra-wealthy, New York real estate dynasties and that their powerful fathers have known each other in the business world for at least a decade.

Billionaire Trump even once signed a copy of his book, The Art of the Deal, for Ross's father, real estate lawyer Jonathan Mechanic, with the inscription: 'To the greatest real estate lawyer in the world, best wishes, Donald.' 

When reached by phone for comment on her son’s new relationship, Wendy Sue Levine said ‘not interested’ and hung up. No other family members responded to emails or messages.

The Mechanic family – Jonathan, 63, his wife Wendy Sue Levine, 59, and sons Marc, 25, and Ross, 21 – are all registered, active Democrats, according to public records. Both Jonathan and Wendy Sue have been registered Democrats since 1988.

Ladies man: Ross Mechanic's social media accounts show him getting cozy with several other beauties

Party time: Mechanic sips on a drink and switches from blondes to  two brunettes

Best education: Ross graduated in 2013 from Friends Seminary, a private Manhattan day school where annual tuition currently costs $39,800, according to the website

Among Ross' Facebook 'likes' are Hillary Clinton and he also appears to support such liberal causes as Naral Pro-Choice NYC – a non-profit aiding safe and legal abortions for women from all backgrounds - and the Penn Green Campus Partnership for environmental sustainability and policy development, according to his social media.

Tiffany, who is Donald Trump's only child from his five-year marriage to Marla Maples, recently spoke in support of his political campaign on 20/20, telling Barbara Walters: 'He's true to himself. 

'And he speaks in a way that the average person can understand. I think that's refreshing for everyone.

'I'm so happy to be Tiffany Trump, happy to be in the family I'm in,' Tiffany shared.

She has been seen on the sidelines of Republican presidential debates, supporting her dad, 69, with her elder siblings – Donald Jr., Eric and Ivanka - and Donald's third wife Melania, with whom he had his fifth child, Barron, in 2006.

But while Ross perhaps does not align with his girlfriend and her father politically, the 21-year-old does appear to have a head for business.

He is due to graduate in 2017 from Penn with a BSE in Computer Science, according to his LinkedIn profile, and has a 'limited working proficiency' of Arabic.

The 21-year-old spent the summer in the tech hub of San Francisco interning at Idibon – a company which provides state-of-the-art language processing services.

Like his new girlfriend Tiffany, who was first seen in 2014 amid the Rich Kids Of Instagram, Ross also appears to have a penchant for the party circuit.

In 2014, he had a four-month summer internship with the AIM Hospitality Group, supervising a promotions team for events in New York City and the Hamptons. AIM is behind glitzy events at some of Manhattan's most exclusive clubs including Up & Down, the High Line Ballroom, Lavo and the Dream Hotel.

Like Tiffany, his social media accounts portray an elite world filled with white-table cloth brunches, glitzy nights out on the New York club scene, attending the U.S. Open and pool parties.

Ross graduated in 2013 from Friends Seminary, a private Manhattan day school where annual tuition currently costs $39,800, according to the website.

High profile: Jonathan Mechanic, 63, is a partner and chairman of the real estate department at international law firm Fried, Frank, Harris, Shriver and Jacobson, he has been involved in some of the city's preeminent property transactions including the World Trade Center, Hudson Yards on the West Side, Brooklyn's Atlantic Yards and the new downtown Whitney Museum

Party affiliation: Jonathan Mechanic and Wendy Sue Levine have been registered Democrats since 1988, both of their sons - Marc and Ross - are as well

Buds: 'Happy 25th birthday to the best brother out there,' wrote Ross to his brother Marc, 25, on Instagram

Notable alumni include President Theodore Roosevelt, the actors Liev Schreiber, Amanda Peet and Kyra Sedgewick, and designer Vera Wang.

His lengthy school achievements include becoming a National AP Scholar, National Merit Finalist and president of the debate team.

He volunteered with third grade students during high school through non-profit, Go Project, and in his freshman year at college tutored local elementary school students in math each week.

When not attending Penn, Ross lives in a luxury apartment, owned by his parents, in a 19th-century co-op building in downtown Manhattan.

Apartments in the building have recently sold for around the $2 million mark, according to Zillow and Streeteasy.

Ross' father has been a powerhouse of the New York real estate world for almost four decades.

As partner and chairman of the real estate department at international law firm Fried, Frank, Harris, Shriver and Jacobson, he has been involved in some of the city's preeminent property transactions including the World Trade Center, Hudson Yards on the West Side, Brooklyn's Atlantic Yards and the new downtown Whitney Museum.

He also teaches a course in real estate law at Harvard Law School and lectures at New York University.

In a 2004 list of New York's Top Real Estate Lawyers, it was noted that Jonathan 'is a man who does not suffer fools gladly'.

This year, he was included in the Commercial Observer's 'Power 100' list at number 76 (the only practicing lawyer to make the cut). Donald Trump was at number 13.

In August, Jonathan spoke to Reuters about Donald Trump, describing a summer's day in 2005 when the billionaire gave him a tour of vacant real estate space at Trump Tower on Fifth Avenue. 

Supporting dad: 'I'm so happy to be Tiffany Trump, happy to be in the family I'm in,' Tiffany told 20/20. She has been seen on the sidelines of Republican presidential debates, supporting her dad

Say cheese: Tiffany and Ross (top left) smile for the camera at what appears to be an event at Penn as she and another friend strike a pose together

Cozied up: Ross Mechanic was pictured on Friday night with Tiffany at the glitzy Winter Wonderland Ball in New York's Botanical Garden

Jonathan, acting as counsel for Gucci, said the high-end brand already wanted to move into the building but that Trump still gave him the hard sell, in his characteristic style.

The lawyer told Reuters that Trump said 'it was the best retail space, in the best retail building, on the best corner, in the best city in the world'. 

In a 2009 interview with the New York Times during the US recession, the senior Mechanic said that business was booming at his law firm: 'I think the mood is clearly up – we noticed it at our holiday party. It was at Cipriani 1,000 people showed up.' 

Jonathan has received a number of awards for philanthropy including a humanitarian award from the Real Estate Board of New York.

He has also been honored for his charitable efforts at a long list of organizations including the National Jewish Hospital, Albert Einstein Medical College, the Police Athletic League and the Modell Foundation.

He also revealed to the New York Times that he invested in real estate and owned retail and office space in Bergen County, New Jersey which he managed with his wife Wendy Sue.

Jonathan Mechanic and Wendy Sue Levine married at the Park Lane Hotel in New York City in early November 1987, the year that he made partner at Fried Frank.

According to their New York Times wedding announcement, Levine's parents, Dr. Frank Levine, a dentist, and his wife, Jane, came from New Jersey. 

Jonathan Mechanic's parents were noted as Dr. Mayer Mechanic, also a dentist, and his wife, Bernadine Mechanic, CEO of Allendale Automotive Enterprises in Ho-Ho-Kus, New Jersey.

The wedding was officiated by Rabbi David Panitz and son, Rabbi Michael Panitz, of Palm Beach, Florida, according to the Times.

The article noted that the 'bride will retain her name', and that Levine worked as a senior account manager at Product Movers, publishers of newspaper inserts. 

She graduated from George Washington University in DC before receiving an MBA at NYU.

Jonathan is noted as a graduate magna cum laude from Brandeis University in Massachusetts and received his law degree from the NYU School of Law.

In 2010, the couple were significant donors in the 'Dean's Alumni Circle' to NYU.

The couple own an oceanfront property in the exclusive enclave of East Hampton, New York. Zillow estimates that the property is worth around $3 million. 

Ross has an older brother, Marc Mechanic, who followed in his father's footsteps into real estate litigation and works for Meadow Partners in New York City.