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Donald Trump's daughter Tiffany is dating a Democrat who likes Hillary Clinton

• Ross Mechanic, 21, is currently dating Tiffany Trump, 22, daughter of the GOP Presidential hopeful
• They are both students at the University of Pennsylvania; he is studying software engineering, she's a sociology and urban studies major
• Daily Mail Online investigation can reveal the young couple are connected by their roles as heirs to ultra-wealthy, New York real estate dynasties
• 'To the greatest real estate lawyer in the world, best wishes, Donald,' the inscription Trump wrote in book given to Ross's father, Jonathan Mechanic
• Mechanic's social media accounts portray an elite world filled with white-table cloth brunches, glitzy nights out at NYC clubs, attending the US Open

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.

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.