Who Is Tiffany Trump's Ex-Boyfriend?

Tiffany Trump is the only child of President Donald Trump and his second wife, Marla Maples. Born in 1993, Tiffany stayed out of the limelight and away from the publicity that shadowed her half-siblings by growing up in California with Maples. Referred to as "The Other Trump" by The New York Times, she kept a rather low profile until her father's presidential campaign, when she gave a speech at the Republican National Convention. 

Before that, Tiffany was associated with the Snap Pack, a group of young, super wealthy, Instagrammable New Yorkers with famous parents. Now a graduate from the University of Pennsylvania, she's attracting more attention, which means everyone wants to know who she's dating. The answer, until recently, was college sweetheart Ross Mechanic. Alas, these two have reportedly gone their separate ways, but something tells us you haven't heard the last from this high-profile ex-boyfriend. Here's everything you need to know about him.

Go Quakers!

Ross Mechanic graduated from Tiffany Trump's alma mater, the University of Pennsylvania, in the spring 2017, one year behind his famous ex. As a a computer science major, he worked on a number of apps, including SpeakEasy, which gives bar and restaurant goers a glimpse at the establishment they're about to enter; and the Penn Spiral Surgery App, which allows patients to communicate directly with medical professional about their recovery. He also put his knowledge to use at work as a partner in the venture capitalist firm, Rough Draft Ventures, which assists undergraduates in beginning their own start-up companies.

Bipartisan bliss

Ross Mechanic, his parents, and his brother are registered as Democrats, which probably made for some awkward family dinners during the roughly two years that he dated Tiffany Trump. (They were first spotted together on Instagram in October 2015, and not long after, he started popping up regularly on Tiffany's Instagram.) 

In spite of the fact that he leans left, Mechanic attended the second presidential debate, the 2016 Republican National Convention — where Tiffany addressed the crowd, and Donald Trump's inauguration. Though Mechanic's politics may not align with the first family, he certainly towed the party line at public appearances.

'The best real estate lawyer in the world'

Ross Mechanic's father, Jonathan, who is an attorney with international law firm Fried Frank in New York, met the future president 10 years before their children started dating, when he toured a space inside Trump Tower for Gucci, whom he was representing at the time. The lawyer must have impressed The Donald at that first encounter, because the latter gave him a signed copy of his book, The Art of the Deal and inscribed it to "the greatest real estate lawyer in the world."

Jonathan offered a bit of insight about his son during an interview with Commercial Observer, revealing that his progeny is quite the pool player. "If you play him, keep your money in your pocket," warned Dad.

He has a very good brain

Ross Mechanic is no academic slouch. According to his LinkedIn page, he scored a 2270 on his SATs, and perfect and near-perfect scores on SAT II exams in Math and Chemistry, respectively. He was also a National Merit finalist and a National AP Scholar who parlayed his test-taking skills into an internship at Veritas Test Prep, where he developed materials to help students score high on the SATs.

His ex's bro-in-law hooked him up

During the summer of 2016, Ross Mechanic worked as a data engineer for CADRE, a real estate investment management firm started by Jared Kushner, husband of his ex-girlfriend's half-sister, Ivanka Trump. Kushner currently serves as a senior advisor in his father-in-law's cabinet and has made plenty of headlines for his connections to foreign officials and business leaders.

Living that good life

One look at Tiffany Trump's Instagram reveals that she and Ross Mechanic were not exactly the stay-at-home type. Indeed, they've gone zip-lining and swimming with sharks in Belize; frequented Mar-a-Lago, aka the "Southern White House;" visited the local landmarks of Budapest, Hungary; and of course, hit up some picturesque tropical locales. But let's be real: All of that is nothing compared to the private tours of the White House he's likely gotten since January 2017. Bottom line: the dude gets around.

A sharp-dressed man

Before the snubbing controversy at New York Fashion Week in 2017 made national news, Ross Mechanic sat front row with Tiffany Trump and her mom, Marla Maples, at the Taoray Wang show at Skylight Clarkson Square. It's worth noting that the Chinese designer also created the white, double-breasted, custom coat Tiffany wore to her father's inauguration.

Not-so-rough beginnings

Before he was a Penn student or an intern, Ross Mechanic was enrolled at Friends Seminary, the oldest co-educational Manhattan private school, where he participated in the Mock Trial and Debate Team. The 2013 Friends Seminary grad became one of many famous alumni. Actresses Julia Stiles, Kyra Sedgwick, Liev Schrieber, Olivia Thirlby, and Amanda Peet are all Friends' grads..

Work hard, play hard

Ross Mechanic is definitely as much a part of the social scene as Tiffany Trump, and in addition to his experience in computer engineering and real estate, he also interned with the AIM Hospitality Group in 2014, a job which included promoting parties in New York City and in the Hamptons.


Though they seemed like an Ivy League match made in heaven, Tiffany Trump and her ex-boyfriend, Ross Mechanic, seem to have gone their separate ways. According to a February 2018 report from the Daily Mail, the couple hasn't been spotted together "for months." On top of that, Mechanic set his Instagram to "private" in the fall of 2017 after posting several photos of himself and a brunette — identified by the Mail as twenty-something NYU student Carly Berns — embracing and kissing.

Neither Mechanic nor Trump have publicly commented on their relationship status, but with Tiffany attending grad school at Georgetown in Washington, D.C., and Mechanic remaining headquartered in New York City, some have speculated that the distance could have contributed to their split.