Inside Vanessa Trump's Messy First Relationship

Vanessa Trump's first love quite literally hit her in the face when she least expected it. Speaking to Page Six in 2018, her now ex-beau, Valentin Rivera, recalled that his path crossed with Trump's when they were just fifth graders attending a school carnival. The future couple's initial encounter was considerably less than perfect as Rivera threw a water balloon at her, and she didn't hesitate to immediately rat him out for it. Naturally, the unlikely pair didn't make each other's acquaintance afterward. 

In the meantime, Rivera was sent to a juvenile correction center after getting into a scuffle with some kids. The duo later wound up at the same house party when they were 15 and started dating shortly after. Everything went smoothly for a year, but their happiness came to a screeching halt when Rivera received a maximum prison sentence of four years for assault. However, it seems like Trump, who was attending a prestigious private school in New York at the time, wasn't fazed by her beau's dodgy reputation. 

In fact, a friend of hers told GQ that she wore it like a badge of honor. "She talked with an urban, gangster accent," the confidant disclosed. "She wore big hoop earrings, hair slicked back. [...] She was somebody who went out of her way to intimidate people by having a scary boyfriend that could hurt people." Meanwhile, in Rivera's Page Six interview, he shared that his former girlfriend even visited him at Rikers Island prison before Rivera was sent away to a maximum-security juvenile prison. 

Unfortunately, as Valentin Rivera's explained to Page Six, Vanessa Trump wasn't able to visit him much after he was transferred to the youth prison to serve the rest of his sentence because her mother barred her from doing so. However, 15-year-old Trump managed to stay in touch with her beau through letters, and it seemed like she was actively planning their future together. In one love letter shared by People, she penned, "My 18th birthday, you'll be back in my arms, my prom, and I want to get pregnant and have a baby with you after January." It continued, "I want to get pregnant so the baby is born after I graduate since it takes 9 months." 

In fact, even Rivera acknowledged that Trump was eager to tie the knot and have several children with him. Other letters showcased her desperately longing for his return and urging Rivera to remain on his best behavior throughout his sentence. Ultimately, Rivera was released after serving 16 months. However, he didn't stay out of trouble, joining a street gang called the Latin Kings after catching their eye in prison. Still, the young Trump wasn't deterred. She even accompanied him to the gang's meetings and drove him around while Rivera tackled their errands. 

As he told Page Six, "She was fascinated. [...] She liked the street life at the time," adding, "She liked that type of environment — being around gang members and stuff."

In Valentin Rivera's Page Six interview, he confirmed that, against all odds, his relationship with Vanessa Trump managed to survive the natural ebbs and flows of life as they grew into adulthood together. However, everything changed in May 1998, when the New York Post reported that Vanessa, then a 20-year-old model, had been spotted cozying up to none other than Leonardo DiCaprio. Naturally, Rivera wasn't best pleased and swiftly ended things. Unfortunately, his fellow Latin Kings also learned of Vanessa's supposed indiscretion and poked fun at Rivera's misery by re-enacting the iconic "I'm flying!" scene from "Titanic" and belting out Celine Dion's "My Heart Will Go On." Ultimately, it doesn't seem like Vanessa and DiCaprio's rumored relationship went anywhere. And, in 2003, Vanessa and Donald Trump Jr.'s relationship began when they met at a fashion show. 

Speaking to The New York Times, the former model recalled that Donald Trump played matchmaker by introducing his eldest son to her. The pair had a short conversation and went their separate ways, only to meet again at a party a few weeks later. They started dating shortly after, and according to GQ, Donald learned that she had dated Rivera after conducting a deep dive into Vanessa's past. However, when the former president brought up their relationship, she dubbed it a lie. Don Jr. and Vanessa tied the knot in 2005 and welcomed five children in the following years. However, Vanessa supposedly found out Don Jr. was cheating on her and they divorced in 2018.