Vanessa Simmons may not have had a childhood like most of ours (things are bound to be a little different when you're the eldest daughter of hip-hop legend Reverend Run of Run-DMC), but that doesn't mean she didn't experience the same growing pains we all do.

Just like everyone else, Vanessa went through perhaps the single worst rite of passage for any teen: the first heartbreak. The actress/reality star sat down with MTV to open up about her painful split with her first true love for the latest episode of "When I Was 17," which also features [article id="1662930"]?uestlove[/article] and [article id="1662924"]Christina Perri[/article].

As a teen, Vanessa had a serious boyfriend, whom she described as her "high school sweetheart." She reminisced with a laugh about her puppy love with her then-boyfriend, saying, "You know, you're thinking marriage."

But poor Vanessa wasn't heading down the aisle anytime soon as her boyfriend soon broke up with her. Still, the worst was yet to come for the "Run's House" star. "Cut to not even a week after we broke up, he walks into homeroom. He has a necklace with another girl's name on it," she recalled. "Everybody else knew that he was with this other girl, except me. Apparently they were, like, really into each other and kind of serious and I was like, 'When did this happen? Over the weekend?'

"It felt like my heart literally was breaking," the 27-year-old beauty continued. And while she did commit the ultimate dumped-by-a-jerk sin by getting back with him, something she said she now regrets, Vanessa is truly having the last laugh.

"I ended up breaking up with him at the end of senior year anyway," she told MTV, adding, "[It] doesn't even matter."

Check out the all-new episode of "When I Was 17," featuring Vanessa Simmons, ?uestlove and Christina Perri, on Saturday, April 30, at 11 a.m. ET on MTV.