R. Kelly: When R. Kelly was exploring his love for teenage girls, we didn’t have access to the plethora of information that can now be found on the internet. Luckily for the R&B singer, his romance and marriage to 16-year-old singer Aaliyah was kept under wraps for many years, but his sex romps with other teens would land him in a heap of trouble.In 2002, a sex tape was leaked showing Kelly engaging in sex with a girl who was just 14 years old. Although the victim claimed the sex was consensual, charges were brought forth, and the singer was eventually acquitted of all counts. In 2003, another video of Kelly having sex with a minor was discovered, but those charges were thrown out. Kelly was married throughout all of the underage sex and child pornography court trials. Thankfully, his wife (now ex-wife) was of the legal age of 22 at the time of their wedding day.

Chad Michael Murray: One Tree Hill star Chad Michael Murray fell in love with a 17-year-old extra, Kenzie Dalton, on the set of the popular drama. Murray was 24 when he began dating the blonde teen, and he proposed to the high school senior a year later. Although Dalton accepted the proposal, their 7-year engagement finally ended, and the two went their separate ways.

Jerry Seinfeld: In 1993, 38-year-old Jerry Seinfeld met and fell in love with Shoshanna Lonstein, who was a 17-year-old high school senior. The two dated for four years, then in 1998 he met his current wife Jessica, who is 17 years his junior. They got married on December 25, 1999 and are still together to this day. The couple has three children together.

Doug Hutchison: The 50-year-old was a relatively irrelevant actor until he began dating 16-year-old Courtney Stodden. The two were married fairly quickly after Stodden’s parents signed off on their union. The two have flaunted their May-December romance all over the tabloids and reality television, and the world breathed a collective sigh of relief when the two announced their separation in November 2013. Finally, the crazy train was over! But not so fast, the couple has since reconciled and they celebrated their 4-year anniversary this year.

Joel Madden: Many people completely glaze over the fact that Joel Madden dated 16-year-old Hillary Duff when he was 26-years-old. The two kept their relationship on the down-low until Duff turned 18, but by the time, their romance was on the verge of fizzling out. Duff later gave an interview to Cosmopolitan magazine and revealed she had lost her virginity to Madden. Um, gross.

Kobe Bryant: As a 21-year-old in the NBA, he pretty much had his pick of any woman, but his heart was set on one girl in particular, 17-year-old Vanessa Cornejo. Cornejo was a high school senior at the time and Bryant quickly won her over after picking her up from school in one of his flashy, expensive cars. The basketball payer proposed after just six months of dating, and although they’ve had a few bumps in the road including a divorce filing, they’ve managed to work things out and stay together for 14 years.

Justin Gaston: Knowing what we now know now about Miley Cyrus, it’s really no surprise she was involved in a romance with an older guy when she was just 15. Cyrus dated Justin Gaston when he was 20, and the two even met through Cyrus’ father, Billy Ray, who signed off on their relationship. The two later called it quits, and Cryus’ love life has been all over the place ever since.

Paul Walker: Following the actor's 2013 death, rumors of a relationship with an underage girl began to surface. Walker was allegedly dating 23-year-old Jasmine Pilchard-Gosnell, and the two were reportedly engaged at the time of his death. They had been together for seven years at the time Walker was killed in a horrific car accident in Valencia, CA.

Wilmer Valderrama: That ’70s Show actor is notorious in Hollywood for dating young girls. His first notable underage romance was with Mandy Moore who was 16 at the time. Valderrama was 20 when they began dating, so the age difference wasn’t that bad. But then, four years later, he hooked up with 17-year-old Lindsay Lohan when he was 24 years old. The now 35-year-old actor is dating Demi Lovato, and the two began their romance when Lovato was just 17 years old.

Sonny Bono: The late singer and politician is well known for his romance with Cher. Many people don’t realize (or choose to forget) that Cher was only 16 years old when she met 27-year-old Bono. The two soon began dating, and Bono helped his teenage girlfriend get backup singing gigs with some of the hottest groups in the 60s before they formed their own singing duo. The couple was married in 1964 when Cher was 18, and they divorced 11 years later.