Random Older Celebrities Who Actually Dated Teenagers (20 items)

(#14) Nick Lachey
- 49
While most people remember this couple for their post-marriage show, The Newlyweds, not many people recall that when these two met in 1998, Lachey was 25 and Simpson was 18.

As we all know by now, Lachey and Simpson's three-year marriage ended in divorce in 2005.
(#8) Taylor Swift
- 33
Pop sensation Taylor Swift had a brief relationship with 17-year-old Conor Kennedy, grandson of Robert F. Kennedy, in the summer of 2012. The duo was introduced by mutual friends and quickly became inseparable, often seen together at various Kennedy family events in Cape Cod. Swift even penned a song about their whirlwind romance, titled "Begin Again." However, the pair's relationship fizzled out as quickly as it began, and they split later that same year.
(#20) Justin Gaston
- 35
Model and musician Justin Gaston gained public attention when it was revealed that he was dating a then-15-year-old Miley Cyrus in 2008. The couple met while Gaston was working as a contestant on the reality show Nashville Star, which Miley's father, Billy Ray Cyrus, was hosting. Despite their 5-year age difference, Cyrus and Gaston frequently attended events together and were often seen out on the town. However, their relationship was short-lived, and they split up later that year.
(#5) Jerry Seinfeld
- 69
At the height of his Seinfeld fame in 1993, Jerry Seinfeld approached Lonstein, then a 17-year-old high school student, walking around in Central Park. After getting Lonstein's number, the pair started dating quite seriously despite the age difference (Seinfeld was 38 at the time). Lonstein was a senior, and the two continued dating for the four years she attended college.

Seinfeld spent much time defending their relationship, but the two split for good in 1997. Shortly thereafter, Seinfeld met his current wife, Jessica Sklar. The pair have been married for more than 20 years.
(#16) Chad Michael Murray
- 42
Kenzie Dalton lived out every high schooler's dream when 25-year-old television star Chad Michael Murray proposed to her in 2006. Literally - because she was still a senior in high school. Murray met Dalton after she appeared as an extra on One Tree Hill.

Before ultimately parting ways, the pair remained engaged for seven years - incidentally the same number of years as their age gap.
(#7) Luc Besson
- 64
After his 1991 divorce from Nikita star Anne Parillaud, director Luc Besson, 32, started dating 15-year-old Maïwenn Le Besco. The couple married the following year while Maïwenn was pregnant with their daughter. Besson later claimed that their relationship inspired his film Léon: The Professional (1994), which followed an emotional relationship between an adult man and a young girl.

Besson and Le Besco were married until 1997 when he became involved with The Fifth Element actress Milla Jovovich, who was in her early twenties at the time. Besson and Jovovich were married from 1997 until 1999, when they divorced.