15 Celebrity Couples That Are Just Plain Odd

2. Ashley Olsen and Lance Armstrong

Though their encounter was a brief one, it was a strange one nonetheless. In 2007, Olsen and Armstrong were noticeably cozy in public before hooking up for a rendezvous at the Gramercy Park Hotel.

However, things must not have gone as well as they had planned because after only a short time together, the unlikely pair decided not to pursue a more serious relationship and parted ways. The disgraced cyclist was then uncovered as having a romantic entanglement with the 21 year old.

Since Armstrong is 15 years senior to Olsen, he was warned that this relationship might tarnish his public image – which, ironically, actually became pretty tarnished after he admitted he had been using performance-enhancement drugs. The Tour de France star was warned by his friend John Korioth, the head of Armstrong’s cancer-fighting Livestrong Foundation, that his May-December romance could damage his work on fighting the disease.

Armstrong then told his long-term friend to bugger off, because Olsen was 21 at the time, making the relationship completely legal. She was reported sitting in his lap in a the aforementioned New York City club, while drinking red wine and making out more than half of the evening, and leaving at two.

Apparently, the pressure from his public image managers became too much to deal with, and he ended the short affair. The father of five is currently in a long-term relationship with Anna Hansen whom he met through his charity work.

He established the Livestrong Foundation in 1997, after he was diagnosed with testicular cancer. After he admitted he used performance-enhancing drugs in Oprah interview, he was stripped of his seven Tour de France titles.

The truth about the affair came out in Juliet Macur’s book Cycle Of Lies, which is about the thirty-six-year-old cyclist. Recently, Ashley, who has since turned to designing, has been spotted with her sister, who also has a bit of a knack for the older fellows.