Lance Armstrong and Ashley Olsen may be Hollywood’s most unlikely couple since Tom Cruise and Katie Holmes. The 36 year old retired professional cyclist and the 21 year old mogul were spotted twice in one week out together in New York City hotspots.

First on Monday the pair were seen together at the Rose Bar in the Gramercy Park Hotel, and then again at the Waverly Inn & Garden on Bank Street in NYC. While their public displays of affection were not caught on camera, several eye witnesses were not ashamed to declare that the couple made out all night. Whether or not the pair turn into a full-fledged couple will only be seen in time, but surely it will receive much attention, simply because of the odd matching.

Lance Armstrong is best knows as the 7 time Tour De France winner from 1999 through 2005. While his professional success is amazing, it was made more so by his triumph over testicular cancer just 3 years before his first Tour win. Armstrong’s personal life has not been free of publicity after his divorce from wife Kristin (Richard) Armstrong in 2003 with whom he has 3 children, Luke (now 8), and twin girls Isabelle and Grace (soon to be 6). The fact that his son Luke is closer in age to Ashley Olsen than he is, is among one of the most controversial aspects of their hook-up.

Most recently, Armstrong has been linked with singer Cheryl Crow, though their relationship ended before the couple was set to marry in early 2006, and fashion designer Tory Burch. Armstrong and Burch ended their one year relationship in October of 2007, and less than one month later Lance was seen out with Olsen.

Ashley Olsen is most recognized as former character Michelle Tanner in the 90s family sitcom, Full House. Since the end of the 8 season show, Ashley and her twin sister Mary-Kate have skyrocketed up the mogul list after taking control of their company, Dualstar. While the pair has made millions from their straight-to-video releases and extensive line of pre-teen and early teen clothing, accessories and dolls, they have attempted to shift their image to a more high-end market. With a focus on adult fashion, the pair has launched a new branch of their The Row clothing line with the Elizabeth & James collection which is named after the pair’s siblings. The duo has recently began to perform on the big and small screen individually, with Ashley set to appear in the 2008 film The Informers with Billy Bob Thornton.

Only time will tell if the Armstrong and Olsen hook-up will be anything more than a few nights out on the town, or if it will develop into anything more serious. Do you have an opinion on the latest Hollywood hook-up? - if so, head on over to the Entertainment News Forum and share your thoughts!