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Every time the public has come to expect him to finally have found the 'one,' we get another one of those breakup tabloids. Many of you may remember the name Rachel Uchitel from the Tiger Woods saga. Jeter and Uchitel spent time together back in 2008.

Uchitel was rumored to appear for Jeter and Enriquez briefly dated back in 2001, after Alex Rodriquez supposedly introduced the two following his own relationship with the star.

As everyone dreams of having that perfect moment when doing the deed for the first time.

Something that’s romantic and with the person they love.

After her grandmother stepped in to bankroll her first album 19-year-old Simpson found herself struggling against the massive success of edgier Billboard-toppers Spears and Aguilera. I really feel equipped for what's going to come." But there were growing pains, too.

When you are a legend in your sport, you get rewarded with millions of dollars - and a revolving door of hot girlfriends.

We have seen Jeter with numerous ladies that we expected - and often hoped - he would finally settle down with. Jeter and Dutta were spotted together shortly after she won the 2000 Miss Universe Pageant. Dutta is one of the bigger stars in her native India courtesy of roles in Bollywood hits such as "Om Shanti Om" and "Billu Barber" which many of you may have seen.

Unfortunately, not all ends up perfect and romantic.

Want to now how some famous celebrities lost their innocence and at what age? Here’s the 20 Celebrities who Revealed how they Lost their innocence.

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