Rachel Uchitel

Rachel Uchitel is making headlines again. 

The good news? This has nothing to do with riding Tiger Woods. The bad news is that if Page Six Magazine has quoted her accurately, she is a terrible person.

To sum up, she's glad her fiance died because she'd be fat otherwise. Nice.

Uchitel said the death of her former fiance, investment banker James Andrew O’Grady, who perished in the September 11, 2011 attacks, was meant to be.

“I believe Andy was meant to die because he was too good,” she said. “I’m almost happy it ended the way it did because I’ve learned so many lessons from him."

What would those valuable pieces of knowledge be?

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A report surfaced last weekend that Elin Nordegren's new boyfriend, Jamie Dingman, used to date Rachel Uchitel, Tiger Woods' shady #1 mistress.

It seems almost too coincidental, but apparently Elin did not know about this prior to TMZ's report, and she is pissed now. We can't imagine why.

To hear sources close to Jamie Dingman tell it, his involvement with Uchitel was in fact real, but not as serious was what was initially reported.

Sources claim Jamie only hooked up with Rachel twice in October 2009 (two months before the Woods scandal erupted), but that they never had sex.

TMZ says Rachel and Jamie initially became involved professionally, working on a new investment business. The nature of the business is not known.

In any case, the two both stayed in the Miami home of Chris Barish, the third partner in their prospective business, for 2-3 weeks in October 2009.

During that stretch, Jamie came into Rachel's room late night and hooked up with her twice. Rachel discussed it with Barish the morning after each.

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Rachel Uchitel has repaid much of the money Tiger Woods paid her to keep quiet in the aftermath of their affair, and may sue Gloria Allred as a result.

Huh? Relax. It's even more confusing than you think.

In early 2010, Allred negotiated a $10 million settlement for Rachel, who had planned to hold a news conference and detail her relationship with Tiger.

The mammoth payoff included a confidentiality agreement, which prohibited Rachel Uchitel from talking about Tiger. Ever. Here's where it gets dicey:

The confidentiality clause works the way you think it does. If Rachel spoke about Tiger, she'd have to pay back the money, as well as potential damages.

Several months ago, Tiger's lawyer, Jay Lavely, contacted Gloria regarding Rachel's appearance on Celebrity Rehab, saying they planned to sue over it.

While she never talked specifically about Tiger on the VH1 show, Uchitel's reality show treatment "addiction to love" royally pissed off Woods' camp.

Rachel felt strongly she had not violated the agreement, but Gloria convinced her she would lose if Tiger's attorney pursued the case against her.

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Before he began dating Elin Nordegren, Jamie Dingman and Rachel Uchitel were an item. Yes, the same woman whose affair with Tiger Woods was exposed in November 2009, sending him fleeing in his car and ... you know the rest.

Didn't see that one coming, did you?

Jamie Dingman, whose dad is a billionaire tycoon, has been dating Elin Nordegren for several months. Prior to Elin, Jamie and Rachel dated fairly recently - there was even some overlap with Tiger, which Jamie was aware of!

When Rachel Uchitel was getting more serious with Tiger, Jamie reportedly joked. "That's okay. I'll date his wife, Elin." It gets weirder still:

At the time the Tiger scandal broke, they were living together in Miami! 

One last bizarre connection comes from Jen Madden, the girl who sold the Woods story. Staying at her friend's home, she learned about Rachel Uchitel's affair with Tiger when she overheard her talking about it ... with Jamie.

No clue if Elin Nordegren is aware of any of this, but if she's not, we can't imagine it's going to go over too well when someone clues her in.

Then again, maybe it's a little bit of payback.

Who would you rather ...

Best known for going under the covers with Tiger Woods, Rachel Uchitel is now going undercover as a private investigator! For a new reality show!

You can't make this stuff up.

Rachel Uchitel recently became a licensed P.I., which certainly puts her primary skill set in life - sneaking around - to good use. Way to go Rache!

Uchitel has a deal for a docu-drama on her life with Atlas Media Group.

"I wasn't interested until Atlas came along and agreed with me the only way to do something was if it was a 'true' reality show," Rachel said.

"I'm doing PI work now and it's stuff that would make for great TV."

A former professional mistress, Rachel Uchitel says she won't be going after cheating spouses, but will branch out and try to concentrate on cases of missing people, child custody claims and financial forensic work.

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Rachel Uchitel, Tiger Woods' famous mistress, has scored herself a new boyfriend.

Not only that, but they're already living together! Matt Hahn, a 25-year-old insurance underwriter and former Penn State football standout, is totally "the best thing that's happened to me in as long as I can remember," Uchitel said.

At least since her affairs with Tiger Woods and David Boreanaz.

Amazingly, Matt Hahn is not a celebrity OR married to someone else!

Rachel Uchitel recently embarked upon a new career as a private investigator in NYC, where she owns the $2 million Park Avenue apartment she shares with Hahn.

Tiger bought them a nice love nest, it sounds like.

[Photos: Pacific Coast News]

Rachel Uchitel became infamous in 2009-2010 because, well, the woman is a serial, professional mistress. But she's focused on a new career now.

One which still involves sneaking around, interestingly.

In an ironic twist, the woman whose clandestine relationships with David Boreanaz and Tiger Woods gained national attention wants to be a P.I.

We can't believe it either, Tiges.

“I decided to go back to school and get my private investigation license! I’ve learned to shoot a weapon. I had to Taser someone,” Uchitel told Fox 411.

“I even had to get pepper sprayed, so I know what the effects are."

Somewhere, Elin Nordegren wishes she could've done the honors.

"I’ve already gone under cover," says the aspiring investigator. "In court, we actually do real stuff for the investigator who’s teaching the class."

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Will Rachel Uchitel and Tiger Woods reunite at Donald Trump's New Year's bash next weekend? Stranger things have happened ... well, presumably.

The world's top golfer and his top mistress have both been invited to The Donald's annual New Year's Eve bash at his Mar-a-Lago estate in Florida.

If Trump is serious about running for president, he could certainly show his powers of unification and bringing different parties together with this ...

THE UNITER: Trump would love to have Tigitel on hand.

As for the oft-maligned Woods, with whom he is acquainted, Donald says "I did invite him. I'm the only guy who has tried to defend him this year."

Rachel Uchitel, as usual, is more complicated. She was reportedly on board for the cast of Celebrity Apprentice this year until DT pulled the plug.

As far as New Year's, has a "blind date" with a guy in the New York fashion industry whom Donald invited, and Rachel is coming as the plus one.

Donald says there's no hard feelings and that "she's absolutely welcome." No word if he also plans on inviting Rex Ryan's wife as a publicity stunt.

A new season of VH1's Celebrity Rehab with Dr. Drew and the romantic life of former Tiger Woods mistress Rachel Uchitel is the center of attention.

With no usage of the words "Tiger" or "Woods" of course.

Uchitel told Dr. Drew she bypasses the whole dating process for "intense, overnight" connections, he called it "love addiction" and encourages her to chill.

Rachel said men she pursues are often birds of the same feather - as in married, rich and famous - and she's "too much for them to handle." Rowr!

Here's an interview with Uchitel regarding her Rehab stint ...

Rachel Uchitel Speaks Out

In a rare TV interview, Tiger Woods' famed mistress Rachel Uchitel spoke on the Today Show about her addiction to love and how that led her astray.

Appearing alongside her Celebrity Rehab mentor, Dr. Drew Pinsky, Rache promoted her stint on the VH1 program and explained why she went on it.

"I knew that I needed help," Uchitel, who claims she went on the program to deal with her love addiction. "And I wanted to get it from Dr. Drew."

Uchitel she needs help ... and had some lip injections.

The 35-year-old all-pro mistress also said she was being treated for addiction to Ambien and other prescribtion medications, which she did not identify.

Dr. Dew said Rachel Uchitel's condition is partly triggered by traumatic events in her past, such as the premature deaths of her father and fiance Andy.

She was set to get married before he perished in the 9/11 attacks.

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