Hugh Hefner and Crystal Harris Engaged: How Does Holly Madison Feel?

Holly Madison is Reportedly Upset Over Hugh Hefner's Engagement

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Playboy founder Hugh Hefner proposed to girlfriend Crystal Harris, 24, over the Christmas holiday with a 3 1/2 carat brilliant-cut diamond ring reportedly worth $90,000.

"After the movie tonight, Crystal & I exchanged gifts. I gave Crystal a ring. A truly memorable Christmas Eve," Hefner, 84, tweeted on Dec. 25. "When I gave Crystal the ring, she burst into tears. This is the happiest Christmas weekend in memory."

Harris appeared as Playboy's Playmate of the Month in December 2009 and became one of Hefner's three girlfriends -- along with twins Karissa and Kristina Shannon -- after his "Girls Next Door" girlfriends left the Playboy mansion.

"For those of you who have been asking to see my ring here it is... My engagement ring from my love @hughhefner," Harris tweeted on Dec. 26, along with a picture of the stunning ring.

Hugh Hefner and Crystal Harris Engaged: What About Holly Madison?

We're happy for the 84-year-old Hefner and his bride-to-be, but we can't help but wonder what his former flame Holly Madison thinks of the upcoming wedding. Madison found fame as Hefner's main girlfriend and star of E!'s "Girls Next Door" along with Kendra Wilkinson and Bridget Marquardt. Both Wilkinson and Marquardt have expressed their happiness for Hefner and Harris, but Madison hasn't made a peep. Why?

Chicago Times columnist Bill Zwecker wrote that Madison is more than upset at the pairing.

"She can't believe Crystal was able to get Hef to agree to something she had tried for so long," a source close to Hefner told Zwecker.

Madison spent six years as Hefner's main squeeze and it wasn't a secret that she wanted a ring from the Playboy mogul. She brought it up several times on "Girls Next Door" and talked about it openly in interviews.

"Even after Madison's fling with magician Criss Angel — supposedly done to make Hefner jealous — and Hefner's plea for her to come back to him, he still never proposed marriage or gave her a ring," Zwecker wrote.

Hefner brushed off Madison's requests, saying he wouldn't marry again after two failed marriages.

"I love Holly very much and I think we're going to be together the rest of my life, but marriage isn't part of my puzzle," Heffner said during a 2008 interview. "It's not a personal thing; I just haven't had much luck with marriages."

Madison: I Wanted a Baby With Hefner

Madison even tried to lure Hefner into marriage with a baby.

"I devoted 100 percent of myself to Hef the whole time we were together," Madison told InTouch after their split. "We tried for me to get pregnant by in vitro fertilization, because it wasn't going to happen the old fashioned way."

The relationship fizzled after the IVF treatments failed to produce a pregnancy.

"When the IVF didn't work out after months of giving myself injections every day and feeling horrible, the clinic informed me it wasn't possible because he was too old. I feel they were just after my money because they knew there was a 99-percent chance it was impossible."

Afterward, Madison briefly dated illusionist Angel and rocker Benji Madison and now claims she'll never date again.

"I don't need a man. I'm really happy with myself and being with my friends."

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