Whitney Port’s Fiancé Proposed TWICE, And How He Did It Was Predictably Perfect

The 'Hills' and 'City' gal had two memorable engagements!

Whitney Port officially, and happily, kissed away her single days more than a year ago when Tim Rosenman popped the question -- not once, but twice!

The handsome duo, who adorably met during the fashion designer's Big Apple days on "The City" (MTV bringing people together in holy matrimony!), have remained relatively mum about the heartwarming details surrounding their multiple engagements -- that is, until now.

The erstwhile "Hills" starlet tells all on her website, first revealing that the TV producer intended to propose during a trip Down Under at Sydney Harbor. But things took a slightly different turn after she overheard him talking on the phone with his boss -- the night before they were leaving town.

"I swear I wasn't being nosey at all!" the former "Teen Vogue" intern writes, adding that they were enjoying "Shark Tank" during their dinner and were in very close proximity to one another during his intended confidential chat. "That's when I heard his boss say something like, 'Good luck with Whit with whatever you decide to do in Australia.'"

Whitney Port's Instagram


And that's when panic set in for our girl. "My stomach immediately dropped. I thought to myself, 'Does he need to talk to me about something? What the f does he need luck for?'"

But being the strong-minded lady that she is -- this is the same determined gal who could hold her own with fashion titans Lisa Love, Kelly Cutrone and Diane von Furstenburg -- she was vocal about what she just caught wind of during the conversation. Little did the style maven know what was coming her way in that very moment.

"I immediately asked him and he tried to brush it off, but I just couldn't let it go," the blond beauty admitted. "He could see the mental torment I was putting myself through, so he finally gave in. He got down on one knee and proposed! It was so beautiful." Shortly afterward, the two went to her mom's home -- and popped a bottle of bubbly, of course -- then jetted out of town the next day as planned.

Whit explains that her future hubby intended to ask for her hand in marriage during the vacation and was collaborating with jeweler Ron Bensimon on a beautiful ring. But since the sparkler had not yet been purchased -- a sketch of the original idea is featured below -- the SoCal native was able to give her love a little insight into what she wanted for her special bauble (oval shape and rose gold).

Whitney Port's website


Eventually, the special piece of jewelry was complete and flown to Oz -- and that's when Tim decided he wanted to make things really official.

"He came back to our hotel room, got down on one knee, presented me with the most beautiful ring I had ever seen and popped the question!" she gushed. "How many girls get to say they had two proposals?! I feel so lucky, and I wouldn't change a thing about our story!"

Wish we had a front row seat to all of the action (say on, oh "The City," but c'est la vie). Stay tuned to MTV News for any updates on Whit and Tim's upcoming big day!

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