Whitney Port’s Engaged! Help Her Kiss Off Singlehood With These 5 ‘City’ Dating Disasters [Video]

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Whitney Port and Tim Rosenman stroll through the New York City streets in May.

Love is in the air! Like, really in there. Just one month after two of her “Hills” co-stars, Lauren Conrad and Holly Montag, announced their engagements, Whitney Port is now sporting a sparkly new rock as well, MTV News confirms. The fashion designer will marry Tim Rosenman, who worked as an associate producer on “The City.” Congrats, Whit! The thought of all these old friends finding their princes one by one is making us all misty-eyed…

The engagement comes as a bit of a surprise, as Port’s managed to keep her romantic life out of the spotlight since her 2011 split with fellow MTV star, Ben Nemtin of “The Buried Life,” but we couldn’t be happier for the girl who once tripped down the stairs in a full-length gown during a live “Good Morning America” segment. Whit’s certainly kissed her fair share of frogs over the years, and from Mr. LV (that’s Louis Vuitton, okay?) to her double date with Freddie Fackelmayer and his DAD, she definitely deserves the nice dude she’s decided to settle down with.

+ To help her celebrate the big news (and for a fun blast from the past), check out five of Whit’s “City” dating disasters below, and leave your congrats for the happy couple in the comments!

The slangtastic blind date from hell: Whit got set up on a blind date with Patrick, a kid with so many obscure abbreviations in his back pocket, he’d give “Awkward” gossip Tamara a run for her money.

Jay and Whitney call it quits: Having a rock star boyfriend ain’t all it’s cracked up to be, and when Whitney and Jay tried to work out their lifestyle differences, it ended in a teary goodbye.

Freddie turns dinner into an awkward three-way: Two’s company and three’s a crowd, and when Freddie brought his dad along to what was supposed to be an intimate dinner with Whitney, things got puh-retty uncomfortable.

Alex accuses Jay of cheating: While out at a club, Alex lunged to Whitney’s defense after rumors of Jay’s wandering eye found their way to the group. The two guys exchanged some choice words, and Whitney had no choice but to watch it unfold.

Whit finds out that Freddie’s a total player: As if Daddy Warbucks tagging along on their date wasn’t bad enough, the Fackelmayer fam continued to shake up Whit’s relationship with Freddie in the Hamptons. When Fred’s little brother, Harry, started hitting on Whit, Freddie got pissed…so Harry retaliated by telling her that Fred had a girlfriend. Sibling rivalry at its best, people.

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Photo: Getty Images