Jason Segel Dating UES Socialite Secretly! 10 Girls We Think It May Be

Rumor has it that I Love You Man‘s, Jason Segel has been booking rooms under the pseudonym Sydney Fife, at the Bowery Hotel. Why? To secretly date an Upper East Side socialite, of course! With no confirmations on who the lucky lady is, here are our best guesses as to who Segel might be secretly seeing.

Amanda Hearst:

Amanda Hearst is not only an heir to the Hearst publishing throne, she’s also an IMG model. We think she and Segel would make a perfect couple.

Arden Wohl

With her trademark headbands and bohemian style, Arden Wohl stands out in the New York City socialitescene. Graduating from NYU’s Tisch film school, she has produced a few short films and is an avid supporter of the Nest Foundation, a youth organization that raises awareness about the sexual exploitation of children. Wohl’s track record of being a free-sprited, trust-funded, film funding gal, may be just enough to deem her the next Mrs. Segel.

Olivia Palermo

We’ve come to have a love/hate relationship withOlivia Palermo over the past few years. From her stint at DVF with Whitney to her constant battles with Erin as the Accessories Editor at Elle, we can’t say we always support her career moves. However, we can always support her fabulous wardrobe choices! Do you thinkPalmerois datingSegel? We think it’s likely.

Fabiola Beracasa

Contributing blogger for Interview, Fabiola Beracasa, is one fabulous socialite. With impeccable style and too many connections in the fashion industry to count, we hope that Segel and Beracasa go on secret shopping (and smooching) escapades throughout the city.

Byrdie Bell

Byrdie Bell, actress and fashionista, may have it all — that is, if she’s secretly dating Jason Segel. With a flourishing career, fabulous closet, and cool demeanor, we can’t help but wonder if she’s the one sneaking around the Bowery.

Tory Burch

Tory Burch, designer and New York City socialite, has had her fare share of men. As Burch is divorced with children, we wonder if Segel spends his time babysitting the kids? What do you think; is Tory Burch Segel’s secret socialite?

Bettina Zilkha

Bettina Zilkha is virtually inescapable within the NY social scene. After writing Ultimate Style: The Best of The Best Dressed List, her career as a writer came to a halt, but her socialite status sky-rocketed. We can see this chic social on Segel’s arm easily.

Victoria Traina (right)

Commonly spotted with the Olsen twins, Victoria Traina (pictured with sister Vanessa above) is definitely prominent on the social scene. I don’t think Segel would mind if Traina showed up every once and awhile with Mary-Kate tagging along to triple date. Do you?

Rebecca Guinness

Rebecca Guinness, is a socialite and scribe forVanity Fair Daily. She also has her own jewelry line that houses some pretty wearable pieces. Seemingly more laid back than most of New York’s socialite crew, we can pictureRebeccaand Jason sitting down at her favorite restaurant,Giogione, eating pizza and cracking jokes. We know she recently moved overseas, but is it possible that she’s come back to spend some quality time with her potential lover?

Tinsley Mortimer

Tinsley Mortimer may be the first person that comes to mind when you think of New York City’s socialite ladies; however, she and funnyman Segel couldn’t be more different. But who knows? Opposites do attract.