VIDEO: Watch Whitney Risk It All On Tonight's City Finale!

Whitney Port's always had a good head on her shoulders. Smart, sensible and quietly ambitious, she started out as Lauren Conrad's top advice giver-outer, survived a stint as Erin Lucas' crying shoulder and finally evolved into Roxy Olin's best friend and closest confidante. And while she's taken a few big leaps of faith in her life (like moving across the country to New York!), she's mostly skated by on her hard work, dedication and slow-and-steady-wins-the-race approach.

'Course, that could all change tonight ... if Kelly Cutrone has her way. On the City fall finale, the brazen boss lady's pushin' Whitney to bet it all for one shot at greatness. But is the budding designer ready to risk her rep on a whim? Watch Kelly encourage Whit to make the ultimate gamble, then tune in tonight at 10:30pm to find out whether our gal will be playin' it safe -- or going for the gusto.

+ Don't miss a second of the Hills/City finale extravaganza! Watch the pre-show special at 9pm (Cast Confessions: From The Hills To The City), stay tuned for both shows' drama-filled finales, then stick around for the live post-game report (hosted by the After Show's Jessi and Dan) at 11pm!