Whitney Port is No Longer Holding Anything Back

When Whitney Port steps up to a microphone these days, her filter is firmly switched off. 

The With Whit host’s latest sit-down on Live from Bed with Jade Iovine proves just that—the original reality-TV cool-girl breezes past niceties and heads straight to the point. From debunking The Hills myths to speaking unflinchingly about miscarriages and surrogacy, the ex-Hills most sensible star is serving honesty with zero chaser these days.

After having to play nice with MTV’s manufactured drama for far too long, Port has traded her carefully curated image for something infinitely more valuable: the freedom to tell the truth.

The reality about reality TV

More than a decade later, fans still debate how “real” MTV’s glossy hit was. Port echoed what her ex-costar, Spencer Pratt, shared a few weeks before on Not Skinny But Not Fat: “Parts of it were definitely produced, but it wasn’t all fake.” 

The Paris internship was one legendary plot twist. “I didn’t really go to Paris,” Port reveals, clarifying that she only went for a couple days that summer. “But I didn’t actually have the summer internship,” she says. She even shot an airport goodbye scene in full travel chic—then headed straight home. 

Still, her on-screen friendship with Lauren Conrad wasn’t scripted. “I was really there as her confidant, as her, like, therapist in the office. That was my role, and I knew that,” Port says.

Getting candid about fertility and grief

Port has endured five miscarriages, two failed surrogate transfers, and the emotional roller coaster that follows each loss. Consequently, she’s now going the surrogacy route, revealing, that her and her husband are “in the process of finding the right person now.” 

Iovine’s advice to friends who announce pregnancies around someone struggling to conceive (“Don’t make it weird”) landed with Port, who adds that every reaction is valid yet temporary. Her mantra for anyone navigating infertility is simple: “Everything is a phase.”

Port also reveals that her fertility setbacks trigger “that feeling of loss” around her father, who died in 2013 after a year-long battle with kidney cancer.

Her refreshingly honest take on gifts, glamour, and growing up

Port may design clothes and sit front row at Fashion Week, but she still struggles like the rest of us, and is admittedly still the girl who loses everything in hotel rooms. When asked if she’s a good gift-giver, she sighs, “Not really, honestly. Because I lose everything.” Big-ticket splurges don’t impress her either as she says she’s not much of a “a curator of expensive things that I want…that hasn’t really hit me yet.” Instead, she champions thoughtful gestures and experiences over price tags, proving her maturity well past the Teen Vogue closet.

The same irreverence shows up in Iovine’s life-rule lightning round, where Port deadpans about manners and house-guest etiquette. If millennials needed permission to embrace chic loungewear and honest conversations, they just got it.

What’s next for Whitney Port

Between filming candid YouTube reaction videos with husband Tim Rosenman (the couple just launched Whitney Forever for more exclusive content you can’t get anywhere else), running her clothing label CozeCo, and hosting the With Whit podcast, Port keeps her plates spinning—and, yes, occasionally drops one.

But that’s why her voice resonates. Port speaks to women who’ve outgrown the need to have it all figured out, who can hold authenticity alongside ambition. The most interesting thing you can do is stop trying to be interesting.