Lindsay Hubbard’s Dating History: Bravo Men, Boyfriends, and a Mystery Man

Lindsay Hubbard, whose dating history is being explored following her pregnancy announcement
Photo Credit: Felix Kunze/Bravo via Getty Images

The OG of Summer House and Queen of the Hamptons has to go to my girl, Lindsay Hubbard. She is strong, demanding, and assertive. Most of the time, these are not bad traits, but every so often, the PR guru gets a bit too activated and lets out a roar that a lion would be scared of.

Even though I love Lindsay, it doesn’t seem like the men she has dated have much respect for her. That is, until now.

So, let’s take a deep dive into Lindsay Hubbard’s dating history, past boyfriends, and where she stands today…

Summer House Season 1 – When Lindsay Hubbard dated Everett Weston

Lindsay Hubbard, who dated Everett Weston during Summer House Season 1
Photo Credit: Charles Sykes/Bravo

Season 1 introduced us to the Lindsay and Everett Weston era, which honestly was pretty cute until it wasn’t. Everett had served in the Army for five years, which had resulted in some psychological trauma and post-traumatic stress disorder.

Lindsay gushed to the cameras during the series premiere, “​Everett and I have been friends with this group for over two years, but we only started dating two months ago.” Even though Lindsay hoped to walk down the aisle, the duo had major disagreements. 

Season 2 of Summer House showed Lindsay as single as she shared, “Of course I miss Everett, but this year, I’m single f*cking Lindsay, and I’m going to have my own room to do whatever the f*ck I want with whatever guy I want.” And thus began Lindsay’s adventure in love or lack thereof. 

Summer House Season 4 – When Lindsay Hubbard dated Stephen “Stravy” Traversie 

By Season 4, Lindsay had grown tired of her single jaunts and found a new man to drive crazy, Stephen Traversie, but not before testing the waters with Carl Radke. At the time, the two decided to stay friends after shots of Fireball couldn’t ignite their passions.

Stephen seemed chill, but Season 5 showed the couple at their all-time low. What followed was a grim Excel PowerPoint about why their love worked and the iconic line “How many sandwiches have you made for me?”

Even though the couple broke up after Stravy realized he wasn’t going to get a word in edgewise, he returned to Montauk in an attempt to perform a grand gesture, which included planning a romantic dinner outside under the stars. But it wasn’t enough, as both decided they were better off alone. 

Winter House – When Lindsay Hubbard got flirty with Austen Kroll

Austen Kroll, who wasn't dating Lindsay Hubbard, but did enjoy a kiss with her
Photo Credit: Charles Sykes/Bravo

As we all know, Austen Kroll is the Honda Civic of men, so I’ll never understand why so many beautifully smart Bravo women are attracted to him. Yet Lindsay evidently fell hard for this snake oil salesman even though the Southern Charm playboy apparently felt nothing for her.

During Season 1 of Winter House, fans got an up-close personal look at Lindsay’s flirting techniques, which seemed to work like a charm on Austen. Stowe, VT, showed the duo going on dates, flirting by the fire, and sneaking off into their bedrooms at night. 

Even though Lindsay shared that she “loved” him, Austen filleted her heart as he answered that he only liked her “like a sister.” But brothers and sisters don’t hook up, right? However, Austen the cad did what he does best and turned his sights onto Ciara Miller.

Speed forward to Summer House Season 6, which showed Austen and Lindsay sharing a smooch. Honestly, their tryst was confusing AF! 

Winter House Season 1 – When Lindsay Hubbard dated Jason Cameron

Jason Cameron, who was dating Lindsay Hubbard during Winter House Season 1
Photo Credit: Greg Doherty/Bravo

During the same Winter House season, Lindsay turned her eyes to Jason Cameron, a pretty put-together model from the Big Apple. Both didn’t believe their romance was just a vacation fling and tried to have a relationship outside the show.

As viewers learned, Lindsay ended up getting pregnant and having a miscarriage, causing the two to drift apart. A sad story on the relationship history timeline.

Summer House Season 6 – When Lindsay Hubbard started dating Carl Radke

Carl Radke and Lindsay Hubbard during Summer House Season 8, when they were still dating
Photo Credit: Clifton Prescod/Bravo

I am no Negative Nancy, but I just never felt that Carl and Lindsay were soulmates. I think they made the perfect PR couple, but somewhere along the lines, the agreement didn’t work anymore.

The two were polar opposites as Lindsay liked to party, and Carl was sober living. Between moving in together and isolating year-long friendships, the couple was toxic, and Carl called off the wedding in May 2023. Lindsay claimed to be “blindsided” by the entire thing, but viewers weren’t convinced after watching Season 8 in its entirety.

Lindsay Hubbard now has a mystery boyfriend and baby daddy

Now, Lindsay is keeping her dating life private. She’s pregnant to her mystery boyfriend, and only minimal details have been given. He, apparently, doesn’t like the spotlight. He’s also never watched Summer House. What we do know, however, is that he’s a doctor who works in “biotech investing,” according to People. Get it, Linds!