Lindsay Hubbard’s Dating History: Boyfriends, a Fiancé, and No More Bravolebs

Lindsay Hubbard
Photo by: 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. But even though I love Lindsay, it doesn’t seem like the men she has dated have much respect for her. So, let’s take a deep dive into her dating past, just for sh*ts and giggles.

Summer House Season 1 – The Everett Weston Era

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 – Get Lindsay a Sandwich, 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) is Coming – Austen Kroll

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? But Austen, the cad, did what he does best and turned his sights onto Ciara Miller, forever solidifying that those two women would never be friends. 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 – Jason Cameron

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.

Summer House Season 6 – Carl Radke

I am no Negative Nancy, but I just never felt that Carl and Lindsay were soul mates. 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.

Summer House Season 8 – SINGLE

Hot Hubbs Summer is back, and I think it is here to stay for the foreseeable future since Lindsay is now back on the market. Summer House fans watched in real-time as Lindsay started picking up the pieces of her life, and she isn’t doing to shabby. She recently bought a home in Nashville and is working on figuring out what she wants out of life. One thing is for sure: She won’t be dating any Bravo men in the future, and most likely, she won’t be waiting around for someone to make her sandwich.


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