Brynn Whitfield's Dating History and Other Updates on Her Love Life

In July 2023, Brynn confirmed her “single” relationship status to The Daily Dish at RHONY Season 14 premiere event. "I am single. I feel so lame, I’m like I should have got a boyfriend for this red carpet! I am single, though," she said, adding, "Still hanging out with like, two exes."

Brynn had no trouble poking fun at her relationship status, posting a picture of herself on her Instagram in October 2019 with the caption, “It’s all about that sweet, innocent, first date look. A look that says: if you act up, I will marry your dad, become your stepmom and make your bedtime 7 p.m.”

Brynn opened up to the 'Wives about her complicated romantic past while at Erin Lichy's home in Sag Harbor in The Hamptons in Season 14, Episode 3. She revealed that she had previously been engaged three times, including to Gideon Lang-Laddie, who had appeared on RHONY Season 14 as Brynn’s friend. 

Brynn also shared the deeply personal reason why she ends up calling some of her exes back from time to time.

"I'm not close with any of my relatives, and I so badly want to have a family of my own, and traditions, and a place to go," Brynn said in her confessional during the episode. "So, there's times when I'll call up some ex, and be like, 'What are you doing?' You know, it's Band Aids. It's painful. It's hard."

Gideon is Brynn’s third ex-fiancé. He was born and raised in London and worked on Wall Street in finance for over 20 years before joining Mauricio Umansky’s real-estate firm, The Agency, as an agent, according to The Agency website. 

He is a graduate of the Royal Agricultural University, Cirencester and moved to Beverly Hills in 2015. Among his long list of hobbies: He’s a passionate amateur polo player who trains annually in Argentina; a classic car collector; a fencer; a fly fisherman; and a wine enthusiast. He also founded the Prostate1000 charity in 2009, which raises funds and awareness for prostate cancer research. 

Brynn and Gideon spent five years together as a couple after meeting through the Tinder dating app. Bravo fans got to meet Gideon in RHONY Season 14, Episode 7, when the classic car collector invited Brynn to join him in shopping for his next whip. 

“He’s literally a Prince Charming,” Brynn said in the episode. “I didn’t open a door for five years. I didn’t pick up one tab. I can’t even stand up at a dinner table without him jumping up.” She recalled Gideon’s grand wedding proposal outside the Ritz-Carlton during sunset, with The Proclaimers’ “I’m Gonna Be (500 Miles)” playing and Brynn’s dog in attendance. 

Ultimately, though, Brynn recalled panicking and calling off the engagement. “I see myself as little Brynn with the little afro, like, I didn’t see myself as someone’s wife,” she said. “I wasn’t ready.”

Still, there seems to be a bit of hope that the spark might reignite in the future. “I feel like the chances are now 25% [that] we might end up together,” Brynn quipped of Gideon during an August 2023 episode of Watch What Happens Live with Andy Cohen. “It’s a bear market.”

During a September 2023 episode of WWHL, Brynn revealed that she had a bit of a crush on Shep. "It takes one commitment-phobe to know another commitment-phobe, right?" she joked to Andy Cohen at the time. "I like Southern Charm. I’m from Indiana, so Midwest and the down South, we play dirty."

Though Brynn and Shep exchanged DMs, it wasn’t until BravoCon in November 2023 that the two met in person in Las Vegas. Shep and Brynn had drinks together in Vegas, but Brynn ultimately “went home” while Shep decided to go out. Shep recounted their meeting during a panel on November 5, saying, "I met Brynn yesterday. I like her. I like her! She's cool."

However, it seemed like romance wasn’t exactly in the cards for this Bravo pairing. "I think we're really good friends,” Brynn shared at the “Dynamic Duos” panel after Andy asked if his attempts to set the two up had "gone by the wayside."

"Why?" Shep quipped at the panel. "What did I do?!"

During the “It’s Ladies Night” panel, Andy also revealed that Shep had previously spoken to him about feeling a connection with Brynn. “He came over to me before The Bravos,” Andy said. “He was, like, ‘I am stunned by Brynn. She’s so beautiful. She's so tall.' He goes, ‘She's really smart … she’s a star.’”

On RHONY, Brynn never held back her flirty personality, and even seemed to take a bit of interest in her cast mate Jenna during Season 14. During the Season 14 reunion, though, Jenna revealed that she didn’t think Brynn was being serious when it came to her flirtations, and at BravoCon 2023, Brynn shared further insight. 

“I’m ready to go to City Hall,” she quipped at the “Let’s Hear It for (New) New York” panel during the Las Vegas event, before adding: "I have to be respectful because she's in a relationship [with photographer Cass Bird], but if I wanted to disrespect her relationship — she's a hot babe. She has everything I want. Like, I'm 37... beggars can't be choosers. I want to have kids, I want it. You know she's got everything. She's got the chic loft. She's got the looks ... I could be the cool stepmom. [Her son] doesn't hate me, he loves me."

Before she was officially part of the Bravoverse as a RHONY cast member, Brynn had a bit of an encounter with the SUR manager. On an August 2023 episode of WWHL, Brynn revealed she had “been there, done that” with Peter. 

“I was in my 20s,” she added, after Andy said he knew the two had made out in the past.

During RHONY Season 14, Episode 3, Brynn also teased another romance in her past, this one with an NFL player. During a game of “Two Truths and a Lie,” she claimed she “reverse cowgirled” two of three men: a professional athlete, a Saudi prince, and a governor.

The governor, it was later revealed, was the lie. 

Although Brynn wouldn’t reveal the name of the pro athlete she hooked up with, she did divulge that he was “a Super Bowl winner.”