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Move Over Carrie Bradshaw: Meet Brynn Whitfield, NYC’s Ultimate Relationship Guru

For the girls who dreamed of living in New York or were lucky enough to be single in the best city in the world, there’s an obvious connection between Bravo’s betchiest franchise, The Real Housewives of New York, and HBO’s Diary of Mad White Woman, otherwise known as Sex and And The City. Being awarded an apple by Andy Cohen comes with some big navy blue Manolo Blahniks to fill; and RHONY reboot rookie Brynn Whitfield has done exactly that. Like Holly Golightly, Brynn effortlessly bounced from the glamorous (blowouts and luxury cars) to the emotionally raw (a mixed-race family history she’s still learning about every day and the loss of her grandmother). The way Brynn discusses love, on the show and in our one-on-one conversation, is wildly refreshing: Dating doesn’t have to be complicated — but it is interesting.



Her credentials? Brynn has lived in LA and New York and “could write volumes upon volumes about dating stories, dating dreams, and dating nightmares. It’s kind of something that [she] learned from trial and error.” Brynn was also a student of LA radio legend Pat Allen, an old-school relationship coach who preached yin-yang energy from The Tao of Dating. I was thrilled to get some dating advice from Brynn Whitfield, the free-spirited Housewife with an honorary doctorate in falling love. We chatted about the six-month theory, what makes the perfect man, the 10-year itch, and one scalding hot SATC take. This is for science and for the girls, duh.

What Is the Six-Month Theory In Dating?

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With Peter Pan syndrome on the rise among men nationwide (proven by a study independently run by me and my group chat), it’s fair to wonder: When will a man be ready to settle down in 2024? Brynn tells me she feels there’s a simple answer. Since “men are pretty freaking straightforward. They don’t overthink… They call you when they want to have dinner with you. They don’t care if you’re with someone. They don’t care if they have to fly to a different country” (a true story from Brynn’s dating arsenal), Brynn “strongly [believes] that they know very soon.” A man will know if he wants to marry you in six months or less, to be exact, according to Brynn. But remain calm: Just because they know they would marry you, doesn’t mean they’re going to instantly “act on that intuition, that it’s going to be happily ever after, and they’re going to commit to you.”



As someone who has been engaged multiple times before, Brynn stands firm on this theory. In fact, she’s “been proposed to way more times than [she’s] been engaged,” and feels fortunate to have gotten so many rings, despite calling those relationships off. I mean, more diamonds can never be a bad thing, right? Brynn concedes “Obviously I’m not skilled at getting down the aisle. But this other stuff I’m like a freaking expert at.”

Even scientists agree with her six-month theory. A study of 2,000 single and married people conducted by the Proceedings of the National Academy of Sciences of the United States of America found that married people thought it took 172 days AKA about six months to be sure they found the right person. Single people, on the other hand, projected it would take them at least seven months or longer to make up their minds. So basically, when you’re on the sidelines, the decision seems huge, but for those with the right partner, making up their minds came easily. Data also found that it takes five negative interactions to decide that you’re incompatible with someone (I guess three strikes and you’re out is only for baseball) and that the honeymoon period naturally comes to an end after month three.



So, how can a girl test if he’s in or out at the six-month mark? For that, Brynn follows an age-old adage her grandmother used to tell her: “Actions speak louder than words.” If he’s saying you’re the one, but you don’t feel like it’s genuine, that’s probably the case. When it comes to dealing with flaky men (or her Housewives co-stars) Brynn thinks that “people actually mean some of the bullshit that comes out of their mouths. They intend on doing it, or they want to believe that they’re that person. But at the end of the day, their actions speak for themselves.”

Brynn Whitfield’s Dating Rules

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Brynn shared a few tips she’s gathered from her personal experience as a straight woman pursuing straight men. While age doesn’t specifically matter, if someone “is not mentally stimulating you” you should be asking yourself, “Why am I with someone who isn’t on my same emotional or mental playing field?”



She stands by the three-date rule, because “the first one, you can be way too horny for them — maybe you have drunk goggles on.” On the other hand, nitpicking can get in the way like when “you left the date and you’re like, I don’t know. I don’t if I like the way he held his bread.” Pat Allen taught Brynn if someone matches at least 51% of your dating criteria you should give it a real shot “because realistically, no one’s going to ever be a hundred percent.”

How do you identify and rank your dealbreakers? Brynn recommends getting a little nerdy with it. She enlightened me about an experiment conducted by a quantitative futurist (yes that’s a real job title) named Amy Webb, featured on NPR’s TED Radio Hour. After another disappointing breakup, Amy identified 72 compatibility data points and used them to create a scoring system to “mathematically calculate whether or not I thought the guy that I found online would be a match.” Those from the sample pool who scored over 900 points would receive a date, and only a man above 1,500 points would be worthy of a relationship. She called it “grocery shopping for a soulmate” and concluded finding love is a numbers game that’s a lot easier when you know what you want.



More than anything Brynn believes women should “just relax” and give yourself a chance to find out if you like the guy after the first date. “I fall in love all the time,” Brynn told me. In a time when it feels like the world is one of those wieners spinning around the rotisserie oven at Costco, it feels nice to hope maybe Brynn’s lovergirl status could become infectious.

How does the “10 Year Itch” work for single girls?

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The 10 year itch is another relationship theory that suggests 10 years into a marriage you might find yourself waking up next to someone you feel like you have nothing in common with anymore.

Brynn can see a huge change in her relationship with dating now compared to when she was in her 20s. “Expectations can be the early death for a lot of relationships, and I think I had dumb expectations. I’m just such a different person. I always laugh. Had I gotten married any of those times, I’d be on my third divorce by now for sure.” With all the hours she was clocking into her professional life, it was easy to fall into being an “emotional hot mess” who “was projecting a lot.” Now Brynn is confident she’s done the work to be a great partner which has ironically enough allowed her to stop “rushing and jumping from one relationship to another,” because she knows how to have fun all by herself.



What kind of Prince Charming could lure Brynn from her Arch Digest-approved castle? If it’s not obvious by now, Brynn is a sapiosexual (someone who is turned on intelligence). So while she’s dated plenty of professional athletes and 6’5″ blue-eyed finance guys, her strong connections have been with men who are leaders in the tech and economics industries (“two of them of were actual scientists”) because she “fell in love with their brain.” As for dating someone in reality TV, Brynn would take an “under the radar” businessman any day.

Who Are Brynn Whitfield’s Relationship Icons?

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There are far more breakups than makeups on Bravo these days, but there is one Bravoleb couple who has Brynn’s heart: “Katie and Ariana, their friendship is so perfect, that true friendship. You stick with your friends. And to me, my friendships are just as valid, if not more so, as my romantic relationship.”



Naturally, we couldn’t end our chat without sharing thoughts about the OG of hopeless romanticism in The Big Apple, Carrie Bradshaw (we’re all a little bit more Carrie than we’d like to admit, just accept it). Like for me and romcom-addicted girlies everywhere, SATC is canon for Brynn. Her unpopular opinion wasn’t about Carrie and Big or even Carrie and Aidan (who we both agreed should’ve never taken Carrie back). Brynn, the brave soul she is, told me she rooted for Charlotte and Trey to stay together: “I thought it was her dream. I’m all about fairytales, and I think I wanted Charlotte to have hers.” Brynn can already hear you screaming through your phone, don’t worry! But when she told me “I know the message is that fairytales don’t exist, but I think for me personally, I’m still waiting for my fairytale, so I will sit and wait,” I honestly couldn’t help but agree.