Fake Dating a Billionaire
Today’s newsletter has been hijacked by Pollyanna “Pip” Fletcher who is “fake dating” the heir to a greeting card empire.
Darling reader,
Let me tell you something that overpriced reality shows, Pinterest boards, and Cosmo quizzes never will:
✨ Fake dating a billionaire is not the vibe. ✨
I know, I know — sounds fabulous, right? Designer dresses. Flashbulbs. A sexy man who has “a staff.” There’s money. There’s mystery. There’s someone saying “We’ll handle it” when everything goes to hell.
But here’s what they don’t print on the invitation …
…sometimes the billionaire in question is a six-foot headache with a DJ playlist for a personality and the emotional maturity of a pubescent possum.
And no — you can’t quote me on that. But you can call him Snickers.
He’s the high-gloss Band-Aid slapped across Woodward & Co.’s carefully crumbling dynasty.
And smack dab in the middle of it was a girl named Pip who simply wanted to sell vintage frocks and keep her dignity intact.
She never stood a chance.
Step One: The “Date”
The first time we rolled Pip into the PR war room, she looked like Bambi at Bergdorf’s.
And he — the international man-child formerly known as Sheldon Woodward III — was in his usual uniform: sunglasses indoors, three-day stubble, and zero regard for anything.
Kit (our PR queen and chaos wrangler) had already drafted Tweets, contract clauses, and a pet adoption plan before the fake couple had said more than three words to each other.
One of those words, by the way, was “Piglet.” He’s a French bulldog. Obnoxiously photogenic.
The “love story” rollout began, and so did the breakdown of Pip’s sanity.
Step Two: The Smile
There’s this thing that happens when you’re pretending to adore someone in flats you didn’t pick, for a cause you only sort of believe in.
You start asking questions you don’t want the answers to.
→ Like why he knows her coffee order now.
→ Or why she flinched when someone joked about their “engagement.”
→ Or why their eye contact is suddenly a little too long.
And gods help me, I know that look—when fake starts melting into something altogether less manageable.
Step Three: The Spiral
Here’s what they won’t admit but I will: billionaires are exhausting.
They’re used to being catered to, adored, and lightly scolded on camera — never called out in private.
Snickers may be beautiful, but he’s a feral peacock with abandonment issues and a club residency. And Pip? Poor thing. She had every plan to take the check, save her aunt’s gallery, and ghost us all.
Instead, she started folding his t-shirts. Voluntarily. Color coded.
The worst part?
He started folding hers back.
So, why YOU should avoid fake-dating a billionaire?
• Because the gig pays in stress wrinkles and silent sobs in marble bathrooms.
• Because falling (even a little) feels like failure.
• Because every joke, touch, or quote-unquote moment is up for public consumption.
• Because the only private part of your relationship is the part you never speak out loud:
“What if I want this to be real?”
And if that thought ever crosses your mind, my love — run. Or charge extra.
Final Thoughts From the Bix Booth
As someone who has staged a wedding, dodged three NDAs, and bribed a dog groomer for comment control, here’s my best advice:
Don’t fake-date a billionaire unless you’re ready to lose your grip on the script.
They charm. They push. They buy your favorite cake and then look confused when you cry.
And sometimes, they kiss you like no one else ever has — and ruin you for sane men forever.
So let me be your cautionary tale. Or don’t.
Who am I to judge?
Just don’t say I didn’t warn you.
xoxo,
Pip
Grab the Billionaire’s Naughty Secret Today
👑 Want the full tea? Billionaire’s Naughty Secret has the whole glorious disaster, steamy DJ banter, fake fiancé chaos, and one very flatulent Frenchie. You’re gonna love it. Probably.
