RSBB #1: The time I decided to hire an escort

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Dec 10, 2024

What is RSBB?

In last week’s Cocoon I wrote about curtsies and war dances and my decision to start sharing the tales and takeaways from my forays into mid-40s, post-divorce, perimenopausal, red-state dating.

I have a name for this new weekly edition, but it’s a little spicy, so I’m referring to it by its initials RSBB above the paywall. RSBB will officially launch in January, but today I’m sharing a preview for anyone who’s on the fence. Keep reading for a free sample of what you can expect. My goal is that at least 100 of you will join me by January 31, and I hope you’re one of them.

What’s staying the same?

The Cocoon in its current, free form will continue to land in your inbox on the first Tuesday of every month with an essay about transformation for an educator audience (broadly speaking) as well as quick hits about what I’ve been seeing and thinking about in my recent work with schools, teachers, and leaders, what I’ve been doing and experiencing on my field trips, and what I’ve been reading and ruminating about.

What’s coming in January for paid subscribers?

A weekly edition every Tuesday (except the first week of the month when the free monthly edition comes out).
Absurd stories, cautionary tales, funny-sad aha moments, so-it-was-patriarchy-all-along revelations, and lessons gleaned from my experiences being single for the first time since 2006.
A community–necessary now even more than ever, I believe–for anyone heading into their second act, pressing the reset button, or determined to live the next half very differently from the first.

FAQs:

Q: What does your dating life have to do with the education stuff you normally write about?

A: I write about transformation. Publicly, I mostly write about learning as a transformational experience for both students and adults, and what I’ve learned from more than two decades in education as a classroom teacher, instructional and leadership coach, professional development facilitator, educational consultant, and co-author of a book about preventing and addressing educator burnout.

For the past two years I’ve been on a (mostly) private journey of transformation in my personal life too: my 17-year relationship ended suddenly, I moved home to Miami after 22 years in New York City, and I started dating again in a vastly different landscape from the desktop-Match.com era of my 20s.

The Cocoon is a community that inspires and holds space for transformation, and I know there are a lot of other people seeking a sense of community, especially right now. Because vulnerability fosters trust and connection, I’m going to share some really vulnerable moments.

As with my book about educator burnout and my essay about infertility and endometriosis, I write what I needed to read when I was in crisis–in this case, when I feared I’d be alone forever. I write for the past me whose life tilted sideways. To paraphrase Julia Cameron, I write to right myself.

I also write out of my experiences as a cis straight white woman. I have blind spots, and I welcome feedback about how to make this an inclusive, accessible, and welcoming space for everyone who wants to be here.

Q: You are my coach/colleague/mentor/neighbor/family. Do I really want to read about your dating life?

A: Here are some reasons why that answer might be yes and also how to get to yes if you’re currently more like maybe/don’t know/not sure:

You want more–more Cocoon, more war dance disguised as curtsy, more about the pleasures and politics of being single for the first time since the George W. Bush administration.
You want to support and amplify women’s voices and experiences.
You’re looking for a likeminded community to combat your sense of despair/isolation/terror in these times.
You’re single, newly or not, and trying to figure out who you are if you’re not a spouse/partner/other half.
You don’t want to date the same way this time around.
You’re curious about ethical non-monogamy and polyamory and open relationships (and also would like to know the difference between them).
You have experienced unspeakable, existential betrayal and are trying to figure out how to intimately trust another person again.
You’re curious about how someone whose marriage ended in pyrotechnic infidelity navigates non-monogamy.
You suspect that at least some of what you were taught about dating, sex, relationships, and marriage was a total lie.
You’re curious about what it’s really like to be a childless cat lady (in spirit; I’m not a pet person).
You fear you’re a bad feminist because you worry about the aesthetics of aging but wish you didn’t.
You love Florida Man memes and are dying to know what it’s like to date them.
You could use a laugh or two on Tuesday mornings.
You’re looking for a gift idea for someone else to whom one or more of these apply.

Q: How detailed are you going to be? What if I want to subscribe but don’t want to hear all the, um, specifics?

A: I’ve got more than a year’s worth of story ideas so far, and none of them requires intimate details. I have plenty to say while keeping the bedroom door closed. If I ever feel like I need to share something that’s a little more open-door I’ll include a note at the top of the post so you can decide if you want to keep reading or not. I’ve also included some examples of what you can expect below.

Q: I identify as a man. Is this for me?

A: Very much so.

Have another question about RSBB?

RSBB #1: The Time I Decided to Hire an Escort

I did not say it aloud until the day after my marriage collapsed, but the idea of hiring an escort if I was ever single again had been there for awhile. It was something I knew without knowing how I knew it.

Something else I knew without knowing how I knew it: my marriage was over before it ended. I suspected but could neither prove nor fully believe it. Not yet. But sometimes I thought about what it would be like to be single again. I would be free to do whatever I wanted.

However, I would also be a middle-aged woman with wrinkles, gray roots, stretch marks, sun spots, cellulite, and a perimeno-tummy. I assumed no one desirable was going to desire me. What good was it to be free to do whatever I wanted if there was no one who wanted to do it with me?

Fortunately, I was pretty sure I could hire someone. Certainly there was a desirable man who would want to be with me if I paid him. If I’d learned anything from 22 years in New York and a lifetime of capitalism it was that you could have anything you wanted if you were willing and able to pay for it.

I saw another benefit of making this a business transaction. I hadn’t been single since 2006, which was before smartphones, dating apps, #MeToo, and ubiquitous polycules. I didn’t really know how dating worked anymore, but I knew that if I was single again my experience would be very different from when I was in my 20s and not just because the world was different. I was different, too. Some of the things I’d shrugged off or gone along with back then nauseated me now. I didn’t want to feel coerced or pressured or guilted into things I didn’t want to do. I was starting to figure out what I did want (more on this in the future), and I was pretty sure the best way to get it was to have a greater sense of agency, which I believed I’d have as a paying customer (another life lesson from late-stage capitalism).

Ergo, if I was ever single again I would hire an escort, preferably someone like Channing Tatum as Magic Mike (granted, a stripper, not an escort).

When I actually did find myself suddenly single, it was late afternoon on a Sunday in January 2023. By 7pm my marriage was swiftly and incontrovertibly finished. We would not be going to couples therapy this time.

My sister was on the first flight from Miami the next morning, and Monday was a jumble of appointments, phone calls, and subway crying. By 4pm we’d finished everything on my to-do list and found ourselves in Soho. We sank into a semicircular booth in a deserted restaurant, and my sister ordered everything that sounded good, but I had no appetite for chickpea fritters or whipped ricotta. Instead I drank my first Coca-Cola in years. I hadn’t slept in 36 hours and was delirious with exhaustion and disbelief.

I was crying and laughing and talking too loud, pontificating about all the things I’d never have to do again (endure snoring and the NFL, share a bathroom, perform a certain sex act).

“As soon as I’m ready I’m hiring an escort,” I announced to my sister and half the wait staff, “a beautiful man with a beautiful body who knows what he’s doing and doesn’t expect anything from me.”

My sister stopped laughing and stared at me. Maybe I had gone too far. Maybe she was going to point out that I shouldn’t objectify men if I didn’t want them objectifying me. Maybe, after a lifetime of insisting there was no such thing as TMI between us, I had finally said too much.

Then she leaned forward, put her hand on my arm, and looked me in the eye.

“You don’t have to pay for that,” she said.

And like so many other times before, since, and surely for as long as we’re both alive, my sister was absolutely right.

Thanks for reading The Cocoon by Rebekah Shoaf! This post is public so feel free to share it.

Thanks for reading this free sample of RSBB

If you become a paid subscriber, starting in January you can look forward to future posts about picking my dating app, receiving an indecent proposal, dating an anti-vaxxer, dumping a non-voter, making dental health a non-negotiable in potential suitors, and more.

Bonus: If you become a paid subscriber by December 31–for yourself or as a gift for someone else–you’ll also receive a guide to my New Year’s routine including how I reflect on the year that’s ending, set intentions for the year that’s beginning, and use commitment instead of accountability to keep myself on track all year long.

And for those of you who have already subscribed, thank you for being one of the first supporters of RSBB. You’ll find out what that stands for in issue #2, coming January 14.