Confessions / Lit / Love / Sex & Love / Society & Culture

Single Women In Their 30s: The Real Deal

shapeimage_2 shapeimage_3By Jill Di Donato

New Year’s Day. I wake up in the guest room of my best friend Frankie’s house. Let me tell you about Frankie. She’s a successful entrepreneur with a town house in the exclusive Brooklyn neighborhood called The Heights — you know, where the Cosby show was filmed during the 1980s.

She’s gorgeous, a pioneer in her field — who often speaks at “women in business” conferences, has a closet filled of designer clothing, walls lined with Kiki Smiths, a body you can bounce a quarter off of, oh, and, like me, she’s single.

Last night, also known as single gal’s hell, New Year’s Eve, we resolved not to go home with any losers, not to get hammered because we were without boyfriends at a party where everyone was coupled up, and not to fill our faces with the decadent spread of highly caloric indulgences that would only leave us feeling fat, yet empty.

Instead, we applied fierce cat eye make-up on each other, drank just enough champagne to give us a nice buzz, boogied with decent rhythm to Xbox’s Just Dance Hip-Hop, prank called ex-boyfriends who were particularly rotten to us over the past year, and perused Grindr for hot, yet totally unavailable men.

Did I mention we’re in our 30s? Lest you think we took a time machine back to our high school days, (Lord knows I wouldn’t want to go back there, even if my skin had that fresh glow I spend hundreds to recreate, and my stomach was naturally concave) we’re a new breed of single women: successful, driven, ambitious, educated, and playful. Though we have different beliefs about what it means to be single, both Frankie and me agree on one thing: we much rather have fun with ourselves than settle for being with some uninteresting guy who’s just a warm body.

I mean, now that we’re in our 30s, the idea of settling is hard to swallow, and as women in our 30s, we have a comfortable relationship with being alone. We’ve been rejected, been through heartache, have loved and lost and HAVE SURVIVED. Our moms are always telling us that we’re a new generation of women — women who “do things differently,” and live lives that they only dreamt of. I wonder, is this a backhanded compliment, or am I being overly sensitive because I’m not 100% on board with how we “do things differently?”

Yes, Frankie and I lead amazing lives. We have the opportunities to meet new people, have exciting sex, and share stories that entertain each other. But is that enough? Are we happy? Are we, as women of this new generation — a generation where we have more choice over the roles we can inhabit than our mothers — are we fulfilled enough? I have to say, sometimes yes, sometimes no.

As I mentally scan last night’s escapades, I tell myself, we are confident enough in who we are that we don’t have to discuss economic exit strategies or the latest issue of The New Yorker (which we do on occasion; we’re not vapid women) to prove how accomplished and great we are. Still, crank calls are not the stuff grown, successful women are made of. I can’t help but wonder, sometimes, in reaction to not being married, coupled, or non-single, we inadvertently revert to adolescent behavior because our teens or even early 20s were a time when it was permissible to be unattached. As confident as we are in ourselves, are we ashamed of being alone? I shudder at the thought.

Or, that is, I did until last night.

“Were you serious about that 52 week commitment to being single?” Frankie says as she types in our breakfast order on a website that will deliver exactly what we want. “I mean Jill, can you afford to waste that time?”

I repeat my theory on being ambiguously single, and insist my declaration was not in fact a side effect of New Year’s Eve neurosis.

“It’s the exact opposite of wasting time. I’ve been wasting time by being ambiguously single. Until I can figure out exactly what I want, I’m going to embrace my single-dom. I’m going to do everything I can imagine as a single gal in New York, not giving a …” Frankie stops me, laughs, and adjusts the glasses she wears only during these private pre-breakfast conversations. “And to think of you last New Year’s Day. I don’t exactly have a handle on you now, but I like you a lot better than the Jill of the Jill and Lower-Than-Whale-Shit disaster.”

52 Weeks of Sex

52 Weeks of Sex

Lower-Than-Whale-Shit. Let me explain: that’s the name Frankie coined for the ex who devastated my life. We all have one of these: men who sneak their ways into our beds, hearts, wallets, homes, and leave us a pile of mush when they just as quickly disappear, forever, or until we run into them when least expected. Which of course, always happens.

Yes, last New Year’s Day I was a sight for sorry eyes. Mine were swollen from crying so hard they could barely open.

There I was: left, devastated that the six year romance I thought would culminate with a walk down the aisle, was a mere illusion I gave my life to, while everyone around me, including Frankie, knew it would bring me nothing but trouble.

He cheated; he lied; he promised to love me better; he gave his word he would reform. We went to couples’ counseling; we talked to my mother; we talked to his mother; we talked to each other until we could talk no more. But in the end, it didn’t make sense. We both knew it — still — I couldn’t bring myself to admit it.

And so he picked New Year’s Eve of last year to vanish from my life forever, with a text message letting me know that this was the final fight; we were done; he wasn’t coming home; our home that had once existed was no longer our home; I was now alone. I could say from this experience that men lack a “sensitivity chip” when it comes to timing. And yes, my year was pretty much a living hell. I moved into Frankie’s guest room and spent most days feeling defeated.

A typical Tuesday went something like this:
Frankie: “Aren’t you going to get off the couch?”Me: “Law & Order SVU Marathon.” (For some reason, during my post-break-up depression, I couldn’t get enough of watching violence inflicted upon women.)Frankie: “So, you’re canceling your classes to just lie here?”Me: “Yes.”

Frankie:  “Can you please shower by the time I come home. I can smell you from here.”Me: “Shut up. I’m missing the beginning.”

Frankie: (shaking her head and packing her handbag with the day’s necessities): “A woman gets hurt, violated, maimed; what else do you need to know?”

In times like these –post- break-up– you learn who your real friends are. Those women who will tolerate you when all you want to do is wallow in your aloneness and go over every last detail of the failed relationship like you’re breaking down the Da Vinci Code. The patience Frankie had to be my friend, let alone let me live in her house; damn, I owe this woman. BIG TIME.

I guess that’s what single women in their 30s do for each other — they become each other’s rocks.

For one whole year, I crashed in Frankie’s guest room. During this year, I was miserable. I lost ten pounds. This weight loss didn’t suit me. I hardly laughed at all during this year. I dated a couple times, but only ended up comparing the dates to my failed relationship and ended up feeling like a total loser. It was a no-win situation. I annoyed my friends. I almost lost my job. I lost a ton of money on what had previously been “our home.” I irritated myself with my very own pathetic-ness.

But I made it through. Made it through a year well-enough to muster the artful craft of cat eyes and crank calls — made it through to know: enough is e-fucking-nough.

“So you’re really going to just be the single gal, no commitment wanted? Wouldn’t you be better off dating online?” Frankie finished typing in our breakfast order and readjusted her glasses.

“You would say that; you run a website.”

What I didn’t say to Frankie was that she spent an entire year dating online and was still single. Of course, in her mind, she was playing a “numbers game,” and with enough bad dates under her belt, she was bound to score not just a good date, but a great man.

But I couldn’t help think that everything we’ve been taught about men and dating wasn’t adding up to anything real. I’d just spent a year not trying at all, and Frankie spent a year trying like hell to find a mate, and here we both were dancing choreographed routines to 90s hip-hop on New Year’s Eve.

Not to sound like a total narcissist, but we are good deals — great deals — when it comes to the “whole package” a man supposedly wants. Were we too picky? Too hung up on ourselves to really and truly open up to someone? Or were we just playing with an outdated set of rules that didn’t suit our lifestyles and sense of identity.

The above is an excerpt from Di Donato’s forthcoming dating book, 52 Weeks of Sex: Diary of A Single Gal.
Jill Di Donato holds an MFA from Columbia University, where she’s also taught writing. Her debut novel ‘Beautiful Garbage‘ published by She Writes Press is available on Amazon. Currently, she is an adjunct professor of English at the Fashion Institute of Technology and teaches at Barnard College. Di Donato has appeared as a sexpert on several radio and TV programs and is at work on a nonfiction book called ‘52 Weeks of Sex: Diary of a Single Gal.’ You can visit her website at and follow her on Instagram at @jddoe

Images: Jill Di Donato


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