Dating is Not a Bitch When You’re Not Dating

Welcome back! It’s been four years. FOUR. I believe (re)introductions are in order:

Hi, I’m Sienna — the author of this blog and the hopeless yet snarky romantic who’s not ready to give up on finding love, despite the fact that I am increasingly on AARP’s hit, er, marketing list, and I recently attended an online support group for women with menopause questions. (Turns out you can get pregnant after 45 if you still have a period. Use a condom.)

It’s been four years since my last entry here. Four years since I met the charming winemaker who was actually a goat in human clothing (see “Do You Wanna Bang in a Barn?”). Four years since I abruptly decided, “Dating is such a bitch that I don’t want to do it anymore.” And so I stopped.

That would explain my absence. Apologies if my disappearance and lack of storytelling about my f-ed up dating foibles stripped you of some comic relief—something we all needed, especially through the worst of covid.

One, I did have covid, and I had the long-haul version, so meeting a man without an “MD” behind their name wasn’t even a thought—I was only focused on seeing the ones in the white jackets who could help me get better. And two, how the fuck do you even date during a global pandemic? I’m so, SO over texting back and forth a million times; FaceTime and Zoom are only good options once you’re in a relationship; and, perhaps most importantly, my wardrobe slowly morphed into a compilation of black leggings, matching jogger sets, oversized sweatshirts and too-small sports bras. Staring at my closet and complaining that “I have nothing to wear” became a much more typical Saturday evening activity than trying to force a sexy outfit together and act like I cared about meeting someone without a stethoscope or prescription pad.

P.S. What are shoes, even? Where the hell did I put my makeup in 2020 and has it expired by now? Did I shower today? Or yesterday? And will someone please teach me how to dress cute again? These are the questions I grapple with now.

Here’s the deal, guys: I’m back! Back to share my hard-earned lessons, back to dip my toes in the dating pool, back to tell you all about the lovely and not-so-lovely gentlemen I’m meeting, the mistakes I’m making, and the wisdom I’m gaining as I try to date, and fail, and try again.

But sprinkled throughout my dating stories, I may also lay down a little truth I’ve come to embrace over the past four years of not dating that’s been freeing and fabulous.

Can I lay this one on you right now? If you’re single, and you don’t want to date, THAT’S OKAY. There’s nothing wrong with you, and I know that because I spent many months wrestling with this very issue. I finally came to the conclusion, with the help of some very wise friends and a skilled therapist, that being a middle-aged, unattached, and very single woman without a destination wedding in sight is a pretty bad-ass thing to be. Some of you may be like, “Well, duh, of course it is.” I think I would have said that, too. But the problem was, I’m not sure I really believed it—not for the long-term, anyway. Now, I would say that I have no fears about being alone and give zero fucks about eventually finding love again. If it happens, great! If it doesn’t, my life will rock on, nevertheless.

It took this four-year hiatus from dating for this reality to sink in: I am exuberantly happy with who I am and the life that I live today because I am the one who’s orchestrated it all. I’ve taken myself on adventures, I’ve invested time and money into growing both personally and professionally, I’ve surrounded myself with positive, uplifting, authentic people — and let go of the ones who aren’t. And I have dated myself. Turns out, I may not always be a cheap date, but I sure am a fun one!

I’m going to continue to date myself . . . but I’m also going to be opening up the door to friendships with men again. And I’d love to have you come along with me for the ride. Again. I have a good feeling that the past four years of not-dating have put me in a good position to make some wiser choices for when I AM dating. (And for reference, you can see how bad some of my choices were before my dating hiatus by reading, well . . . most of the entries before this one.)

Let’s go, girls.


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