The Dating Game

By Callie

After many years on my own, the idea of dating is back on the table. And the timing couldn’t be stranger. From May through to August, this year, I have drafted a memoir, Love, Unbroken (four times) about my life with my husband, including his cancer diagnosis, treatment and loss.

What a strange juxtaposition it was, meeting two men, both interesting, in that same period of time. I hadn’t looked at another man (well there was that one time a couple of years back, but he’s on the other side of the world) in the eight years since losing my husband. As odd as it felt, those unexpected encounters have made me consider getting to know someone intimately again. I have to say though, getting to know each of them, even just a little (at different times, obviously) while constantly reliving Bren’s and my love story—and his loss—on repeat, was a complete head f@ck. Welcome to the mind-field, I mean minefield of me dating post-fifty, as a widow, in a small town where everyone knows me. Let me be real for a minute, it’s weird.

Starting Over

I was married for a long time, so the last time I dated, we didn’t have smartphones, and ghosting wasn’t a thing (that was just “being rude”). People met each other in real life places, like bookshops (might be handy that I own one of those), bars or through friends at dinner parties, not swipe-fests with names like “Plenty of Fish”. (I made that up, I’m not really looking for Jesus). There will be no swipe fest for me; the thought of swiping left or right on some poor guy, because of how he or I, for that matter, comes across in 2D and a quick bio, for better or worse, gives me the ick. But that’s just me.

I remember flirting, person to person. I think. Vaguely. It used to come naturally, back when I had fewer laugh lines and slightly more collagen. Now? Now it feels foreign. But with practice, I’m sure I’ll find my way again, and in the meantime, have fun practising.

Indecision & Self-talk

Let’s talk about the voice in my head. You know the one:

Am I ready?

My life is great as it is. Why would I change it?

What will people think?

Will I compare him to Bren?

Will I, gasp, have to shave my legs regularly again?

Do I want to break my vow of celibacy? (Come again? I hear you say. Yes, celibacy, it’s a thing, a choice)

Do I have the energy to jump on another rollercoaster?

Can I trust what’s genuine and what’s not? Especially now that nearly everyone uses dating apps, which, by their very nature, encourage a level of dishonesty I am not used to. Or so I’ve heard. Just because someone says they’re nice doesn’t make it true. Or maybe they are. The confusion is real, even in your wiser years. And noise from the outside can be deafening, when you know as many people as me.

Some days I feel 100% empowered and ready. Other days, you’re likely to find me curled up watching The Notebook, judging Ryan Gosling for setting unrealistic expectations and deciding that no man alive could handle the beautifully complicated woman I’ve become. Well, not really, but you get the gist.

The Guilt. The Bloody Guilt.

So here’s the real crux of the matter. Even thinking about dating can create a huge amount of guilt that hits me like a rogue wave mid-ocean. After all, I’ve never stopped loving my husband or feeling like I’m married. I have had the rare privilege of being loved deeply. And I have lost greatly. There’s no guidebook for how long you’re supposed to wait or how much space you’re supposed to leave for the one who’s gone. It’s different for every widow or widower. And I can’t quite believe I’m having this conversation now.

Am I really complicated? Yes. But isn’t everyone? I think so.

What am I looking for? What am I expecting? I’m not sure, but I know what I’m not looking for, and that there’s life to live. There’s laughter, yearning, and curiosity to experience. And, I know that doesn’t erase what I had with Bren. Deep inside, I feel it honours that I survived something I thought was unsurvivable. But I worry how moving forward into a new chapter might affect my kids, our family, and friends if the unthinkable happens and I meet someone new. Like a real contender. How am I going to fit them into a life I already love without upsetting my applecart, you know, the one I have painstakingly built over the last eight years?

I have had conversations with Tyz and Bades, my sisters, nieces, and closest friends, about the possibilities ahead. I’d be lying if I said it wasn’t incredibly awkward. Seeing me with someone new will probably always feel strange for them. But at least we’ve opened the door and had the chat. The one thing I know for sure? My happiness is all they care about.

The Weird of it All

What does dating mean these days? (Thoughts welcome). I know it isn’t about finding someone to complete me; Jerry McGuire and Dorothy Boyd, you have a lot to answer for. Not one of us needs someone to complete us. You are a whole person. Let me repeat that. You are a whole person. That’s one thing I’m very clear on: I am a whole person, I complete me. Having said that, it will be nice to have someone to snuggle with, laugh with, travel with, share with and generally have fun with again. I can see myself with someone new, but I’m a lot, so I’m guessing he’ll have to match my weird, or it’s not going to work. Now that will be interesting.

So what of the two men I met recently? One will always be a friend, I think; the other, I’m not so sure, I’ll keep you posted, maybe! I have already learned a lot from both, and I have absolutely no regrets about either.

So what did I learn? I need someone who lifts my energy rather than drains it, and who respects my past, while bringing honesty, calm, fun, love and laughter, to the time we share. I’m not looking for forever right now; I’m more interested in what’s happening next weekend. I’m also not looking to share my home or theirs anytime soon, or maybe not at all, permanently, but I’m sure sleepovers could be arranged.

So, To Date or Not to Date? I say date—what’s the harm? I’m beginning to understand the whole dating post-fifties adventure is equal parts hilarious, terrifying, unexpectedly healing, and a chance to redefine what connection means. Stepping into a new chapter, not because I’m replacing Bren, but because I’m still growing, still curious, and still me, is possibly worth the time invested.

So, if you’re also out there wondering whether to date, remember: it’s your timeline. Your rules. And your dating story to tell, preferably with a killer outfit and a backup plan to escape if he (or she) turns out to be a flat-earther. Oh, and a tip for free: it can be a good idea to step outside your hometown. You don’t want to run into the flat-earther every time you’re at your favourite coffee shop or hanging out at your local beach.

Caveat: I have not met a flat-earther, but can only imagine how fun arguing the ridiculousness of that idea would be.

So to finish, here is what my gorgeous friend said to me recently when we were discussing whether or not it was time for me to jump back into the world of dating: “Cal, whatever you choose, own it. You’re not the same woman you were in your twenties, thirties or forties. You’re braver, wiser, funnier, and have way better taste in wine (my taste in wine is debatable). And if nothing else, at least bad dates will make for great stories.”

That, my friends, is true for all of us. Maybe I’ll soldier on! Or, at the very least, live vicariously through you when you do. 🤣 Don’t forget, I want to hear your stories too!

Cheers, friends, the world awaits!

📖 You can find Love, Unbroken here on calliemm by searching “Love, Unbroken.” The 4th draft of all twelve chapters, along with the Introduction, Prologue, Epilogue, and Love, Unbroken: Whispers—are available as individual posts.

2 responses to “The Dating Game”

  1. Nish Avatar
    1. calliemm Avatar

      Thank you 😊

      Like

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I’m Callie

A storyteller, widow, mother, and founder of Kalico. I share stories about life, love, loss, travel and starting over.