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 spent all of my spare time drafting chapters (multiple times) written about my life with my husbands, including his cancer diagnosis, treatment and loss.
What a juxtaposition: meeting not one but two men in that time, who left me wondering what it might be like to know someone intimately again, all while reliving Bren and my love story—and his loss—on repeat. It was quite a head f@ck, to be honest. Welcome to the mind-field, I mean, minefield, of me dating, post-fifty, as a widow. 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, ghosting was just being rude, and people met each other in real life. Like at bookshops (might be handy that I own one of those), bars or through friends, not swipe-fests with names like “Plenty of Fish” (I made that up; I’m not really looking for Jesus and have never been on Tinder. 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 wrinkles and a bit more collagen. Now? Now it just feels weird. But with practice, I’m sure I’ll find my way again, and in the meantime, it’ll be a bit of fun.
Indecision & Self-talk
And so what of the voices in my head? You know the ones saying:
“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?”
“Do I have the energy to jump on another rollercoaster?”
“Am I ready to forgo peace for pleasure, and will I even have to?”
Can I trust what’s real and what’s not? Especially now that nearly everyone uses dating apps, or hook up on socials, which, by their very nature, encourage a level of dishonesty I don’t like. 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.
Some days I feel 100% empowered and ready. Other days, you’re likely to find me on the lounge 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 triggers a wave of guilt that hits me like a brick. 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 complicated? Yes. But aren’t we all? 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 about 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 painstakingly created over the last eight years?
I have had conversations with Tyz and Bades, my sisters, nieces, nephews, and closest friends, about the possibilities ahead. I’d be lying if I said it wasn’t awkward. Seeing me with someone new, even after all these years, will probably still 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 for me at this age and stage? 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. That said, it would be nice to have someone to 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 won’t work. Now that’s going to 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 learned a lot from both, and I have absolutely no regrets about either.
So what did I learn? I’m looking for someone who lifts my energy rather than drains it, respects my past, and brings honesty, fun, laughter, and calm 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 ever, 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 that the whole dating post-fifties adventure (for me anyway) 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 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 free tip: 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! DM me.
Cheers, friends, the world awaits!
Note to the Reader
The 12 posts that follow this one are the drafted chapters I mentioned earlier – they may give a little more context to my dating dilemmas 😊
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