I’m A Single Mom — & I’m Dating For The First Time Since I Lost My Husband

In 2008, I married the love of my life. In 2019, I downloaded my first dating app.

In the years in between, I built a life with a man who made everything better. We bought a home, we had two children, we cooked and played and traveled together. Then, he was diagnosed with brain cancer — and we lost him.  

Back when we got married, I was sure I’d never date again. But by 2019, while sitting at dinner across from a couple whose effortless banter knew no bounds, I was struck with the realization that forever was a long time to be alone. I didn’t want to spend the rest of my life as a third wheel. So, I figured I might as well learn what all the hype was about when it came to dating apps. 

Let me tell you, it was just as I’d feared: the ghosting, the unsolicited photos, the anxiety that came with opening up to a man who was not my former husband. On the other hand, there were plenty of things I couldn’t predict as well: Namely, that I’d actually meet someone I connected with. 

When I first joined “the apps,” I was merely hoping to chat with another overwhelmed, solo parent. I wanted to dip my toes in before I truly got back out there. But after chatting endlessly online with a kind man named Evan, I determined that meeting in person might be worth a shot. Our first date — in the midst of a pandemic — was a socially distanced walk around the neighbourhood sans recent haircuts or manicures or any of the frills I’ve always associated with first dates. We continued to walk or to sit outside and drink coffee over the course of the next few weeks, and by date five, we were sitting six feet apart in my backyard, talking until nearly sunrise. 

I didn’t rush to tell my children, both of whom are still under 10, that I’d started dating again. I went on most of my first dates with Evan in secret, in the hopes of ensuring he was worth pursuing before I brought my kids into the picture. But finally, after months of avoiding questions about why I was going out dressed “fancy,” it felt only appropriate to clue them in. Solo parenting works best when it’s built on trust, and each half-truth chipped away at that trust. I owed them a proper explanation.

When I finally told them, they were excited. Sure, there was a fair amount of trepidation — rightfully so — but mostly excitement. It’s not that they’d been looking for someone to take their dad’s place — we all know he’s irreplaceable. But that doesn’t mean they’re immune to wanting someone to be present and care for them, or love them, or simply play with them. And while Evan and I weren’t serious enough for proper introductions at the time, I addressed the broader notion of dating with my kids — and I was immediately struck by their enthusiasm. I could tell how high their hopes were soaring — my daughter even described the dress she’d wear to my future wedding. 

Frankly, it gave me pause. The last thing I wanted was to dash those hopes after all that they’d been through. My heart felt hardened to the idea of romance, but theirs were still soft and malleable and vulnerable. From the get-go, I knew I’d have to be more careful with their emotions than I’d need to be with mine. In many ways, dating as a single mom, felt like putting three hearts on the line instead of one. 

With that in mind, I was determined to move slowly. I call Evan my boyfriend now — but we spent six months together before I would let him anywhere near my kids. In those six months, with the pandemic raging outside and date night options thoroughly limited, we built a foundation. Over countless late nights, we dove deep into each other’s value systems, political beliefs, childhoods, and personal traumas. I wanted to know him through and through — and I wanted to be sure he wasn’t going anywhere. 

Ultimately, it was my kids who pushed to meet him. They wanted a face to put to the name they’d already heard stories about, in spite of my reluctance. And while their relationship with Evan has come a long way since their initial meeting, the first time he came over for dinner, things felt tense. My son flossed his teeth with a strand of spaghetti while staring Evan dead in the eyes. Evidently, he was the man of the house — and he wanted Evan to know it. To his credit, Evan barely batted an eye. He was raised by a single mother and a stepfather, and he knew from experience that the only way to gain my son’s trust was to play along.

It worked. More than a year later, we’re in an entirely different place. Both my son and daughter look to Evan with reverence — he’s become a resource to them in ways I can’t be. He’s been teaching them how to play lacrosse, and he has shown them how to use a crab trap (it requires raw chicken and string, in case you were wondering). They joke and make up stories to tell him when he’s on his way over. Sometimes, they even team up with him to tease me. Our loyalties have shifted and broadened. And that’s a beautiful thing. 

Most nights, before I’ve said anything at all, they beg him to sleep over — or they wonder why he’s not joining us on a family trip. When we’re all together, I can see the ways they’re rebuilding their conception of “family unit” around him. They’re finding the glimmers of a happy ending in spite of the tragedy they’ve already endured. Sure, in some ways, their hearts will eternally belong to their dad. Mine, too. But we’re all learning to expand that space to include someone new, together. 

Of course, it’s all easier said than done. No matter how delighted they are, I can’t seem to lean all the way in. Not yet. In truth, it all feels too precarious. Rather than run toward that new version of “family unit” as fast as they seem to be hell-bent on doing, I find myself growing more cautious with each new step. I’m slowing us down to protect them.

On the other hand, I do know that “safe” is a double-edged sword. I’m passing up on occasions, or dates, or modes of intimacy because I’m afraid of loss. I’m holding back. And luckily, for now, Evan is patient. He understands; he doesn’t take my hesitation as rejection. He has his own reasons not to push us toward arbitrary milestones at breakneck speed — and I respect that. But I fear that his patience might one day run out. As it turns out, even safety comes with its own risks. 

The truth of the matter is this: My kids and I are intimately acquainted with loss. We know what it’s like to sit in a hospice room and hope, voraciously, for things to change. Or, at the very least, for the opportunity to say a perfect goodbye. And while I know another loss won’t kill them — or me — I do know that we’re all in a tender state. We’re certainly not prepared to weather more heartbreak. At least, not yet. 

But as much as I’d like to protect my kids from loss eternally, I don’t want them to live a life ruled by fear. And personally, I don’t want to live that way, either. I want my kids to grow up capable of keeping their hearts open to new people, new experiences, new ways of processing the world. I’m inspired by their optimism and their openness. I want them to teach them that, in life and in love, the reward is worth the risk. Sure, that requires a certain fortitude and a willingness to be vulnerable. It requires an understanding that people will come and go for a million different reasons — and that we’ll all continue on nonetheless. But in the end, it’s evidence that loss is a part of life. We have to live, anyway. 

These days, whether or not I feel entirely ready, I’m trying to set an example. It’s my job to teach them what it looks like to love with your whole heart. What it looks like to stare fear in the face and choose hope. So yes, I’m moving slowly on their behalf. But at the same time, I’m learning a version of vulnerability that I could never imagine addressing without their influence. I’m learning to lean in, in spite of my hesitation, simply because it feels like the right thing to do. 

There are no guarantees in this life — even the strongest relationships are subject to dissolution. I can’t unlearn that fact, no matter how hard I try. But I can prove to myself, and to them, that love is worth it, even if it comes with loss in tow. And trying to protect myself, or my children, from loss would be shielding us all from life, too. That was never the plan. Not in 2008, and certainly not now.