Ask a Widow: Dating is Hard When You Try to Predict the Future

I’ve said it before, but I’ll repeat it again: people write to me all the time about dating.

Usually, I get private messages on my blog or my social media pages. The questions range from the existential (“does it mean I don’t still love my late husband if I want to date?”) to the mundane (“what’s the best dating website for widows?”) I try and answer the questions as best I can, but I’m no expert. I’m merely someone who has written openly about my own experience.

Often, readers give me their backstory before asking me about dating. It might go something like this:

My husband and I were married for 15 years. We met in college, and he was the only person I have ever loved. We have two kids who are 8 and 10 and for the first year, I spent all my time making sure their needs were met. But after a while, I wanted to have something for me, so I started online dating a little bit. I’ve actually been talking to someone lately who seems promising and we’ve shared more and more with each other. But here’s my question: what if we become a couple? What if he turns out to be the second love of my life? If that happens, how will I navigate his relationship with my children?

Usually, when I get questions like these, I try and answer without too many specifics. I have no idea what someone else’s life is like, so I don’t want to presume I have all the answers.

And yet. There’s something about questions like these that make me pause.

“Hold on!” I want to say, “you’re getting way ahead of yourself.”

Listen, I get it. I remember meeting a man about two years ago, the first man I was attracted to after Shawn’s death, and laying in my bed at night thinking, “does he seem like the fatherly type? Could he really handle kids?”

I had known him for a total of two days at that point.

He didn’t become the second father to my children or the next love of my life. He was merely my first fling, and a pretty tame one at that.

But it wasn’t the first time that I projected into the future during the early days of dating. In fact, it was much more common that I’d be on a first or second date and wonder, “if we got serious, would he move into my house or would I move into his?”

It’s kinda embarrassing to write that, actually. I’m a grown-up with three kids and I shouldn’t be acting as though I’d make rash decisions like moving in with a stranger.

But dating as a widow made me want love again right away. I’d had it before, so I knew what it felt like and I desperately wanted it again. In fact, I didn’t just want love, I wanted long-term commitment and a father for my children.

That’s a lot of pressure for a first date.

I didn’t tell the people I was dating that I was thinking these thoughts. I’m not that stupid. But it was still a lot of pressure that I put on myself. And it made dating really hard in the beginning. As time went on, I realized I would have to actively push these thoughts to the back of my mind, at least for the first few dates. I needed to get to know my dates as human beings first.

I think a lot of widows who are dating want to know the future. We have to protect our hearts and our children and our lives and we know that if we fall for someone who is wrong for us, it could be super damaging. We want to safeguard against other bad things happening to us.

But here’s the deal – dating is terrible if you constantly are thinking about the long-term future. Or at least it was for me.

I’m not saying you won’t ever think about the future. If you’re dating at 40, you know yourself and you know what you like. It’s easier to weed through potential suitors because you aren’t necessarily interested in everyone, or at least not in the same way you once were at 22. And yes, we all need parameters around dating, so if I saw someone who wrote on his profile, “doesn’t want kids” I avoided that person.

But I found that putting aside the questions about whether a first date was a potential good father for my children or acceptable life partner for me made those first dates just a little bit easier. It meant I could get to know my date first, and maybe meet someone who wasn’t a carbon copy of Shawn.

I didn’t always do a good job of this. But when I did, it made the process of dating much easier.

And sometimes, it was even fun.