After 20 Years, My Childfree Dam is Starting to Crack
Because single moms’ kids usually become relatable young adults

Since meeting (online) a single mother of two high school-aged kids, I’ve asked myself this question for a few months. Turns out we had no chemistry when we met in person.
Yet the question stuck in my mind like a corn kernel between two molars. Irritating!
For years I’ve told myself I don’t want to raise kids, including someone else’s. Is my childfree mindset fortress starting to crack? Am I getting soft in my middle age? And the clincher: are older kids really all that bad?
Every situation’s different. Results depend on the kid’s maturity level, personality, and where they are in life. It also depends on the mother’s parenting expectations in a potential romantic relationship.
When is a kid no longer a kid?
Oversimplified answer: it comes down to age. Once the kid is old enough to live independently, they’re a young adult.
I know — I can hear some of you parents thinking, but they’ll always be my baby!
No worries. Ideally, you decided to have a mini-me and devote at least 18 years of your life to molding them into a productive member of society. Kudos.
But think about your progeny’s milestones for a sec: birthdays, best friends, skills, academic achievements, relationships, driving, prom, college, moving. These special moments are great, but they’re also reminders. One day you’ll need to stop thinking of little Tommy or Sally as a child and let them “adult” on their own.
We all know one kid leaving the nest is different than the next. But for purposes of this article, let’s say college graduation is when the young’uns move out and start taking care of themselves.
Time to visit a new nest?
Back to the single mom.
I had asked some single childfree friends if they’d consider dating empty-nesters. A couple said they would, so after some thinking, I decided to go ahead and widen my dating pool.
I won’t deny it’s been easier to get dates. And I’m thankful. But I’m also not a serial dater. Dating is fun for some and a hassle for others, but it’s only a stepping stone. My final goal: find someone compatible to share life’s roller coaster, and spend the rest of my life with.
So, I — and approximately 49 million of my closest single friends — jump through online dating hoops like circus lions. We try to avoid getting roasted by the burning rings of bad relationship juju. And the more we learn, the better our success rate. At least that’s how it’s been for me.
Case in point: The more I spoke with mothers I’ve met, the more I found myself not minding meeting their children. It was a little surprising. Time helps you digest a foreign concept, and over these past two months, I’ve realized a couple things.
If the “child”:
- Is in college or graduated and living on their own…
- Has stepped off the angsty “Mom’s Embarrassing” train…
…then I’m okay with it.
Still, after almost 20 years of calling myself “childfree,” this is new territory. If you’re in the same boat, don’t expect swift answers to all your questions.
If I leave “childfree” behind, what can I expect?
The woman I’m seeing now, a single mother of an early-20s child, is a widow. She’s proud of the woman her daughter is becoming. Life is good.
Enter, Childfree Guy. If the relationship blossoms and we prepare for the long-term, I’ll meet her offspring.
Would Mom expect:
- Me to help if the daughter wants advice?
- Me to bond with her daughter?
- Her daughter to accept me unconditionally?
We’re both excellent communicators. And it’s easier for many folks to talk to a twenty-something than a young child. I’m sure the mother would guide us through this “work in progress” to a place of emotional comfort.
Takeaways
Find your definition of “young adult.” It might help you kick off a potential relationship with a single parent. I first considered the single-parent dating question in February. It’s now April. I’m not 100%, but I’m much more open to the idea. Time breeds familiarity if you let it.
Different family dynamics and personalities play a role, sure. But sons and daughters in their early-20s are much more relatable than pre-teens. That’s my experience. Your results may vary.
No doubt other folks — parents or non-parents — have considered these questions as carefully as I have. I’d love to hear some of your stories!
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