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Why I Changed My Mind About Dating Someone With Kids

Why I Changed My Mind About Dating Someone With Kids.



James Michael Sama is an internationally recognized speaker, author, and personal development coach.


Here he writes about dating someone with kids


I grew up in a very traditional Italian household. My parents have been happily together for over 40 years. My grandparents were married for over 60. My mom stayed at home with us — though she also runs her own business from there.


The point is, I always saw my future playing out in a very “traditional” way, despite not at all being a traditional type of person.


As I got older, I began traveling and exploring both myself and the places around me. I moved to Los Angeles, spent a month in New York, traveled to different cities for dinner when the invitation arose.


I started to question whether or not I wanted to “settle down” at all, let alone get married, let alone have children…

Let alone…help to raise children who weren’t mine biologically.


Why would I? Life was great. I had the freedom to go where I wanted, when I wanted, with whoever I wanted — and I took full advantage of it.


When the pandemic lockdowns began in March of 2020, Rachel and I casually started chatting online. We’d been Facebook friends for over 10 years so I knew she was previously married and had two children.


But, our conversations were casual and mostly focused around how each of our businesses had been affected by the pandemic.


She owned a 14,000 square foot indoor playground, and I was traveling frequently for speaking engagements. Both, industries that were suddenly halted.


Our conversations evolved and we started having “virtual drinks” over video chat. Then, we’d text each other the next morning — all day, and virtual drinks again.

I knew there was clearly mutual interest and I was learning all about her as a person. Her strength, resilience, ambition, drive, humor…


She’d left an abusive relationship to raise her two children on her own and start up her then-thriving business. We spent hours on video chat (over 20 hours before we actually met in person), and it never got old. We laughed until we cried and talked about everything under the sun.


There were no secrets by the time we met.





This was a level of communication and connection that I’d not experienced with other women I had dated. I knew she was a mother, but my focus was on her as a woman, and eventually, a potential partner.


Independent of her past, is this a person I could see myself growing with?

When we finally met in person, I knew the answer was yes.

A couple of months later, I met the children.

Liliana was too small to hold her own bottle up at the time. I was one of the only men she’d ever spent time around. Rosabella was 4.


As we began sharing more experiences together, a clearer vision of the future began to crystallize in my mind.


The truth was, I wasn’t really sure what my future would look like when I was single.

Many times, I considered being an eternal bachelor, floating around, driving a two-seater car, living in a busy city somewhere, and going out to events and dinner every night.


Spending time around Rachel and the girls as a family, coupled with the pandemic and being separated from my own family, really began to change my views on the next steps I wanted my life to take.




As I started out saying, I was fortunate to have an amazing upbringing and childhood, and have spectacular parents that I continue learning from every day.


I found myself implementing deeper knowledge and lessons around the kids than I even realized that I had. The baby was warming up to me. I was playing with dolls and princesses with Rosabella all the time (and she was starting to get into dinosaurs which I loved).

Things began to flow, and the stigmas I’d once carried about raising “someone else’s” kids seemed to fade away.

You are being gifted a huge responsibility.

Why is raising someone else’s kids a “gift”? I’ll tell you why.

The existing parent has one main priority in their life: Keep their kid(s) safe.

This means that one of the most important decisions they’ll ever make is who they choose for a partner to help raise those kids, if they choose anyone at all.


When you’re two single people dating and building a relationship together, it’s much more casual and carefree. I’d been down that road countless times. It could be fun, but also often empty and void of meaning.


Dating someone with children is much more intentional. They aren’t just determining if you’re a good fit for them, but a good fit to be a father (or mother) figure to the most important people in their lives.



In other words, there’s no bullshit. You’re either in, or you’re out.

You’re also being gifted a huge opportunity.

I know that my brother and I are the way that we are because of our parents. I see it every day in the decisions we make, the way we interact with people, and the way we choose to live our lives. It is obviously and directly influenced by the values our parents instilled in us.

I also recognize that not everyone has the random stroke of luck that we did being born into the family we were.


We can’t control where we are born or what we are taught.


Dating someone with children gives you an opportunity to become a positive role model that will be one of the primary influences in the formative years of someone’s life.

In my case: Two lives.


I’ve spent the better half of the past decade helping women recognize their own self-worth, step away from abusive relationships, and build a deeper sense of confidence in themselves.

Suddenly I was given the opportunity to positively influence the lives of two girls who were already on a path to become powerful and determined women, just like their mother.


Not only that — I was given the opportunity to model what healthy love looks like. Every morning when I kiss Rachel, or tell her she looks beautiful, or offer to help carry things downstairs, I know I am setting an example that is being silently observed.

This is how we create a better future — by showing future generations early in life how to be kind, caring, loving, and compassionate.




This is also how we create a better future for ourselves and our partners — by stepping up and properly loving them in a way that makes them feel fully accepted, free, and whole.

It gives me a deeper sense of drive and direction.

I’ve long had visions of the type of life I wanted to live even if I wasn’t sure where it was going to lead — but I was only responsible for creating it for myself.


Now, others are counting on me to step up to the plate as a teammate and as a winner.

Rachel doesn’t need me to “provide” or “protect,” but you bet your ass that I am driven to do as much of both as I can for her and the girls because that’s what I was raised to believe is part of having a family. You do everything you can to make their lives better and happier.

That is a layer of depth that never existed when I was floating around making short-term decisions.


The gravity and consideration of each choice made has since tripled (literally), which serves as an opportunity for my own personal growth.

“How will this affect the family?” rather than just “Do I want to do this or not?”

It is a challenge, of course, every single day.


As I sit here writing this article there is silence. A silence that I was used to all day, every day, living alone. Now, this silence is a novelty. The few hours in between while the girls are out doing their activities and Rachel is working provide me with small windows where I can write or do coaching calls outside of the office.





The little one is a human alarm clock every morning.

During the short time we allow the TV to be on, it’s musical nursery rhymes instead of James Bond, or Jurassic Park, or car reviews on YouTube.

But, without challenges, there are no rewards.

For the first time, I really feel like I (we) are building towards something. There is a fresh vision of the future that is multi-dimensional. There is teamwork, mutual support, self-improvement, and inspiration.



This isn’t for everyone. For most of my life, I didn’t think it was for me, either. It requires you to be ready for it with no exceptions. There is no practice round, trial run, or mulligan.


If you are going to consider dating someone with children, you damn sure better be up to the task.


This is an infinite journey of learning as we all try to figure things out as we go. We stumble, mess up, apologize, and do better next time. It’s the way of the world and the path to a better life.


If you can find a partner who is willing to hold your hand along the journey of development and discovery, that is where the magic is. Those are the things we need to value in each other.

The ability to laugh together, cry together, adventure together, or simply just sit and exist together.

We never know where someone with these qualities is going to come from, or what they’re going to be bringing with them when they arrive.

Maybe they have kids, maybe they don’t. Maybe they’ve been married before, maybe they’ve not. Maybe they come from the same type of background as you, maybe they don’t.

The truth about love is that it’s not simply something you fall into or stumble upon. It’s something that you consciously choose to build alongside someone every single day and night.


Real commitment is about making the decision to navigate the roads of life alongside someone that you trust and respect as your teammate on the journey.

When you have that, you’ll be able to figure the rest of it out, because you’re doing it together.


James Michael Sama is an internationally recognized speaker, author, and personal development coach.

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