Why I Changed My Mind About Dating Someone With Kids

The ultimate challenge, responsibility, honor, and privilege.

James Michael Sama
8 min readJun 30, 2021


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.



James Michael Sama

I help you evolve into the ultimate version of yourself. Life & Executive Coach. Multi #1 writer. Trusted by: CNN, CNBC, NY Post, CBS, more. Say hi! @JamesMSama