Dating as Papa Jamie in My 30s and 40s:
What I Learned
A Valuable Gift For Our Grandkids
May 5, 2025
When you’re single and dating in your 30s and 40s, people expect certain things. They expect you might have kids. They expect some life experience, maybe even a divorce or two. What they don’t usually expect is grandkids. And that’s where things got interesting for me.
Becoming a grandfather young wasn’t something I planned or even thought about when I imagined my future. But life has a “funny way of writing its own story”. (I use the word FUNNY loosely!) I love my grandkids more than anything, but when it came to dating, it added a layer I hadn’t anticipated. Suddenly, conversations that should have been about favorite foods, travel dreams, or childhood memories turned into me explaining my family tree—and watching the other person try to process it.
Some I dated were incredibly understanding. They thought it was cool that I could be a young, active grandpa. They loved that I could still run around with my grandkids, chase them at the park, and show up with all the energy and heart of a much younger man. They saw it as a positive, something that spoke to the kind of person I was.
More than once, I heard variations of, “I’m just not ready to date someone who’s a grandfather.” It wasn’t personal, at least not exactly. It was about their own expectations for what dating should look like at this stage of life. Some of them were just wrapping their heads around the idea of dating someone with teenage kids, let alone someone with grandkids. For a lot of people, "grandfather" triggers images of retirement parties and long gray beards—not someone who's still out chasing their career dreams, staying active, and living life still full of dreams and aspirations!
I realized it wasn’t something to hide or be ashamed of.
At first, it stung a little. Actually it stung a LOTT! I questioned if I should even bring it up so early when meeting someone new. Maybe I should just wait until the third or fourth date? Maybe soften the news somehow? But after a few awkward experiences and a little soul-searching, I realized it wasn’t something to hide or be ashamed of. It was part of who I was. Anyone who would be a part of my life had to understand that.
Every date, every conversation, every little heartbreak turned into a learning experience. I learned how to be upfront but kind. I learned how to gauge whether someone was ready for the kind of life I lived—or if they were still trying to figure out their own. Most importantly, I learned that I wasn’t looking for someone who could simply “deal with” my reality. I wanted someone who could embrace it and see the beauty in it.
Being a grandfather in my 30s and 40s wasn’t a burden; it was a blessing—and it made dating a lot more real. No games, no pretending. Just life, with all its messy, beautiful layers. And honestly? I wouldn’t have it any other way.
Dr. James Lott, Jr., CTACC, CDC, CNA, CHOC, PMO, OA, DD, Certified Professional Organizer, is the Founder/CEO of The Super Organizer, LLC, and of the Online Network/Entertainment Company JLJ Media. He is a National Speaker/Teacher and Certified Life Coach. He founded and runs the JLJ Media network of over 80 shows (audio and video).
Certified by the Coach Training Alliance, James has been a Certified Life Coach for the past 15 years. He is certified in General Life, Media, Home and Office Organization, and Divorce Coaching. James also holds a Doctorate in Divinity. He also has the weekly Grandparent podcast, Really! I’m a Grandparent and was a Board Chairman of both the SF Church of Compassion and the Harvey Milk Institute.
10 years running, James has one of only several weekly Organizing shows called THE SOS SHOW with James Lott Jr. James is a Number One best-selling Amazon author and has over 60 books. He has several published songs about Organizing. He has been featured in Forbes, Homes & Gardens, Apartment Therapy, and made history on Jimmy Kimmel Live in 2021. James just celebrated 16 years as a Professional Organizer.
James is also a National Keynote Speaker speaking for organizations like: The National Association of Productivity & Organizers, National Association of Perinatal Social Workers, Culver City Garden Club, and Transworld Schools. And has a presentation on UCLA website.
James is a father of two grown daughters and four grandsons and one granddaughter.
