Jon Bailey of 2 Dads With Baggage

Episode 65 features Jon Bailey, half of the "2 Dads With Baggage" you may know from Instagram, Twitter or their website.

As is par for the course of the podcast: Jon and I talked about the history of his family for a bit to start. We didn’t dig into these things explicitly, but it was very interesting that he had family members that came to America on the Mayflower in the 1600’s.

Jon talked about the very loving family that he was raised in. It was his big brother and himself, with their Mom and Dad. We breezed through some of his education years, which included both Jon and his brother attending UC Berkeley in Northern California… in very distinct and different eras; Jon’s brother, attending in the ’70s as a "full-on hippie". And, Jon followed suit, but during the ’80s.

Jon took Journalism in college, which led to an eventual internship that, for the best, drove him away from journalism. Jon then went into Public Relations, which stuck for him. An internship in a PR firm evolved into a long-term career for the fresh graduate. A decade or so later, Jon found himself in Marketing, eventually finding a partner and creating his own firm.

Jon loved writing. That was his creative outlet and that was how he found himself creating 2 Dads With Baggage.

In a very tongue-in-cheek kind of way, I really played a lot at not divulging Jon’s husband’s name until the middle of the episode. It is kind of like that cliffhanger on a TV show that people come back the next week for and maybe (if you don’t love his name as much as me, that is) throw their hands toward the television in disgust at the build-up. But, hey… all in good fun, right?

We talked about the vast difference between familial backgrounds Jon and his husband come from. Jon’s parents were happily married throughout their lifetimes. His husband, on the other hand, his parents were married 5 times each. Not to be outdone, his grandmother was actually married 8 times. We agreed that when I go down the road of Grandmothers Unscripted, that would be a great story.

This led into us talking as well about the difference between Jon’s husband’s coming out as gay to his family compared with what ended up being Jon’s experience. One of life’s tragedies: Jon’s Mom’s "hang-up" when she found out he was gay was that she really wanted grandchildren. Very sadly, Jon’s Mother passed away a week before Jon and his husband’s first daughter was born.

The story of how Jon and his husband met and started their relationship is straight out of a movie. It really should be a movie. If their movie was made in the ’90s, I could see someone forcing it to be a straight couple and having Tom Hanks and Meg Ryan star in it. But, let’s do this movie now…it’s 2019! So… you can think about who you would cast in it when you’re listening to this episode. But, tell me that their story and then how their story and lives progress into adopting their daughters go isn’t something you could see yourself watching on the big or small screen.

The stories of the two of them adopting their daughters are each dynamic and unique and incredibly heartwarming. The adoption process has evolved over the years. Having 6 adopted siblings myself, I have heard a lot about it. But, that’s my parents, as standard home providers: a husband and a wife. I am not at all that blind to think it would be the same for two men providing a mother-less home.

Let’s face it: there are definitely things that are more difficult for people in the LGBT community. (I actually looked during this post and realized that this acronym now extends to be LGBTQQIAAP now. Did you know that?!) But, for two Dads to adopt a child, I’m sure there has been quite an evolution over time in that specific process. So, the stories of what they went through to adopt their two daughters are beyond remarkable.

Jon then goes into the inspiring story about how their elder daughter wrote a letter to then President Barack Obama about their unique family dynamic. Jon took a photo of the letter and put it on his social media and it went viral. Quickly. Long story short, soon after they mailed the letter, a personally written letter from President Obama arrived at their home. This, of course, also went viral. This beautiful correspondence between the two just bursts with humanity and graciousness and love that we all need in our lives.

Here is a link to a story on the letters back and forth between Sophia and President Obama:

Jon finished out the episode detailing the creation of 2 Dads With Baggage and what it’s evolved into for them. It’s refreshing in the world of "travel blogging" and all of the myriad of Instagram influencers to see things through the lens of 2 Dads With Baggage. I absolutely encourage you all to check them out and give them a follow. Tell them Daddy Unscripted sent you and… well… I can’t say what will happen. But, Jon and I will both get a hoot out of that for sure!

You can also check out all things 2 Dads With Baggage by simply going to their website at: and just how awesome is their logo? I love it!

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Daddy Unscripted is proud to be a part of the Osiris Podcast Network! You can check out the Osiris Pod website to see what other great podcasts are part of the network by going to

Intro and Outro music proudly provided with a partnership by Umphrey’s McGee.

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