After the incredible response to the first Dad Boss episode, Jason Wright and Abby Neilson are back — this time answering questions submitted by listeners.

And nothing is off limits.

From dating in the age of social media to marriage, singleness, faith, relationships, communication, and figuring out what actually matters in a partner, Jason and Abby bring two very different generational perspectives to the conversation.

Jason shares lessons from marriage and raising daughters, including why small rituals can become some of the most meaningful parts of a relationship. Abby offers the perspective of a young single woman navigating modern dating, friendships, weddings, faith, career, and the pressure to have life figured out.

In This Episode

Jason and Abby talk about:

• Jason's non-negotiables in marriage — including goodnight kisses, resolving conflict, and the surprisingly important tradition of the Sunday morning coffee mugs.
• Why Abby has changed her mind about the idea of "as he should" in dating.
• Whether men should still make the first move — and why women can make it easier for good men to approach them.
• Why asking for someone's Snapchat may officially be a dating red flag.
• The case for putting down the phone, stopping the endless texting, and actually calling someone.
• Why chivalry, kindness, mutual respect, and giving someone the benefit of the doubt never go out of style.
• The difference between accepting someone's flaws and trying to change them.
• Why the right relationship should challenge both people to become better versions of themselves.
• Building a life you genuinely love before asking someone else to become part of it.
• Why hard work, ambition, emotional availability, and effort matter more than someone's current bank account.
• The danger of dating someone's "potential" instead of paying attention to who they actually are today.
• Why assertiveness may be considered a dating red flag by some of Gen Z — when it can actually be a major green flag.
• How social media algorithms can distort our expectations of men, women, dating, and relationships.
• Abby's perspective on navigating post-grad life and wedding season while single — and learning to celebrate someone else's season without questioning your own.
• Faith, patience, and trusting that your timeline doesn't have to look like everyone else's.
• Why preparation, intentionality, and clear communication matter in dating just as much as they do in business and life.

At the heart of the conversation is a simple idea: don't settle — but don't spend your life demanding from someone else what you aren't willing to bring to the relationship yourself.

As Jason puts it, if you want a princess, you'd better be a prince. And if you want a prince, you'd better be the princess.

Relationships aren't simply about finding someone who checks every box. They're about becoming the kind of person capable of building something meaningful with another human being.

And sometimes that means putting down the phone, ignoring what the algorithm tells you relationships are supposed to look like, and learning how to actually talk to each other.

Dad Boss Is Becoming Its Own Show

Thanks to the overwhelming response to the first episode, Dad Boss is officially becoming its own podcast with Jason Wright and Abby Neilson.

Future episodes will include more listener questions, conversations about dating, relationships, career, faith and life, along with both virtual and in-person guests.

Have a question for Jason and Abby or want to join them for an episode?

Email producer@texttitans.com or reach out to Abby on social media.

And if you enjoyed the episode, subscribe, share it with someone who needs to hear it, and leave a five-star rating.

Dad Boss — two generations, two perspectives, and honest conversations about figuring out life.