Episode Details
Dating Again
Season 2 Episode 10
Dating Again
Episode Summary
"You’re not only experimenting with dating, you’re experimenting with your new self,” says Ken Brown as he joins The Solo Dad Podcast along with Ben Janoski to discuss what it means to return to the dating world as young widowers with children. Some of what’s discussed, such as ghosting, how soon to meet in person and getting catfished, will be familiar to anyone navigating the contemporary dating world. More unique is what they dub the ‘picture purge,’ which is how to feature mementos of your dead wife in a way that doesn’t erase her from your daily life, while not scaring away your new partner, and allowing you to have control over the space which now belongs to only you.
Ben brings up an excellent point that often the guilt and hesitation you feel, or even the words you put into your deceased loved one’s mouth about dating someone new is really an emotional safety mechanism, because you don’t want to go through the devastation of loving and losing someone again. The only answer is just to get out there and do it, let it be weird and awkward, and see how you feel. Observing how a potential new partner acts around the presence of your loved one’s memory can be a test as to whether they are worth dating.
There is always space for your loved one even as you continue your new life with a new love. Still it’s important to carve out your own space and continue to be happy in the way your loved one would want you to.
In this episode of the Solo Dad Podcast, Matt and Ben dig into the complicated emotional reality of dating after loss—especially the guilt, uncertainty, and fear that can show up the moment you consider moving forward. The conversation isn’t about “tips” for dating apps or trying to rush into a relationship. It’s about readiness, honesty, and learning how to date without abandoning your grief or betraying the person you lost.
Matt and Ben talk candidly about how dating after losing a spouse is fundamentally different from dating after a breakup or divorce. They discuss the internal conflict of wanting companionship while still feeling deeply connected to a late spouse, and how that conflict can create self-sabotage, emotional walls, or unrealistic expectations. The episode explores why widowers often feel like they’re doing something wrong simply by feeling attraction or curiosity again, even when those feelings are normal and human.
A major theme of the episode is timing and emotional readiness. The guys reflect on how loneliness can push people into dating before they’re prepared, and how “being ready” is less about a timeline and more about emotional capacity. They discuss the difference between looking for connection versus looking for someone to rescue you from pain, and why dating can become unhealthy when it’s used to numb grief instead of integrate it.
Parenting also plays a central role in the conversation. Matt and Ben talk about how kids change the stakes of dating, including fears about introducing someone too soon, protecting children from instability, and navigating the reality that you can’t date like you did before. They discuss how transparency, boundaries, and pacing matter more than trying to control every outcome, and why kids often pick up on emotional shifts even when adults think they’re hiding it.
The episode also touches on communication—both with a new partner and with yourself. Matt and Ben reflect on the importance of naming grief, setting expectations early, and choosing someone who can hold space for a late spouse’s ongoing presence. They discuss why the right partner won’t compete with the past, but will still require you to show up in the present with intention, honesty, and emotional responsibility.
This episode isn’t about finding the perfect relationship. It’s about learning how to move forward without shame, recognizing that grief and love can coexist, and giving yourself permission to start again without erasing what came before. If you’re a widower, solo dad, or grieving parent navigating dating, guilt, and emotional readiness after loss, this conversation will feel real, validating, and grounding.
Enjoy Our Podcast?
Consider Making a Donation
We're grateful for your interest in our podcast. If you enjoyed the podcast, please consider making a small donation to support us in continuing to bring you or a loved one engaging content and valuable insights that can assist in the ascension from grief.
