The Best Life Podcast · Danny-J Johnson & Jill Coleman

Ep. 618: Dating Someone With Children

March 18, 2026·25 min·2 clips

Dani reveals how a breakup with a man 20 years older left his daughter heartbroken years later.

The question lands close to home. After a catch-up about Brandon winning Arizona Alumni of the Year for U of A, Jill ties the topic to his friend dating an older man with children. They do not treat it as an automatic no. The take is more grown-up than that: people can choose their own limits, but dating a parent brings in more than the couple. The ex matters right away. If the man is still constantly talking badly about his ex-wife, Dani J. and Jill treat that as a serious warning sign about maturity and unfinished conflict. Being on bad terms is one thing. Staying stuck in contempt and blame is another. The mother matters too, because anyone dating the parent may eventually be around the child. Her comfort is not some annoying side issue. That is where the whole thing gets complicated. They keep coming back to how many relationships are involved, not just the romantic one. Older kids feel easier to imagine. One host says she would only consider dating someone with children if the kids were in high school or nearly done. Attachment is the part that really stings. They mention friends who found that leaving the kids hurt more than leaving the partner after a breakup. That changes the whole calculation. Staying loosely involved afterward might feel kind, but they argue it can be unfair to the child. Distance adds another limit. One host remembers dating someone in another state with one high-school-aged child and knowing she would not move there. After the relationship talk, they close by asking listeners to follow the show, leave five stars, and paste supportive DMs into Apple Podcasts.

As heard by us

Dating a parent brings timing, exes, and the kids into sharp focus.

Dating someone with children is treated as a practical matter, with timing, exes, and the extra care kids require all kept in view. The conversation keeps circling back to whether a parent has a workable relationship with an ex-wife, whether everyone can stay on decent terms,…

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Why you'd press play

If youre eyeing someone older who already has kids, this gives you the family-side reality before you jump in.

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