Rolling into the Labor Day weekend, Donald Trump was able to relax a little on Friday night with a ballroom of smitten women in downtown Washington.

He began the week with a controversy over Arlington National Cemetery and ended the week with what smelled like flip-flop on Florida’s abortion referendum. Mr. Trump needs votes from women, and the Arlington and abortion story lines aren’t exactly winners in that regard. So it was interesting to watch him working to firm up a part of his base, at the third annual convention of Moms for Liberty, a conservative group devoted to “parental rights.” He took a stab at addressing the Arlington mess, telling his cleaned-up version of events and whining about how persecuted he is. But mostly, he tried to offer what he thinks women want — Trump unfiltered. Which is, in his head, the ultimate winning strategy.

No doubt, everyone was in a partying mood. Everywhere you looked, there were women rocking Trump T-shirts and cocktail dresses, cowboy boots and stilettos, ponytails and MAGA hats. But Mr. Trump’s appearance raised the same question as his recent string of North Carolina rallies: If he’s spending time in safe spaces and once-safe states, when will he start trying to win over on-the-fence women and others who may decide the election?

Forgoing his usual rallies, the former president had agreed to a special “fireside chat” with Moms for Liberty. To signal how cozy and Oprah-esque this was going to be, a vase of red roses sat on a small table beside his large white armchair and the one occupied by Tiffany Justice, a co-founder of the group.

Before the event, Ms. Justice shared with me her hopes for the encounter. She wanted Mr. Trump to talk parental rights, of course, but she also wanted folks to see a softer side of him: “He’s a dad. He’s a grandfather. He loves his family. We’ve seen him working with his family in politics and business, right? I hope the American people get to know Donald Trump in a little bit of a different way. He’ll get to express his love for his family. I think that’s going to resonate with American voters.”

In theory, this was a brilliant opportunity for Team Trump, which is desperate to humanize the candidate and get him to talk policy rather than simply slag his political enemies.