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Dating After Divorce, Open Relationships & Finding Love in Montclair

Michael Schreiber October 23, 2025
(Updated: October 24, 2025)

Montclair is nothing if not opinionated about schools, taxes, pizza, and, as we learned on this week’s episode of The Montclair Pod, dating. We invited relationship expert (and proud local) Junie Moon to help map how mid-life love actually works here: online and off, traditional and not, public and very, very private. What emerged was a grounded, hopeful field guide tailor-made for our town.

Moon didn’t come to this work as an armchair theorist. She’s built her practice around people beginning again in the thick of life, and she’s transparent about why.

“100% because I lived it,” she told us. “I lived the divorce, I lived the starting over… carrying a bag of my past along with me on those dates. And I realized that it can be different.” That word—different—is core to her approach. You aren’t recreating your 20s; you’re building something that fits your actual life now. In Moon’s lexicon, that’s a conscious partnership: intentional, value-aligned, and right-sized to the second half of life. As she put it, “People are really hungry for love… they’re really wanting partnership.”

If you’ve sworn off apps, Moon wants you to reconsider—but not in isolation. She’s the first to say the sweet spot in Montclair is both/and.

Swipe right vs Real Life

On her own experience: “One swipe, baby, one swipe,” she laughed, then stressed that results like that aren’t magic; they’re process. “Online dating works, and most people don’t know how to do it right. There are strategies… ways to streamline it so it doesn’t feel exhausting or a full-time job.” The counterweight to screen time? Showing up where Montclair shines. “Take advantage of the Montclair Film Festival or… the museum. There’s so many wonderful things,” she said, arguing for a hybrid plan. “Put the two together, you’ve got great potential.”

That “show up” ethic is also built into Moon’s newest project, a talk-show pilot filmed here at home. “It’s called Your Best Life with Junie Moon… and we had a segment called The Ultimate Match,” she explained. The casting skewed to her clientele—“mostly in their 50s and 60s”—and the format kept things honest. “They didn’t know what questions were coming… There was that blind aspect.” The dates themselves doubled down on local love: “The dates are in Montclair… at Faubourg and Thought in Motion cafe. We really wanted to support local businesses.”

As for outcomes, they mirrored real life: some sparks, some misses, some surprises. “Of the three matched, one found that it wasn’t necessarily a match… [but] one of them went on to connect with one of the other people… and one is figuring out when they’re going to meet.” Translation: hope is alive, even if the path is a little squiggly.

Love, Remixed

We also asked about the non-traditional patterns people whisper about at backyard gatherings and on Secret Montclair threads. Are open relationships and living-apart-together really a thing here? Moon answered with candor and caution born of experience.

“When I was married 20 years ago, we opened up our marriage… I experienced that. That’s not my choice… anymore.” She wasn’t moralizing; she was spotlighting the work beneath any arrangement. “I call this… strategic vulnerability. You need to be strategic around how open you are and who you share your truth with… It’s having healthy boundaries… and making sure that you’re really taking care of the other person.” In a town that can feel like a village, discretion isn’t coyness; it’s care—for your kids, your co-parent, and your community. Her warning label was plain: “Most people don’t have the communication skills and the solid relationship dynamics in check before they go there.”

Matchmaker, Matchmaker

On the lighter side: Montclair loves to play matchmaker. (Confession: My wife Vanessa and I introduced a couple that’s getting married next month. Yes, I’m practicing “Matchmaker, Matchmaker.”) But if you want friends to help, don’t be vague.

“‘I’m single, do you know anybody?’… That’s not clear enough,” Moon said. Helpful looks like this: be specific about rhythms and values, not just stats. “Say, I’m looking for someone who loves to be adventurous… maybe has kids the same age. Then people start to go, I know somebody.” It’s simple math: the clearer your signal, the better the match.

Love & Money & Politics…

Because it’s Montclair, touchy subject – especially politics – inevitably surfaced—specifically, how couples are talking about the December 9 school referendum and whether national headwinds are blowing into their living rooms. Moon’s answer was a masterclass in staying connected when you disagree.

“My partner and I… voted differently [for president]… but ultimately we are on the same page when it comes to our values… We love each other, even if we see a little differently.” The point isn’t to mute convictions; it’s to remember the person holding the opposing view matters to you. In a season when everyone’s amped, as Moon said, “Things are intense right now,” respect travels farther than a perfect clapback.

Zoom back, and a Montclair-specific picture of mid-life dating comes into focus. We are a town rich in cultural events and third spaces; we’re also a town where news travels fast. Moon’s framework meets both realities. Show up as who you are now. Use the tools well. Set boundaries that protect what—and who—you love. And if you’re experimenting, do it with eyes open and communication on overdrive.

Learn more about Junie Moon at https://midlifeloveoutloud.com/


Quick hits: MOON’S Montclair-centric dating playbook

  • Own your story. Mid-life dating works when you show up as who you are now.
  • Blend your channels. MFF screenings, museum nights, neighborhood cafés + a streamlined app strategy.
  • Be precise, not broad. When asking friends to set you up, describe values, lifestyle, and rhythms—not just “single.”
  • Practice strategic vulnerability. Share selectively; protect your kids, partner, and community ties.
  • Pick the relationship model that fits your season. Monogamy, living-apart-together, or something else—choose consciously, communicate relentlessly.
  • Lead with respect when you disagree. Values can align even when votes don’t.

Michael is the President and Co-founder of MediaFeed, and an Emmy and duPont-winning journalist and media executive. He's worked with the New York Times, Frontline, HBO, ABC News and NBC News. Mike attended Columbia’s Graduate School of Journalism. He plays keys in Bard and he and his family have called Montclair home for 15 years.

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