On this episode of The Back 9, Dennis and Josh sail back into the world of modern romance with professional matchmaker Shira Weitz for a deep dive on how dating has evolved—especially for those re-entering the scene in middle age after divorce. Shira walks us through the entire process of the when and why one should consider a matchmaker, as well as eye-opening advice — and several funny stories — about profile photo errors, style mistakes and first date blunders.

So whether you're navigating single life post-40 or just curious why your dating apps aren't working, this episode dishes out real strategies to level up your love life. It turns out that matchmaking isn’t old-school—it’s a smarter, curated approach for people who know what they want, but don’t want to waste time finding it. So make a date for this episode of the Back 9.

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