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HBO and The Ringer's Bill Simmons hosts the most downloaded sports podcast of all time, with a rotating crew of celebrities, athletes, and media staples, as well as mainstays like Cousin Sal, Joe House, and a slew of other friends and family members who always happen to be suspiciously available.
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In this special full-circle episode of Dateless in Delray, Susan sits down with Brian Howie—host of The Great Love Debate podcast, owner of PodPopuli, and her very first guest 42 episodes ago. Together, they riff on the realities of modern dating: from the highs and lows of dating apps to the revival of matchmaking, the dream of meeting “organically,” and what the future of love might look like. With his signature candor and sharp insights, Brian unpacks why singles are more connected—and more confused—than ever, while Susan shares how his coaching and support helped her grow as a podcast host. This lively conversation is equal parts funny, frank, and forward-looking, reminding listeners that love is always evolving, and so should we. If you’ve ever wondered whether you should swipe, hire a matchmaker, or just hang out by the avocados at Publix—this episode is for you.
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