EP 48: Great at Dating, Terrible at Relationships: A Celebrity Matchmaker's Unfiltered Truth ft. Alessandra Conti

You've been on the dates. You've felt the spark — or you haven't. You've told yourself you have a "type." You've stayed friendly with your ex "just because." And you've done all of it while genuinely believing you're ready for a relationship.But what if most of what you've been taught about dating is quietly working against you?This week, Madden sat down with Alessandra Conti — Celebrity Matchmaker and co-founder of Matchmakers In The City in Beverly Hills to talk about the single biggest mistake daters make (going for chemistry instead of character), what a man's Instagram following actually tells you, and the real reason why men who are great at dating are usually terrible in relationships. Then we go fully off-script — into whether men and women can actually just be friends, and why staying in contact with your ex isn't harmless, it's self-sabotage.This one is going to make you want to text your group chat immediately.WHAT YOU'LL LEARN:Why chemistry-chasing is keeping you in the same loop — and the question Alessandra says to ask insteadThe one Instagram red flag that tells you a man isn't ready for a relationshipCan men and women actually be just friends? (We have opinions.)Why staying friends with your ex is an avoidant attachment pattern — not just a personality traitHyperindependence as a trauma response and how to start letting people in"People are going for chemistry and not going for character. And this is where we are — welcome to 2026 and the wild, wild west of dating. It's not that chemistry doesn't matter. It's that character is the thing that sustains a relationship once the butterflies quiet down. And most people aren't vetting for character at all."- Alessandra ContiCONNECT WITH ALESSANDRA CONTI:Alessandra Conti is a Celebrity Matchmaker and co-founder of Matchmakers In The City, a personal matchmaking firm based in Beverly Hills. She has served as the matchmaker for Real Housewives of Beverly Hills, NBC's Access Hollywood, TLC's My Big Fat Fabulous Life, and two seasons of MTV's Are You The One. Her advice has been featured in Forbes, The New York Times, The LA Times, and Fox News. Over nearly 14 years, Alessandra has worked with clients ranging from royalty to young professionals, leading a team of six matchmakers responsible for hundreds of marriages.Alessandra's Instagram: @matchmakeralessandracontiMatchmakers In The City: @matchmakersinthecityMatchmakers In The City WebsiteLOVE LAB & MORE🎟️ Love Lab Live Dating Event – Minneapolis, May 4th 📥 Free PDF Guide: The 9 Dating Personalities (deeper breakdown of every pattern) CONNECT WITH YOUR HOST MADDEN ZAPPA:Madden Zappa is a dating and relationship coach who helps people recognize and break the patterns that keep them dating the same person over and over again. Through her podcast "We're Dating the Same Guy," Madden combines vulnerable personal stories with practical frameworks to help listeners date smarter, healthier, and more intentionally. Her approach is refreshingly honest—she's willing to share her own uncomfortable truths and dating mistakes to help others avoid the same cycles. With expertise in attachment styles, dating psychology, and relationship patterns, Madden creates content that speaks to the late-night Google searches we're all too afraid to admit we're making.Madden's Instagram: ⁠@maddenzappa⁠STAY UP TO DATE WITH WE'RE DATING THE SAME GUY:We NOW have an Instagram. Follow us over at ⁠@datedifferentlyco⁠Submit YOUR dating stories and questions: ⁠Date Differently Diaries (completely anonymous)⁠✨As always, we do not gatekeep how to date smarter. If this episode moved you or taught you something new, think it would be beneficial for others to hear, please take a moment to follow, leave a review, and SHARE! Pass this episode along to someone who would love it too or head on over Instagram to share the most recent episode.