Can You Love Someone and Still Cheat? (w/Sydney Matthews)

Welcome back to FROM — a First Round’s On Me podcast production. Today’s guest is one of the internet’s favorite flirts who has the kind of energy you can't scroll past — Sydney Matthews. She’s clever, fiery, and somehow always knows the perfect thing to say — or, the worst thing to admit. In todays episode, we’re diving headfirst into the deep end of dating chaos — from delusional flirting tactics that somehow work, to controversial dating takes, and the beautiful mess that is modern romance. Nothing is off limits, and no red flag is safe. It’s everything you didn’t know you needed. Sydney Matthews, welcome to the show!00:00 – Intro: Sydney Matthews joins the show01:30 – Dating App Burnout & Why Ghosting Happens04:15 – Sydney’s Thoughts on First Date Nerves06:40 – The “Show Your Personality Fast” Trap09:10 – What Makes a Great First Date?11:30 – Why the 3-Date Rule Actually Works14:05 – Authenticity vs. Performance on Dates16:50 – How to Be Intentional Without Being Intense19:35 – Sydney on Modern Masculinity & Confidence22:10 – Dating in Your 30s vs. Your 20s25:00 – When the Spark Isn’t Instant—Should You Still Go?28:20 – Real Talk: Being Honest About What You Want31:00 – When “Cool” Becomes Confusing33:30 – Why We Set Expectations Without Communicating36:00 – The Little Moments That Create Connection38:45 – Sydney’s Advice for Overthinkers in Dating41:30 – Final Reflections: Self-Worth and Standards44:00 – Outro: What It Means to Date with PurposeIf you’re loving the conversation, hit that like button, drop a comment with your thoughts, and hit subscribe for more unfiltered dating talk on First Round’s on Me!Download FROM: https://firstroundsonme.coInstagram: / firstroundsonmeTikTok: / firstroundsonmeappJoe:https://www.instagram.com/firstroundsonjoe/Hannah :https://www.instagram.com/hannah_glasby/Exclusive Offer - Transform Your Dating Life Today!Say goodbye to swiping left and hello to real connections! First Round’s On Me helps you skip the awkward stages and find meaningful matches. Get a FREE month of FROM’s premium subscription—all you have to do is use our code DATING!