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 today’s 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!

Episode Timeline
00:00 – Intro: Sydney Matthews joins the show
01:30 – Dating App Burnout & Why Ghosting Happens
04:15 – Sydney’s Thoughts on First Date Nerves
06:40 – The “Show Your Personality Fast” Trap
09:10 – What Makes a Great First Date?
11:30 – Why the 3-Date Rule Actually Works
14:05 – Authenticity vs. Performance on Dates
16:50 – How to Be Intentional Without Being Intense
19:35 – Sydney on Modern Masculinity & Confidence
22:10 – Dating in Your 30s vs. Your 20s
25:00 – When the Spark Isn’t Instant—Should You Still Go?
28:20 – Real Talk: Being Honest About What You Want
31:00 – When “Cool” Becomes Confusing
33:30 – Why We Set Expectations Without Communicating
36:00 – The Little Moments That Create Connection
38:45 – Sydney’s Advice for Overthinkers in Dating
41:30 – Final Reflections: Self-Worth and Standards
44:00 – Outro: What It Means to Date with Purpose

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