Are You Wearing Red Tonight?

In this episode, I’m talking through my day and getting honest about some red flags I’m noticing with a guy I’ve been spending time with. I’m not sure he’s my person, and instead of forcing it, I sit with that feeling and unpack what I actually want. I talk about the kind of man I’m drawn to, why dating older men feels attractive to me, and how clarity starts showing up when you’re finally listening to yourself. In the middle of it all, my best friend calls me out of the blue — and I record the conversation. It’s spontaneous, funny, and exactly what I needed in that moment. A reflective, end-of-year episode about intuition, standards, friendship, and trusting yourself as you head into something new. — Don’t forget to

You can listen to Are You Wearing Red Tonight? online on Radio and Podcast. Open the player on this page to stream the available audio.

Are You Wearing Red Tonight? is an episode from Late Night with Sylvester by Sylvester.

This episode is 27:29 long.

This episode was published on Jan 11, 2026.

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