In this Dear Guyset episode, I answer the modern dating questions guys are actually dealing with but rarely know how to talk about. What do you do when your friends don't like your girlfriend? Is it possible to go back to being friends after hooking up? Can you date multiple people early on without being a bad guy? And what should you text when she cancels a date?

We talk through real situations around early dating, mixed signals, friendship boundaries, paying on dates, dating apps, and navigating modern dating rules without overthinking every move. This episode is about handling dating with clarity, confidence, and respect for yourself and the people involved.

If you're confused about dating dynamics, struggling to balance friendships and relationships, or wondering what the "right" move is in today's dating culture, this Dear Guyset episode breaks it down in a way that actually makes sense.

This episode is for anyone navigating early dating, blurred friendship lines, or trying to make sense of modern dating expectations.

Timestamps

00:00 Welcome to Dear Guyset
02:30 My friends don't like my girlfriend. What should I do?
10:15 Can you go back to being friends after hooking up?
16:55 Should I accept if she offers to split the bill on a date?
21:20 Is it bad to date multiple people at the same time?
26:10 What should I text when she cancels a date?
30:35 Is it embarrassing to meet someone on a dating app?
35:10 When is it okay to sleep together? (next Dear Guyset question)

Have a question you want answered in the next Dear Guyset? Submit it at guyset.com or DM me @guysetpodcast.

Watch the full episode on YouTube: @guyset

Instagram: @guysetpodcast

Ask Me Anything: https://guyset.com/ask-me-anything

More from Guyset: https://guyset.com/

See you guys next Tuesday!