Guyset podcast

Asking Out, Moving On, and Starting New, Dear Guyset

10/27/2026
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Welcome back to another episode of Dear Guyset, where I answer the real questions guys are asking about dating, relationships, career, confidence, and figuring out life in your 20s.

This week, I'm answering seven questions about situations we've all probably found ourselves in at some point. How long should you talk to a girl on a dating app before asking her out? What do you do when you've been on a few dates with someone who's great, but something feels like it's missing? And how do you know if you're doing a good job when you've just started your first real job and feel like you're already supposed to know everything?

I'm also talking about when to introduce someone you're dating to your friends, whether you should tell your girlfriend when something small bothers you, how to become more present in your everyday life, and some last-minute Halloween costume ideas.

I'm not an expert. I'm just another 26-year-old guy figuring these things out alongside you. My goal with Dear Guyset is to share honest, practical advice that helps you feel a little less alone in whatever you're going through.

TIMESTAMPS:

02:29: What should I be for Halloween?

04:00: How long should I talk to a girl on a dating app before asking her out?

10:30: I've been on a few dates with a girl, but something feels missing. Should I keep seeing her?

17:00: How do I get better at being where I am right now?

20:20: When should I introduce the girl I'm seeing to my friends?

23:35: Should I tell my girlfriend when something small bothers me?

27:15: I just started my first real job. How do I know if I'm doing a good job?

33:25: How to submit your own Dear Guyset question

ASK ME ANYTHING:

Have a question about dating, relationships, confidence, career, or life in your 20s? Submit it anonymously at https://guyset.com/ask-me-anything for a chance to have it answered in a future Dear Guyset episode.

MORE FROM GUYSET:

Website: https://www.guyset.com

Instagram: https://www.instagram.com/guysetpodcast

Subscribe for new episodes of Guyset every Tuesday, where we talk about the things guys are thinking about but don't always know where to ask.

See you next Tuesday!

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