Should you shave before a date? Is it okay to show up to a date in work clothes? When will you finally know what you want to do with your life?
In this Ask Me Anything episode of Guyset, I pull 10 real listener questions from my Spider-Man bucket hat and deliver honest and real advice for guys navigating their twenties. From dating anxiety to career setbacks, friendship changes to quarter-life crisis fears, these are the questions you've thought about but never knew who to ask.
Timestamps:
03:28: "Should I shave before my date?"
05:41: "Is it all right to show up on a first date in work clothes?"
08:02: "Is it bad if I'm a bad texter for dating?"
12:35: "A lot of my friends are moving and I'm feeling anxious about how far apart we're all going to be. I don't know if there's any advice for this, but I'm wondering if other people are feeling this way too."
19:44: "My girlfriend and I have been together for a year. What should I get her?"
22:07: "Should I keep a condom on me?"
24:18: "My recent review at work wasn't as good as I wanted it to be. What should I do?"
29:00: "When should I feel like I know what I want to do?"
33:44: "Any tips to help me get out of a slump? I'm feeling really lazy recently."
38:05: "When do you think a girl should start paying for dates?"
What You'll Learn:
Dating & Relationships: Pre-date grooming essentials, texting etiquette that actually works for dating, and perfect one-year anniversary ideas
Career Challenges: How to bounce back from bad performance reviews and turn criticism into career growth
Life Transitions: Dealing with friends moving away and the anxiety of post-college life changes
Personal Development: Morning routine hacks to beat laziness and build momentum
Real Talk: When you should actually know what you want to do (spoiler: probably not yet)
Perfect for: Guys in their twenties dealing with dating stress, career confusion, friendship changes, or general life anxiety. Also great for anyone who wants honest perspectives on modern masculinity and relationships.
Why This Episode Hits Different: It's 10 Questions Every Guy in His 20s Is Asking (But Won't Say Out Loud). This isn't your typical self-help podcast. I'm going through the exact same struggles as my listeners – quarter-life anxiety, career uncertainty, watching friend groups scatter. My advice comes from lived experience, not a textbook.
Subscribe to Guyset for weekly conversations about what should be talked about for guys in their twenties. New episodes every Tuesday.
Submit your questions for future Dear Guyset episodes:
- DM: @theguyset
- Email: josh@guyset.com
- Website: guyset.com
Connect with me:
- Instagram: @guysetpodcast
- TikTok: @theguyset
- Watch the full episode on YouTube: @guyset
- Website: guyset.com
- Email: josh@guyset.com
- Ask Me Anything: guyset.com
- Read my substack: guyset
See you next Tuesday!
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