I'm bringing back the anonymous question box format inspired by my high school sex ed class. This week, I'm pulling random questions from a hat that you guys asked and answering them completely unscripted.

Topics I cover:

• Dating advice: How to know when to end things vs. keep dating someone

• Reading relationship signals: Signs she's actually into you after 5 dates 

• Navigating weird conversations: The right way to talk about exclusivity without awkwardness

• Hookup etiquette: Do you have to stay over after hooking up? 

• Career advice: What to do when you feel like you can't impress your boss

• Dating app tips: Why Hinge isn't working and how I think you can fix it

• Moving in with your girlfriend: How I think you should split rent fairly

• Life hacks: Products that actually make your life easier 

• Dating profile advice: Setting up a dating profile that gets responses

• 
  

Submit your anonymous questions at Guyset.com - I can't see who sends them, so ask whatever you're really thinking about. No topic is off limits (as you can tell).

More on this episode:

Anonymous Dating and Life Advice for Men in Their 20s: Real Questions, Honest Answers

Navigating relationships, career challenges, and personal growth in your twenties can feel overwhelming. Here's practical advice from real anonymous questions submitted by guys just like you.

Introduction: The Power of Anonymous Questions

Remember those anonymous question boxes from high school health class? There's something powerful about being able to ask the questions you're really thinking without fear of judgment. That's exactly what inspired this collection of real-life advice for men navigating their twenties.

Dating and Relationship Advice

Should I Keep Dating Her or End Things?

One of the most common dilemmas young men face is knowing when to continue pursuing a relationship versus when to call it quits. Here's the honest truth: you probably already know the answer when you're asking this question.

Key takeaways:

• Give it 1-2 more dates to really understand your feelings

• Focus on whether you can be authentically yourself around this person

• Don't continue dating someone just because you think they like you

• The goal is finding someone who makes you feel like the best version of yourself

How to Know If She's Into You (5 Dates In)

If you've been on five dates with someone, chances are good that she likes you. People don't continue going on dates unless they're interested. The real question is: are you overthinking it?

Signs to look for:

• She's still texting you back consistently

• She seems excited about your dates

• Conversation flows naturally

• She's making time for you in her schedule

Pro tip: Don't spiral in your own head trying to analyze every interaction. Her actions will tell you everything you need to know.

When to Have "The Exclusive Talk"

Timing the exclusivity conversation doesn't have to be awkward. The key is being direct and honest about your intentions.

How to bring it up: "Hey, I'm not seeing anyone else right now and I don't want to. How do you feel about that? I really like you and enjoy spending time with you."

This approach is straightforward, non-threatening, and opens the door for honest communication.

Do You Have to Stay Over After Hooking Up?

Short answer: No, you don't have to stay over. But communication is everything.

Set expectations early by mentioning you need to head home that night or have early morning plans. This prevents awkward post-hookup conversations and ensures both parties are on the same page.

Life and Career Guidance

Feeling Like You Can't Impress Your Boss

This feeling is incredibly common and completely normal. Careers have natural ebbs and flows, and it's impossible to consistently impress your boss every single day.

What you can do:

• Ask proactive questions: "Is there anything else I can be doing for you?"

• Request feedback: "Is there any feedback you have for me?"

• End meetings by offering help: "Are there any other questions I can answer for you?"

• Remember that company priorities shift, and this affects how your work is perceived

Bottom line: Don't quit your job just because you're going through a rough patch. Have honest conversations about your performance instead.

Practical Life Tips

Products That Actually Make Life Easier

Sometimes it's the small things that make the biggest difference in your daily routine:

• Phone wallet case: Never lose your ID or credit cards again

• Grooming tools: Nose hair trimmers and body grooming equipment (yes, this matters more as you get older)

• Ice cube trays: Simple but effective for daily convenience

Moving in With Your Girlfriend: How to Split Rent

If you're making more money than your girlfriend, you should pay a higher percentage of the rent. This isn't just fair—it's practical.

Consider splitting costs 60/40 or 70/30 based on your income difference. This approach:

• Acknowledges your different financial situations

• Shows you're a considerate partner

• Allows you both to live in a nicer place than she could afford alone

Dating App Struggles: When Hinge Isn't Working

Dating app fatigue is real, and algorithm troubles can be frustrating. Here are three strategies to reset your dating app experience:

1. Take a break: Put the phone down for a week and reset mentally

2. Upgrade to premium: More visibility often leads to better matches

3. Complete profile overhaul: New photos, new prompts, fresh start

Remember: There are many ways to meet people outside of dating apps. Don't put all your eggs in one digital basket.

Setting Up an Effective Dating Profile

Your dating profile should showcase the real you, not the person you think others want to see.

Essential elements:

• Photos that show different aspects of your personality

• Prompts that invite conversation and responses

• Authentic representation of your interests and humor

• Avoid anything too controversial or political initially

Key principle: Make every prompt something someone can easily respond to. If people can't start a conversation based on your profile, you're missing opportunities.

Final Thoughts: Trust Your Instincts

Whether you're navigating a new relationship, dealing with career uncertainty, or just trying to figure out adult life, remember that you often know the right answer already. Sometimes we just need permission to trust our instincts.

The twenties are a time of exploration and growth. Don't rush to have everything figured out, but also don't be afraid to make decisions when something isn't working. There's time to course-correct, learn, and grow.

Listen to the Full Episode

Want to hear Josh's complete thoughts and additional insights? This blog post is based on a full episode of Guyset: A Guy's Guide to What Should Be Talked About - a weekly podcast covering everything men in their 20s and 30s need to discuss.

Where to listen:

• Website: guyset.com

• Apple Podcasts: Search "Guyset"

• Spotify: Available on all major podcast platforms

• YouTube: Full video episodes available

New episodes drop every Tuesday with fresh topics, guest interviews, and more anonymous Q&A sessions like this one.

Want to submit your own anonymous question? Visit guyset.com and use the submission form - you can literally write whatever you want for your email address. All questions remain completely anonymous.

These insights come from real anonymous questions submitted by men in their twenties navigating relationships, careers, and personal growth. Remember: you're not alone in facing these challenges, and it's okay to seek advice and guidance as you figure things out.

New episodes drop every Tuesday with dating advice, relationship tips, career guidance, and honest conversations about what guys in their 20s are actually wondering about.

If something I said helped you out, leave a 5-star review and share it with a friend who needs to hear this advice.

Connect with me:

• Instagram: @theguyset

• TikTok: @theguyset

• Watch the full episode on YouTube: @guyset

• Website: guyset.com

• Email: josh@guyset.com

• Read my substack: guyset

• Ask Me Anything: guyset.com

See you guys next Tuesday.