Guys constantly have questions, worries, and anxieties that they don’t know where to find the answers and also don’t want to ask in fear of looking insecure, not confident, vulnerable, or weak, so I’m here to reveal those questions and answer them to the best of my ability. Maybe you can bring some of the advice I share and a different perspective back to your question, worry, or anxiety.

Dear Guyset: Real Answers to the Questions Guys Actually Ask

Introducing our new Q&A series where we tackle the anxieties, worries, and everyday questions guys have but don't know where to find answers

Guys have questions. Lots of them. But here's the thing – we keep those questions buried deep down, afraid of being seen as weak or not confident enough. The reality? We all have the same worries, anxieties, and uncertainties. We just don't talk about them.

That's exactly why we're bringing back our Q&A series with a new name: Dear Guyset. This is your space to get real answers to real questions from someone who's figuring it out alongside you.

Why "Dear Guyset" Exists

The truth is, there's nowhere else to get honest answers to the specific questions guys in their 20s actually have. Reddit forums are chaotic and impossible to search. Traditional men's publications focus on celebrities and luxury products that don't relate to your actual life.

We created Dear Guyset because you deserve a place to find advice on everything from dating anxieties to career moves to basic life questions – all without judgment and with the understanding that asking questions is actually a sign of strength, not weakness.

Submit your questions to: dearguyset@gmail.com

This Week's Questions & Answers

"Why is dating so hard right now?"

This question has probably existed in every decade, but right now it feels particularly challenging for two main reasons:

1. Fear of rejection keeps us paralyzed. We're so afraid of being turned down that we don't put ourselves out there. Whether it's approaching someone at a bar or even just messaging people on dating apps, the fear of hearing "no" stops us from trying.

The only way to get better at handling rejection is to face it. That means shooting your shot even when you're not sure about the outcome. Remember: rejection isn't a reflection of your worth – it's just part of the process.

2. We don't give connections enough time to develop. Dating apps have created a "swipe left, swipe right" mentality where we're quick to move on if someone isn't perfect immediately. We think there's always someone better just one swipe away.

The reality is that real connections take time. Instead of looking for instant perfection, give people (and yourself) a chance to see if something genuine can develop over multiple dates.

"I've been on five dates with this girl and Valentine's Day is coming up. Should I get her something?"

Five dates is definitely in the territory where you're invested in this person. Here's what to do:

Ask her to be your Valentine. You don't have to make it official or rush into a relationship, but after five dates, asking "Would you be my Valentine?" is totally appropriate.

Get her flowers. A bouquet shows thoughtfulness without being overwhelming. It acknowledges the day without putting pressure on defining the relationship.

Don't force the relationship conversation. Valentine's Day doesn't mean you need to immediately become official. Make sure you're genuinely ready for that step before taking it.

"How do I stop getting pissed off at my coworker?"

Workplace relationships are tricky, and here's the hard truth: you're not at work to make friends. You're there to build a career and be successful.

Reframe their behavior. When a coworker is being difficult, it's usually a reflection of their insecurities, jealousy, or lack of confidence – not something you did wrong.

Accept that not everyone will like you. If you're doing great work and being successful, some people might resent that. It's an unfortunate reality of workplace dynamics.

Focus on your performance, not their attitude. Don't let their negativity hold you back from doing your best work. Take the high road while protecting your own interests.

"Do you have any tips for focusing better at work?"

The biggest productivity killer is also the most obvious one: your phone.

Put your phone face down or in another room during meetings and focused work time. Our tendency to check notifications, scroll social media, or respond to texts completely destroys our ability to be present.

Take notes during meetings. Having a notepad and pen forces you to actively listen and engage with what's being discussed. Even if you don't reference the notes later, the act of taking them keeps you focused.

Set boundaries with yourself. Decide on specific times when you'll check your phone, and stick to those boundaries.

"How do I ask for a raise?"

Come prepared with concrete examples of the value you've brought to the company. This is the most important part of the conversation.

Document your contributions. List specific projects you've led, problems you've solved, or ways you've directly contributed to company revenue or efficiency.

Tell a story about your impact. For example: "I led the project that increased our lead volume by 30%, which directly resulted in $X in new sales."

Time it strategically. Performance review periods are natural times to have this conversation, but don't wait if you have a strong case for why you deserve more compensation.

Be specific about what you want. Don't just ask for "more money" – research market rates and have a specific number in mind.

"How do I tell my friend to be more confident?"

You can't just tell someone to "be more confident," but you can help them get there.

Share your own experiences. Say something like: "I know how that feels. I've been there before when [specific example]. I got through it by [specific action]."

Normalize their struggle. Let them know they're not alone: "You're not the only person who's ever felt this way. We all go through this."

Offer perspective without being preachy. Instead of "just be confident," try "I know this feels terrible right now, but staying down isn't going to help. What if we [specific suggestion]?"

Give them a reality check with love. Sometimes friends need to hear: "You can feel sorry for yourself for a bit, but at some point you need to get back out there because amazing things might be waiting."

"How do I stop overthinking?"

As a recovering overthinker, here's what actually works:

Notice when you're creating scenarios that don't exist. Most overthinking involves worrying about things that might happen, could happen, but probably never will happen.

Use the cloud visualization technique. When you catch yourself overthinking, imagine putting that thought on a cloud in your mind and watching it float away. This helps you mentally release thoughts that aren't serving you.

Remember the phrase "cross that bridge when you get there." Don't spend today worrying about a problem that might happen next week, next month, or never.

Take a mental note of how far down the rabbit hole you go. Sometimes just recognizing how deep into overthinking you've gotten is enough to snap you out of it.

The Common Thread

Every question we received has something in common: they're all normal human experiences that we think we're alone in having. The anxiety about dating, workplace frustrations, wanting to help friends, struggling with focus – these aren't character flaws or signs of weakness. They're part of being human.

The difference between guys who seem to have it all figured out and those who don't isn't that some people don't have these worries. It's that some people have learned to talk about them, seek advice, and work through them instead of keeping them buried.

What's Next

We'll be doing Dear Guyset episodes whenever enough questions pile up, and every single question will also get a dedicated blog post on guyset.com where you can find more detailed advice.

The goal isn't to have all the answers – it's to create a space where asking questions is normalized and where you can find perspectives from someone who's going through the same things you are.

Your questions matter. Whether it's about relationships, career moves, friendship dynamics, mental health, or even something as specific as "what shampoo should I use?" – if you're wondering about it, chances are other guys are too.

Keep the Questions Coming

Submit anything you're curious about, worried about, or just need another perspective on to dearguyset@gmail.com.

No question is too small, too specific, or too "obvious." If you're thinking about it, it's worth addressing.

Remember: asking questions isn't a sign of weakness – it's a sign that you're actively working to improve your life. And that's exactly what we're here for.

Want more real talk about the stuff guys actually think about?

Listen to Guyset: New episodes every Tuesday tackling everything guys wonder about but don't know where to find answers

Get daily advice: Visit guyset.com for organized, searchable answers to hundreds of questions

Submit your questions:

• Email: dearguyset@gmail.com

• DMs: @theguyset on all social platforms

• Anonymous submissions: Available on guyset.com

Your question could be featured in the next Dear Guyset episode – and help another guy who's wondering about the exact same thing.

Send any questions to: dearguyset@gmail.com or DM @theguyset 

5:14 Dear Guyset why is dating so hard right now?

13:02 Dear Guyset I’ve been on 5 dates with this girl and Valentine’s Day is this week, should I get her something?

15:47 Dear Guyset how do I stop getting pissed off at my coworker?

20:28 Dear Guyset do you have any tips for focusing better at work?

23:03 Dear Guyset how do I ask for a raise?

26:56 Dear Guyset What are you reading?

29:19 Dear Guyset what shampoo do you use?

31:22 Dear Guyset how do I help my friend?

33:52 Dear Guyset how do I tell my friend to be more confident?

40:06 Dear Guyset how do I stop overthinking?

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See you guys next Tuesday.