Valentine's Day comes with pressure for almost every guy, whether you're single, in a relationship, or somewhere in between.

I've experienced Valentine's Day from both sides. I've been single for most of my life, and I've also been in relationships. And I can honestly say they're completely different experiences, but they're both stressful in their own way.

If you're single, Valentine's Day can feel like a reminder of what you don't have. If you're in a relationship, it can feel like pressure to get everything right. And when Valentine's Day falls on a weekend, that pressure feels even heavier.

In this episode, I talk about why Valentine's Day brings up so much for guys and how to take the pressure off without ignoring how you actually feel. I break down the mindset behind the holiday, how social media makes it worse, and why this one day can make you question where you're at in your life or dating life.

For single guys, I share how to get through Valentine's Day without spiraling, doom-scrolling, or forcing something that doesn't feel right, and how to reframe the day in a way that actually helps you move forward.

For guys in relationships, I talk through simple, realistic ways to show effort and care without stressing yourself out or overcomplicating the day, and what actually matters versus what doesn't.

This episode is about easing pressure, reframing expectations, and remembering that wanting love, connection, or something more is normal and not something to beat yourself up over.

If Valentine's Day makes you feel anxious, frustrated, lonely, or just a little off, this episode is here to make it feel lighter.

Timestamps

00:00 – Why Valentine's Day feels heavier
01:15 – The pressure every guy feels
02:35 – Why it hits single guys harder
05:45 – What not to do when you're single
10:30 – Reframing Valentine's Day

15:30 – Pressure in relationships
18:10 – What actually matters
21:20 – Simple ways to do it right

26:10 – Taking the pressure off
29:10 – Final thoughts

Watch the full episode on YouTube: @guyset

Instagram: @guysetpodcast

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

Daily blog posts: https://guyset.com/

See you next Tuesday!

Most guys are not bad at flirting. They are just stuck in their head.

In this episode of Guyset, I go back to the basics with Flirting 101. I talk about how to flirt with confidence, how to make the first move without getting stuck in your head, and how to handle rejection without letting it destroy your self-esteem. This is not about pickup lines or dating tricks. It is about mindset, presence, and learning how to put yourself out there in a way that feels natural.

I share real stories from my own dating life, including moments where flirting went wrong, confidence took a hit, and I had to learn how to try again. If you feel nervous talking to women, struggle with fear of rejection, or replay conversations in your head after the fact, this episode is for you.

Whether you are just starting out with dating, getting back into it after a breakup, or trying to feel more confident flirting in real life, this episode breaks down the fundamentals in a simple and honest way.

In this episode, I cover:

• How to flirt without overthinking
• How to make the first move with confidence
• How to read interest and body language
• How to deal with rejection and keep going
• Why flirting is a skill you build through reps, not something you are born knowing

This is a foundational episode for guys who want flirting to feel easier, calmer, and more natural.

Timestamps:

00:00 Why flirting still matters for every guy
01:55 Flirting 101 and why we are going back to the basics
04:10 Why fear of rejection holds most guys back
07:00 A real flirting story that did not go well
11:20 How overanalyzing kills confidence
14:45 Stop beating yourself up for awkward moments
17:30 How to get out of your head before you flirt
20:15 Body language, eye contact, and presence
23:10 What to actually say when you walk up to someone
25:00 Asking for her number and making the first move
27:40 When to move on instead of forcing it
30:00 Why flirting is a skill you build through reps

If this episode helped in any way, I would really appreciate it if you subscribed, gave it five stars, and left a quick review. It genuinely helps more guys find the show.

You can watch the full episode on YouTube at @guyset
You can follow me on Instagram and TikTok at @guysetpodcast

If you have something you want me to talk about, head to https://guyset.com/ask-me-anything and send it in.
I also write daily blog posts on dating, confidence, mindset, and life in your 20s at https://guyset.com/

See you guys next Tuesday!

Feeling behind in life is one of the most common thoughts people have in their 20s, especially after college. You look around and it feels like everyone else is moving faster. Better jobs. Better relationships. More clarity. More progress. And somehow you missed the timeline.

In this episode, I break down why that feeling exists, why it's so convincing, and why it's also misleading.

We talk about comparison, social timelines, career pressure, relationships, and the unspoken belief that life is supposed to follow a specific order by a specific age. I explain why there is no universal timeline, why no one is actually ahead, and how most people's lives look a lot more similar than we think once you zoom out.

I share two visuals that completely changed how I think about being "behind":
– The idea that we're all walking different tightropes, moving at different speeds
– The idea that everyone builds their life like a puzzle, starting in different places

This episode is for anyone who has ever asked:

Am I behind in life?
Why does everyone else seem to have it figured out?
Is it normal to feel lost in your 20s?
Am I running out of time?
Why does comparison feel so heavy right now?

If you've been feeling stuck, late, or unsure if you're doing life "right," this conversation is meant to help you zoom out, reset your perspective, and stop measuring your life against someone else's timeline.

There is no behind. There are just different chapters, different seasons, and different moments of change.

If this resonated, subscribe for more honest conversations about confidence, dating, and figuring things out.

Watch the full episode on YouTube:
@guyset

Follow Guyset on Instagram:
@guysetpodcast

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

Read daily blog posts:
https://guyset.com/

See you guys next Tuesday.

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!

How do you become more interesting, especially on dates, at work, or when you feel stuck in your 20s?

This episode started with a simple question I was asked about dating: How do I become more interesting? But the more I thought about it, the more I realized this question applies to everything. Confidence. Career. Friendships. Relationships. How you see yourself when life starts to feel repetitive or stagnant.

In this episode, I break down why feeling uninteresting is rarely about your personality and almost always about not trying new things. When you stop experimenting, confidence fades. Conversations feel flat. Dates feel harder. Life starts to feel smaller than it should.

I talk about why experimentation matters more than talent, why being willing to look bad at something is actually a strength, and how trying new things naturally makes you more confident, more attractive, and more grounded. Not because you are performing for other people, but because you are finally engaging with your own interests again.

We get into ambition, hobbies, and why people are drawn to passion even when it is messy. Becoming more interesting is not about impressing others. It is about having something you are genuinely excited to talk about.

In this episode, I cover:

• How to become more interesting without changing who you are

• Why confidence drops when you stop trying new things

• What actually makes someone attractive on dates

• How hobbies and curiosity change how you show up

• Why experimentation matters more than talent

If you have ever searched how do I become more interesting, why do I feel boring, or how to be more confident on dates, this episode is for you.

The goal is not to find your forever passion.
The goal is to start trying again.

Subscribe, give this episode 5 stars, and leave a review!

Ask me anything: @guysetpodcast & https://guyset.com/ask-me-anything

Watch the full episode on YouTube: @guyset

Instagram: @guysetpodcast

Daily blog posts: https://guyset.com/

TikTok: @theguyset

Email: josh@guyset.com

See you guys next Tuesday!

There's a moment that hits after work when you sit in your car, open LinkedIn, or scroll job boards and think, what am I actually doing? Not because you're failing. Not because things are falling apart. But because something just doesn't feel right.

In this episode, I talk honestly about career uncertainty, burnout, comparison, and the pressure to feel fulfilled by your job. I share the thoughts I've been sitting with over the past year, the conversations I've had with coworkers and friends at very different stages of their careers, and why realizing that no one really has it all figured out can be strangely comforting.

If you feel lost in your career, unsure about your next step, or questioning whether you're on the right path, this episode will help you feel less alone.

This isn't an episode with a perfect roadmap or a five-step plan. It's about feeling seen in the middle. About understanding that not knowing what you want to do doesn't mean you're behind. It means you're paying attention.

Timestamps

00:00 – Welcome to Guyset and why this episode matters
00:45 – The after-work feeling of "what am I doing with my career?"
02:40 – Questioning fulfillment, purpose, and whether your job should feel meaningful
04:55 – Burnout, bad days at work, and starting to look for something else
06:15 – How LinkedIn comparison makes career uncertainty louder
08:05 – The parts of career struggle no one posts about
09:40 – Realizing career uncertainty doesn't disappear with age
11:10 – Conversations with older coworkers who still feel unsure
12:45 – Why not having it figured out doesn't mean you're failing
14:10 – Talking to people as the best way to navigate uncertainty
15:55 – Why reaching out to others actually works
17:05 – Identifying what you're good at vs. what you enjoy
18:45 – Narrowing your career focus instead of searching broadly
20:35 – Following your gut even when it's uncomfortable
22:10 – Why it's easier to stay put than face the unknown
23:45 – Reframing uncertainty as a normal part of growth
25:10 – Final thoughts on comparison, confidence, and being okay where you are

Subscribe, give this episode 5 stars, and leave a review!

Watch the full episode on YouTube: @guyset

Instagram: @guysetpodcast

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

Daily blog posts: https://guyset.com/

TikTok: @theguyset

Email: josh@guyset.com

See you guys next Tuesday!

Every year, we tell ourselves this is the year we finally change things.

We reset on January 1st. We make big promises. We swear this time will be different. And then life happens. A day gets missed. A habit slips. Motivation fades. And suddenly the goal that mattered so much feels heavy, frustrating, or out of reach.

In this episode, I break down how to actually make your New Year's resolutions stick, even when life gets in the way.

This isn't about discipline, motivation, or forcing yourself to be perfect. It's about building goals that can survive missed days, busy weeks, and real life. I talk about why the "fresh start" mindset sets so many guys up to quit, why missing a day doesn't erase your progress, and how to break big goals into simple systems you can return to again and again.

You don't need a perfect reset.
You don't need to start over.
You just need a way to keep going.

Timestamps

00:00 – Why we treat New Year's like a "reset button"
01:30 – The pressure we put on January 1st
03:00 – Why life doesn't actually change when the calendar does
05:00 – How missing one day turns into quitting altogether
07:10 – There is no grand reset and why that matters
09:30 – The brushing your teeth mindset for goals
11:45 – Why missing a day doesn't erase your progress
14:00 – How I think about goals like reading a book
16:15 – My simple framework for setting goals
18:30 – Breaking big goals into smaller systems
20:45 – My personal fitness goal and how I structure it
23:00 – Why consistency matters more than perfection
25:20 – How to keep going when motivation fades
27:00 – Final thoughts and how to apply this anytime during the year

Subscribe, give this episode 5 stars, and leave a review:

• Watch the full episode on YouTube: @guyset
• Instagram: @guysetpodcast
• Ask Me Anything: https://guyset.com/ask-me-anything
• Daily blog posts: https://guyset.com/
• TikTok: @theguyset
• Email: josh@guyset.com

See you guys next Tuesday!

Almost 50% of guys ages 18–25 have never asked someone out in person.
Not because they do not want to, but because they hesitate.

In this episode of Guyset, I break down why asking someone out feels so nerve-wracking now, where the fear actually comes from, and why the usual advice like "just shoot your shot" does not help when you are in your head.

I talk about dating anxiety, fear of rejection, confidence, and the shame loop that keeps guys frozen instead of moving. I share my own experiences, the mindset shift that helped me stop overthinking, and a way to reframe fear so it stops running the show.

If you have ever wanted to ask someone out but talked yourself out of it, replayed the moment on the way home, or felt like everyone else has it figured out except you, this episode is for you.

New episodes every Tuesday answering the questions guys are actually asking.

Timestamps:

00:00 Welcome to Guyset
00:18 The statistic that explains why dating feels harder now
01:30 Why so many guys avoid asking someone out in person
02:20 The shame loop that keeps you stuck
03:50 Fear of rejection vs fear of confirming what you already believe
05:00 Why asking someone out feels so high-stakes
06:40 Cuffing season pressure and feeling behind
08:20 Why "just go for it" advice does not work
10:30 What rejection actually does to your confidence
12:55 The regret of not saying anything
14:40 How my perspective on confidence has changed
16:50 Reframing fear into excitement
18:20 The "fear vs potential" mindset
23:05 Why potential is more powerful than trying
26:25 Getting out of your head and into action
28:35 Realizing you are not the only one feeling this way
30:10 How you put yourself in the other 50%
31:45 Final takeaway

Subscribe, give this episode 5 stars, and leave a review!

• Watch the full episode on YouTube: @guyset
• Instagram: @guysetpodcast
• Ask Me Anything: https://guyset.com/ask-me-anything
• Daily blog posts: https://guyset.com/
• TikTok: @theguyset
• Email: josh@guyset.com

See you guys next Tuesday!