9 Dating and Life Questions Every Guy in His 20s Is Thinking About (But Won't Ask Out Loud)

As a 25-year-old guy running a podcast called Guyset, I get asked a lot of questions that guys are genuinely wondering about but feel weird bringing up. These are the uncomfortable topics that make you think "I should probably already know this" or "where the hell am I supposed to find the answer to that?"

Recently, I tackled nine of the most common questions I receive, and I realized these are conversations we need to have more openly. So here's my honest take on the dating dilemmas, confidence struggles, and life situations that guys in their twenties are actually dealing with.

1. When Should You Text Her After Getting Her Number at the Bar?

The short answer: Next morning, before noon.

Look, if you're at a bar, chances are you've been drinking. You're not going to send your best message at 2 AM when you're three drinks deep. The exception? If the energy is absolutely electric and you're planning to meet up that same night, or you want to invite her to the next bar you're hitting with your friends.

For the real follow-up text - the "hey, it was great meeting you, want to grab drinks Thursday?" message - wait until the next morning when you're in your best mindset. She's hopefully thinking about you and excited about what you might text. Don't make her wait until 6 PM the next day for no reason. There's no game worth playing here.

Pro tip: When you first get her number, immediately text something like "Josh from [bar name]" so she has your contact and knows who's texting.

2. How to Tell Your Friend He Smells (And Why You Need to Do It ASAP)

This one's uncomfortable but necessary: you have to tell him immediately.

Your friend needs to know this information. He doesn't want to smell bad any more than you want him to. Maybe there's an underlying issue, maybe he's just forgetting deodorant, but either way, you're being a good friend by bringing it up.

Two approaches that work:

1. The direct route: "Dude, you need to know - you've got some body odor going on. Are you using deodorant?"

2. The softer approach: "Hey, I just got this new cologne that smells amazing. You should try it - my girlfriend said it's the best I've ever smelled."

Yes, it's awkward. Yes, he might be defensive in the moment. But he'll appreciate it later, and you're potentially saving him from embarrassing situations, especially with dating.

3. What's the Best Way for Girls to Flirt with Guys?

A girl actually sent this question in, and I have the simplest answer: just talk to us.

Seriously. That's it. Guys will take almost anything as flirting because we're not used to girls approaching us first. Say hi, laugh at our terrible jokes, touch our arm - we're simple creatures and we'll be thrilled that you're interested enough to start a conversation.

The bar for "flirting" with guys is incredibly low because it happens so rarely. Most guys will be like "Oh my god, she talked to me, she must like me." Which can be a problem too since we sometimes read into things that aren't there, but for girls wondering how to show interest - direct conversation works every time.

4. How Should You Feel About Your Girlfriend Reading Smut?

You should feel fine with it. Here's why: you're watching porn. Let's call it what it is.

Smut is basically sexually explicit literature - books that focus heavily on physical intimacy and explicit scenes between characters. It's her version of adult content, and there's nothing wrong with that.

If you're feeling weird or insecure about it, those feelings are normal when encountering something new. But think about it logically - she's reading, she's picking up books, she's intelligent. Maybe you could even read it together or use it as inspiration for your own relationship.

The bottom line: she enjoys it, it doesn't hurt anyone, and you have your own forms of adult entertainment. Don't make it weird.

5. How to Sound More Confident Instead of Insecure

Confidence comes down to two main things: body language and how you speak.

Body language basics:

• Stand up tall

• Put your shoulders back

• Stop slouching (yes, you're probably slouching right now)

Speaking with confidence:

• Cut the filler words

• Stop overthinking what you're about to say

• Tell the truth instead of trying to craft the "perfect" response

I recently heard author Elizabeth Gilbert speak, and she was incredibly confident because she simply told the truth. She said "I just say what I know to be true, and that's it." When you stop worrying about how others will perceive your words and just speak honestly, you naturally come across as more confident.

The key insight: What other people do with what you say isn't your responsibility. Your job is to say what you believe and know to be true.

6. When You Know "This Is It" with a Girl

You know when you're completely yourself around her. You're not thinking about how she'll perceive what you're about to say. You feel safe, comfortable, and genuinely happy when she's around.

Here are the real signs:

• You miss her when she's not there

• You see random things throughout the day that make you think of her

• When she walks in the door, you get butterflies because you're excited she's there

• You can't believe you're lucky enough to be with this person

• You want to share everything with her - good days, bad days, random thoughts

• When you're hugging her, everything feels right in the world

It doesn't have to be all of these feelings, but when you experience that sense of "I want this person to be part of everything in my life," that's usually when you know you're ready to move from casual to serious.

7. Little Things That Show You Care

These don't need to be complicated:

Simple gestures that matter:

• Get her flowers randomly (doesn't need to be a huge bouquet)

• Remember things she tells you and follow up on them later

• Use your phone's notes app to write down things she mentions wanting

• Compliment her genuinely ("you look beautiful," "I love your smile")

• Take pictures of things that remind you of her and send them

The notes app trick: When she mentions something she wants or likes, immediately put it in your notes. When her birthday or an anniversary comes up, you'll have a list of thoughtful gift ideas from months of listening.

Active listening: If she tells you about a difficult coworker on Monday, ask her how that situation is going the following week. She'll appreciate that you remembered and cared enough to check in.

8. It's Okay for Guys to Cry

I cried two days ago watching military homecoming videos on TikTok while on the toilet. I tear up watching Hamilton. I get emotional about random Instagram reels that hit me out of nowhere.

The reality: Everyone cries. Some people cry more than others, and some people don't admit it as much. Getting emotional means you're paying attention, you're present, and you're connecting with what's happening around you.

There's nothing wrong with being emotional or tearing up. It's part of being human, regardless of gender.

9. Drinking in Your 20s: Being Honest About It

Someone asked how often I drink, and I'll be honest: I drink what I consider a normal amount for a 25-year-old guy. Usually weekends (Friday, Saturday), sometimes Thursday, occasionally Wednesday or Tuesday depending on what's going on.

The important part: If you feel in control of your drinking, if it's not affecting your relationships, work, or mental health, you're probably fine. But if you're questioning whether your drinking has gotten out of control, that's worth paying attention to.

I actually did an episode (Episode 47) with my friend Brian who stopped drinking after college because he felt it was affecting his life negatively. It's worth listening to if you're wondering about your own relationship with alcohol.

The Point of These Conversations

Every single one of these questions, I've wondered about myself at some point. The reason I started talking about these topics is because there's nowhere else to find honest perspectives on the stuff guys in their twenties are actually thinking about.

These aren't definitive answers - they're my opinions based on my experiences. But I hope they help you feel less weird about wondering these things and less alone in not knowing where to find advice on topics that feel like you should already understand.

The bottom line: It's normal to have these questions. It's normal to feel uncertain about dating, relationships, confidence, and life in general when you're figuring things out in your twenties. The key is being willing to have these conversations and learn as you go.

Want to ask your own anonymous question? Head to guyset.com and hit "Ask Me Anything." These conversations happen because guys like you are brave enough to ask the questions we're all thinking about.