I am in no way a dating expert but I'm here to share what I’ve learned about going on first dates because this is an episode I wish I had heard myself. From texts I send before and after to what I wear and the questions I ask on the date, it’s all in here.

I hope you can take something from my experiences and the mindset I now have going into dating to prepare for your first dates.

The Complete First Date Guide for Guys: Mindset, Tips, and What Actually Matters

From the ask to the follow-up—everything you need to know about first dates that actually works

First dates. Just reading those two words probably made your palms a little sweaty, right? If you're like most guys in their twenties, the thought of asking someone out and then actually going through with it feels somewhere between terrifying and completely overwhelming.

Here's the thing: everyone makes first dates way more complicated than they need to be. I'm not claiming to be a dating expert—I'm just a guy who's been on some dates, some good, some terrible, and I've learned a few things along the way.

The Mindset That Changes Everything

Before we dive into what to wear or where to go, let's talk about the most important part: your mindset going into the date.

Stop thinking this person is going to be "the one."

If you walk into a first date thinking this could be your future spouse, you're setting yourself up for failure. You'll nitpick every little thing, looking for red flags or reasons why it won't work out. Every small quirk becomes a dealbreaker.

Instead, go in looking for a vibe.

Ask yourself: Is this someone I want to spend another evening with? Do I enjoy talking to them? Are they asking questions about me? Do I feel excited about seeing them again?

That's it. You're not trying to solve the rest of your life in two hours. You're just seeing if there's a connection worth exploring.

Part 1: The Ask (How to Actually Ask Someone Out)

Be Specific, Not Vague

Don't just say "Do you want to hang out sometime?" That turns into an endless back-and-forth of "I don't know, what do you want to do?"

Instead, try this: "Hey, I'd love to grab drinks with you. How's 7:30 this Tuesday at [specific wine bar/restaurant]?"

Or this approach: "Hey, would you want to grab drinks sometime this week?" Then follow up with: "How's Thursday at 7:30?"

Give them a concrete plan. It makes everything easier and shows you've put thought into it.

Part 2: The Follow-Up Text

Send a text the day of your date, around 2 PM if your date is at 7:30 PM.

Keep it simple:

• "Really excited to see you tonight!"

• "Looking forward to our date tonight"

• "Excited for tonight—see you soon!"

This serves three purposes:

1. Shows you're thinking about them

2. Confirms you're still on

3. Gives them time to let you know if something comes up

Part 3: Getting Ready (The Easy Part)

As guys, we have it ridiculously easy compared to what women go through getting ready. Our entire prep takes maybe 15 minutes:

• Shower

• Put on deodorant and cologne

• Maybe poop (seriously, get it out of the way)

• Brush your teeth or use mouthwash

• Put on actual pants (not sweatpants)

• Maybe shave if that's your thing

What to wear:

• Nice pants (not jeans if possible—they just look more put-together)

• A "fancy t-shirt" (basically a plain, well-fitting shirt without giant logos)

• Maybe a light jacket

• Belt that matches

• Clean sneakers or dress shoes

The goal is to look like you put in effort without overdressing. You want someone to look at you and think "yeah, he's clearly on a date."

Pro tip: If you have a sister, female friend, or even your mom available, send them a photo and ask "Does this work?" They'll tell you if you're clashing or if something looks off.

Part 4: Actually Being on the Date

Arrive Early

Be there 5-10 minutes before your date is supposed to start. While women are getting ready, doing their makeup, and probably talking to their friends about you, you literally took 15 minutes to get ready. The least you can do is be on time.

Plus, arriving early lets you:

• Scope out the menu so you don't panic-order

• Get a good table

• Relax before they arrive

Order What You Actually Want

Don't overthink what you're ordering. She's not going to think you're a psychopath for getting a gin and tonic. Just avoid anything that will make you gassy or uncomfortable.

Ask Questions (And Actually Listen)

Have some conversation starters ready:

• "What do you do? Do you like your job?"

• "Do you like your boss?"

• "What's your living situation like?"

• "Do you have siblings?"

• "What's your favorite restaurant you've been to recently?"

• "What would you bring to a deserted island?"

But don't treat it like a checklist. Let the conversation flow naturally and ask follow-up questions. You're not trying to learn their entire life story—you're just seeing if you vibe together.

Remember: This Isn't a Job Interview

You're not being judged on your performance. You're both just trying to figure out if you want to spend more time together. Stop obsessing over whether they like you and focus on whether you like them.

Part 5: After the Date

If it's going well and you've been at the same place for a while, you can suggest:

• "Want to grab another drink somewhere else?"

• "Should we take a walk?"

• "There's a cool bar around the corner if you're up for it"

Always offer to make sure they get home safely:

• Walk them to their Uber/cab

• Wait until they're actually in the car

• Ask them to text you when they get home

You don't need to call the Uber for them, but making sure they're safely on their way home is just basic decency.

Part 6: The Day After

If the date went well, text them the next day: "Hey, I had a really great time with you and would love to see you again. Are you free next Tuesday?"

Keep it simple and direct. You already set the precedent of being specific with your first ask, so now you can be a bit more conversational.

If the date didn't go well, still send a text: "Hey, I had a nice time getting to know you, but I don't see this going anywhere."

It's brief, honest, and way better than ghosting.

The Two Things That Will Ruin Your Date

1. Future Tripping

Stop thinking about what your kids will look like or whether their family will like you. You're literally on a first date with someone you didn't know 24 hours ago.

Future tripping is when you see the forest before the trees—overthinking so far ahead about a relationship that doesn't even exist yet.

Instead of thinking: "What if this doesn't work out? How will long-distance work if she's from California?"

Think: "Am I having fun right now? Do I want to see this person again next week?"

2. Treating It Like a Test

First dates aren't pass/fail situations. You're not being graded on your performance. If you don't click, that doesn't mean you failed—it just means you weren't a good match.

The Concept of Dating Karma

Here's something that's helped me reframe bad dates: dating karma. What goes around comes around.

How you treat people on dates—whether they go well or terribly—comes back to you. Being a decent human being, not ghosting people, and treating everyone with respect isn't just the right thing to do—it sets you up for better experiences down the line.

Bad dates aren't wasted time. They're learning experiences that help you figure out what you're looking for and make you better at dating overall.

The Bottom Line

First dates aren't supposed to be this massive, life-changing event. They're supposed to be fun. You're just trying to see if you want to grab dinner with this person next week.

Key reminders:

• Go in looking for a good vibe, not your soulmate

• Be specific when asking someone out

• Show up early and be present during the date

• Ask questions and actually listen to the answers

• Don't future trip or treat it like a job interview

• Be kind regardless of how it goes

If they don't like you, so what? Not everyone will, and not everyone has to. If you don't like them, that's fine too. You put yourself out there, met someone new, and learned something about what you're looking for.

The whole point is to live and learn, not to ace some test. Dating helps you figure out who you are, what you want, and how to be more confident putting yourself out there.

Final Thoughts

If you're going on a first date soon, try to adopt this mindset. Remember that the person across from you is probably just as nervous as you are. Be genuine, be kind, and focus on having a good time rather than impressing them.

Most importantly, don't let anxiety ruin what's supposed to be an enjoyable experience. You're young, you're figuring things out, and every date—good or bad—is helping you become a better version of yourself.

Want to hear the full conversation and Josh's complete first date breakdown? Listen to the complete episode of the Guyset podcast where Josh dives deeper into dating mindset, shares more specific examples, and discusses the concept of "dating karma" in detail. You can find it on Spotify, Apple Podcasts, or wherever you listen to podcasts.

Going on a first date soon? Remember: you're just seeing if you want to hang out again next week. Keep it simple, be yourself, and focus on having a good time. The rest will figure itself out.

Quick checklist for your next first date:

• ✓ Be specific when asking (day, time, place)

• ✓ Send a confirm text day-of

• ✓ Arrive 5-10 minutes early

• ✓ Order what you actually want

• ✓ Ask questions and listen to answers

• ✓ Make sure they get home safely

• ✓ Follow up the next day regardless of how it went

Related: Looking for outfit ideas or more specific tips? Check out our complete dating guides and style recommendations at guyset.com.

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Website: Guyset.com

Email: josh@guyset.com