This episode is your comprehensive guide to going on a first date. I talk about everything from what to say in the text asking to go out and picking a day and time to hyping yourself up before, what to wear, and what to talk about on the date (this is what I was most worried about when first going on dates).

When I first thought of the idea for this podcast, this was one of the big topics I was looking for and couldn't find. I wanted to hear more advice and real perspectives from guys in their 20s about dating and relationships and I'm so excited that I feel confident enough to share my perspective on it now after a year of giving it a shot. As dumb as it sounds, I'm proud of this one and hope you take some good things away from it.

This episode is really detailed and goes deep into a lot of different topics around a first date so check out the time stamps below if you're only interested in certain topics. I can almost guarantee there's going to be at least one thing in this episode for you if you're currently dating, going on dates, or thinking about starting soon (or just want to learn more and hear about dating in your 20s).

The Ultimate First Date Guide for Guys: From Planning to Follow-Up

Everything you need to know to nail your first date - from what to wear to what to talk about.

The Mindset That Makes All the Difference

Before we dive into logistics, let's talk about the most important part: your headspace going into the date.

Don't Google stalk them beforehand. Seriously. Don't check out their social media profiles, research their siblings, or investigate where they work. Go in with an open mind instead of preconceived notions about whether they're "too smart," "too successful," or any other comparison that'll psych you out.

Half the battle is how you're feeling before the date. If you think it's going to go badly, it probably will (hello, self-fulfilling prophecy). If you're excited about the possibility, you're already ahead of half the people going on first dates.

Think of it as a new experience - a chance to learn something about yourself, discover a new place, or at minimum, get a good story to share with friends.

When to Schedule Your First Date

Always choose a weeknight. Here's why:

• Less pressure than weekend dates

• Reserve weekends for friends and activities you know you'll enjoy

• If it goes poorly, at least you didn't waste your Friday or Saturday

• If it goes well, weekend dates become more special for round two

Best days: Wednesday or Thursday nights work perfectly. Tuesday is fine too, but avoid Mondays (everyone's tired and cranky).

Where to Go: Keep It Simple, Keep It Casual

Drinks are the golden standard for first dates:

• Easy to suggest via text: "Hey, want to grab drinks Thursday at 7:30 at [place]?"

• Low pressure - if it's not going well, you finish one drink and you're done

• If it is going well, you can always order another round

• Much more affordable than dinner (which can easily cost $70+ for two people)

Alternative options that work:

• Coffee dates (great for afternoon meetings)

• Activity dates like mini golf or bowling

• "Cookie tour" - walking to different dessert spots to compare

• Museum or art gallery visits (walking and talking)

Avoid: Movies (you can't talk), formal dinners (too much pressure), walks in the park (can seem weird)

How to Ask Them Out (With Confidence)

Be specific and confident in your ask. Instead of: "Would you want to do drinks or bowling or maybe sushi this week?"

Try: "Hey Anna, how's bowling Thursday night at 7:30?"

This shows confidence and decisiveness - you know what you want and you're not the guy who can't choose between pizza and sushi.

Pre-Date Prep: Setting Yourself Up for Success

Maintaining Energy After Work

• Don't nap or crash on the couch

• Walk home instead of taking transit

• Put on upbeat music to maintain energy

• Remember: most first dates are at 7 or 7:30, so you don't have much downtime

The Pre-Date Ritual

Have a drink to calm nerves: A beer or small shot can help ease anxiety (but don't overdo it)

Create a pump-up playlist: Songs that get you excited and confident. Whatever gets you hyped works.

Get your roommate's opinion: If possible, run your outfit by someone for a quick confidence boost

What to Wear: The Foolproof Formula

The can't-go-wrong combo:

• Button-down shirt (navy or white work great)

• Chinos or dark jeans

• Clean white sneakers or casual shoes

• Don't button the shirt all the way up - leave a couple undone

Final touches:

• Shave if you have time (looks like you put in effort)

• Cologne and deodorant

• Chew gum on the way (even if it makes your drink taste weird, your breath will be fresh)

Date Day Logistics

Arrive 5-10 minutes early - but not so early you're sitting there anxiously waiting

Stay off your phone while waiting - be present and aware of when they arrive

Expect them to be 10-15 minutes late (just being honest about typical experiences)

What to Talk About (Because Conversation Doesn't Have to Be Scary)

Safe and Engaging Topics:

• The area they live in

• Their job (and yours)

• Roommate situations

• Favorite restaurants in the city

• Bars they like

• TV shows, movies, music, podcasts

• Recent books they've read

Topics to Avoid:

• Politics

• Controversial subjects

• Ex-relationships

• Anything that could stir the pot

Pro tip: Come prepared with something recent you've watched or read, but don't force the conversation - let it flow naturally.

After the Date: The Follow-Up Strategy

If it went well:

Send a text either that night (around 11 PM) or the next morning: "Hey, I had a really great time with you tonight. Would love to see you again."

Then follow up with a specific suggestion: "How's 7:30 next Thursday at that sushi place you mentioned?"

If it didn't go well:

Still send a polite text the next day: "Hey, it was really nice to meet you, but I don't see this going any further. I wish you all the best."

The in-between texting:

Keep it light and don't feel pressured to maintain constant conversation. It's okay to wait until the second date to really get to know each other better.

Mindset Shifts That Change Everything

From "Does she like me?" to "Do I like her?" - Remember, you're evaluating the connection too, not just hoping for approval.

Stay present - Don't get ahead of yourself planning the next three dates or thinking about the future. You just met.

Take it date by date - Even great first dates don't always lead to second dates, and that's okay.

The Rejection Reality Check

Here's the truth: You will get rejected sometimes. You will have dates that don't go well. That's part of the process, not a reflection of your worth.

The worst that happens? They say no or the date doesn't work out. The best that happens? You have a great time and build confidence for putting yourself out there.

Remember: There are so many opportunities out there. One "no" or one awkward date doesn't define your dating life.

The Bottom Line

Going on first dates should be exciting, not terrifying. When you approach them with the right mindset - open, confident, and realistic - you set yourself up for success regardless of the outcome.

You're not just trying to impress them; you're seeing if there's mutual compatibility. That takes the pressure off and makes the whole experience more enjoyable.

Most importantly: If you don't ask, you'll never know. The only way to get better at dating is to actually go on dates. So take the shot, learn from each experience, and remember that confidence comes from practice.

Want more honest dating advice and tips for guys in their 20s? This comprehensive guide comes from the Guyset podcast, where no topic is off-limits. Listen to the full first date episode and more at guyset.com or wherever you get your podcasts.

Have your own dating questions or want to share first date tips? Reach out at advice@guyset.com - your experiences help the whole community.

Timestamps 

1:53 Mindset going into a first date

4:55 Picking a day for the first date

5:53 Where to go/ what to do on the first date

9:58  How should I ask someone out

10:45 How to stay hyped up after a long day

11:55 Having a drink before a first date

13:52 Hype up music before

14:32 What to wear for a first date

16:47 How early should I get there

17:31 What time should I make the date

18:41 Topics to talk about on a first date

20:56 When to follow up after the date/ what to say

23:49 Mindset after the first date

25:34 More thoughts for you

Thanks for listening! Let me know what you think and what advice you have for me on this topic that I can share with the rest of the community.

Send in any questions, things you want me to talk about, or things that should be talked about for guys in their 20s to josh@guyset.com  

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See you next Friday.