One of the biggest constants and things in common for guys in their 20s and 30s is we are all planning dates. Figuring out what to do or where to go on a date just adds to the anxiety and stress of dating so in this episode I share a guide for what to do on the first through the 5th date, tell you about the dates I've gone on, and give advice, recommendations, and notes for each date along the way.

The Complete Guide to Date Nights: From First Date Nerves to Relationship Planning

Originally featured on the Guyset podcast - your guide to what should be talked about

Why Dating Advice Matters for Every Guy

Whether you're swiping on dating apps, planning your first date in months, or trying to keep the spark alive in a relationship, date planning is one of the most constant challenges we face in our twenties and beyond.

The reality: Everyone is either currently going on dates, wanting to go on dates, or planning date nights with their significant other. This makes dating advice universally relevant - whether you're single, in a situationship, or in a committed relationship.

A New Perspective: Dating Advice from Someone in a Relationship

After over a year of sharing single dating experiences, here's a fresh perspective from someone who's been in a relationship for about a month and a half. The pressure of date night doesn't disappear when you become official - it just changes form.

Gone are the worries about:

• Will she text me back?

• Should I go for the kiss?

• When do I send the follow-up text?

But the challenge of planning meaningful dates and maintaining good communication remains just as important.

The First Date Foundation

The Golden Rule: Comfort Equals Confidence

The best first date location is wherever YOU feel most comfortable and confident. This isn't about impressing someone with fancy venues - it's about creating the right setting for authentic conversation.

Top first date recommendations:

• Drinks/Wine: Easy 2-glass timeframe, casual setting, not crazy expensive

• Ice cream or coffee: Perfect for non-drinkers

• Appetizers and drinks: More casual than full dinner, easier decision-making

Why I Avoid Dinner on First Dates

Full dinner dates create unnecessary complications:

• You don't know their food preferences yet

• Questions about splitting appetizers and paying become awkward

• It's a bigger time and financial commitment before you know if there's chemistry

Remember: The activity is just a backdrop for conversation. The goal is getting to know each other, not creating Instagram-worthy moments.

A Real First Date Story

I planned to take someone for margaritas and guacamole after learning she loved Mexican food. The restaurant was closed when we arrived. We ended up at a Spanish tapas place getting croquettes and sangria - completely not my ideal first date setting.

The result: It became a funny shared story we still reference. Sometimes the "failed" dates make the best memories because they test how well you both handle unexpected situations.

Managing First Date Nerves

Here's the truth: You're going to be nervous on every first date, and that's completely normal.

Think of dating like going to the gym. When you start lifting weights, everything feels incredibly heavy. You look around wondering how everyone else makes it look so easy. With more reps, the weights are still heavy, but you get stronger and more capable of handling them.

Dating works the same way. You'll still feel nerves, but with more experience, you know what to expect and how to handle those feelings.

The Kiss Question: Trust Your Gut

The biggest question guys have: Should I go for the kiss at the end of the date?

My advice: You have to trust your gut and read the vibe. If you're feeling it's right, it probably is. If you have lots of doubt and anxiety about it, it's probably not the right moment.

Important reminder: Not every date needs to end with a fairytale sidewalk kiss. It's okay to take it slow and let things progress naturally.

Second Date Strategy

Listen and Build

The best way to plan a second date is to listen to what they mentioned during your first conversation. If you blanked out due to nerves (totally normal), you can casually ask about preferences over text:

• "What's your favorite type of wine?"

• "Do you prefer Italian or Mexican food?"

• "What kind of places do you like to hang out?"

Then be decisive. Pick something and stick with it. Don't overthink it.

Example: Building on First Date Conversation

After discussing that we both loved white wine on our first date, the second date was at a wine bar during happy hour. Simple, based on shared interest, and budget-friendly.

The Third Date Turning Point

Why the third date matters: This is often when you start deciding whether you want to continue seeing this person seriously.

You don't need to rush this decision, but it's generally around dates 3-4 when things start feeling more serious or you realize it's not going anywhere.

Setting Considerations

By now you know them better, so you can:

• Plan based on things you've learned about their interests

• Consider dinner if you're ready for that level of commitment (time and cost)

• Stick with the same format (drinks/appetizers) if that's working

The key: You're probably more comfortable now, so choose settings that reflect that growing comfort level.

The Fourth and Fifth Date Evolution

Time for Real Conversations

This is when you should consider having mature conversations about where things are heading. Not necessarily "what are we?" but more like:

"I'm really enjoying spending time with you. How are you feeling about everything?"

This conversation is awkward and difficult, but it's an important stepping stone in any developing relationship.

Great Date Ideas for This Stage

Dinner and a movie: You're comfortable sitting in silence together now

Cooking at home: Either you cook for them, they cook for you, or you order takeout and watch TV. This is the "next level unlocked" - showing them the real you in your natural environment.

Concerts or shows: These work better when you really know the person and are comfortable spending extended time together

The At-Home Date Milestone

Bringing someone to your apartment represents showing them the real you:

• Your actual living situation (roommates and all)

• How you operate in your natural environment

• Your authentic self without the "date performance"

This vulnerability is important because healthy relationships require both people to be entirely themselves.

Advanced Date Planning: Months 2+

Collaborative Planning

At this point, you can start brainstorming dates together:

• "What restaurant have you been wanting to try?"

• "What movie do you want to see?"

• "I'd love for you to plan something - I'm excited to go along"

This takes pressure off you to always be the planner and makes dating feel more like a team effort.

Real Examples from My Relationship

Movie date: We saw "We Live in Time" (fair warning: incredibly sad - not recommended unless you're comfortable crying in front of your partner)

Concert: Maggie Rogers at Madison Square Garden - one of our favorite dates so far

Comedy show: Great for couples who enjoy laughing together

Chinese takeout and TV: Sometimes the simple dates are the most meaningful

The Dating Mindset Shift

From "Have To" to "Get To"

Instead of thinking: "I have to plan something for this weekend"

Try thinking: "I get to plan something fun for this weekend"

This reframe changes everything. Dating becomes something you're excited about rather than another item on your to-do list.

Managing Expectations

Don't put enormous pressure on yourself to create perfect, life-changing memories with every date. The goal is to:

• Get to know someone better

• See if you enjoy spending time together

• Be completely yourself

• Have fun and create natural connections

The Excitement Factor

How cool is it that we get to be nervous and excited about meeting new people? In your twenties, you're in a unique position to experience the thrill of potentially meeting someone who could become a significant part of your life.

Universal Dating Principles

Be Completely Yourself

This cannot be overstated: Never dull your personality or put on a front because you think that's what the other person wants.

Look for someone who:

• Brings out the best in you because you're fully yourself with them

• Shows you that they're being authentic too

• Makes you feel comfortable being genuine

Go with the Flow

The best dates happen when:

• You set hopeful, excited intentions going in

• You roll with unexpected changes (like restaurant closures)

• You focus on enjoying the person's company rather than executing perfect plans

Communication is Everything

Whether it's your first date or your fiftieth, clear communication makes everything easier:

• Be honest about your comfort level

• Share what you're looking for

• Ask questions about their preferences and interests

• Don't be afraid to have those awkward but necessary conversations

The Financial Reality

Dating costs money, and that's okay to acknowledge and plan for:

Budget-friendly options:

• Happy hour wine/drinks

• Coffee or ice cream dates

• Cooking at home

• Free events like museum days or outdoor concerts

When to invest more:

• When you're genuinely excited about the person

• For special occasions or milestone dates

• When you want to try something you'll both enjoy

Remember: Expensive doesn't equal better. Some of the best dates are simple and low-key.

Red Flags and Green Flags

Green Flags to Look For

• They handle unexpected situations well (like venue changes)

• Conversation flows naturally with comfortable silences

• They seem genuinely interested in getting to know you

• They're being authentic rather than performing

• You feel like yourself around them

Red Flags to Notice

• Everything feels like hard work

• They're constantly on their phone

• You feel like you need to be someone else to impress them

• They're rude to service staff

• The conversation feels forced or one-sided

For Different Relationship Goals

If You're Looking for Something Serious

• Be honest about your intentions early on

• Look for compatibility in values and life goals

• Pay attention to how they treat others

• Consider whether you can see a future together

If You're Dating Casually

• Be upfront about what you're looking for

• Don't lead anyone on who wants something more serious

• Keep things light and fun

• Respect boundaries and expectations

The Long Game Perspective

Dating is a never-ending cycle - whether it's with the same person or different people throughout your life. The skills you develop now will serve you forever:

• Planning thoughtful dates

• Reading social situations and vibes

• Communicating your feelings honestly

• Being authentically yourself

• Handling rejection and disappointment gracefully

Building Dating Confidence

Like any skill, dating gets easier with practice. Each experience teaches you:

• What you're looking for in a partner

• How to communicate more effectively

• What date activities you enjoy most

• How to handle nerves and anxiety

• What your own relationship needs are

Taking Action: Your Next Date

If you have a date coming up:

1. Choose a location where YOU feel confident and comfortable

2. Listen actively during conversation for clues about future date planning

3. Be genuinely yourself rather than trying to impress

4. Set excited, hopeful intentions rather than anxious expectations

5. Trust your gut about physical intimacy and relationship progression

If you're in a relationship:

1. Take turns planning dates to share the creative burden

2. Try new activities that you can experience together

3. Have those awkward but important conversations about where things are heading

4. Show your authentic self in comfortable environments

5. Remember that date night is something you GET to do together

The Bottom Line

Great dates aren't about perfect execution or expensive venues. They're about creating opportunities for genuine connection with someone you're excited to get to know better.

The best dates happen when you:

• Feel comfortable and confident in your setting

• Are completely authentic and encourage the same in your date

• Focus on enjoying each other's company rather than meeting expectations

• Handle unexpected situations with humor and flexibility

• Communicate openly about your feelings and intentions

Whether you're planning your first date in months or your fiftieth date with the same person, remember that dating is fundamentally about human connection. Keep it simple, be yourself, and enjoy the process of getting to know someone new or rediscovering someone you care about.

The anxiety and excitement you feel? That's not a bug in the system - it's proof that you're putting yourself out there and creating opportunities for meaningful connections. And that's pretty amazing.

Need more dating advice or want to share your own date experiences? Listen to new episodes of Guyset every Tuesday on your favorite podcast platform for more real talk about relationships and dating in your twenties. Sign up for the weekly newsletter at guyset.com, email josh@guyset.com with your questions, or connect with us @theguyset on social media.

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