This episode is for every guy. I tell you about my mistake of going on a first date on Valentine’s Day last year, my advice for all the single guys on Valentine’s Day, and recommendations for guys in relationships. There’s something for everyone in here so happy valentine's day!

The Complete Valentine's Day Guide for Guys: What to Do Whether You're Single or Taken

Real advice for navigating February 14th, no matter your relationship status

Valentine's Day is coming up fast, and you're probably feeling one of three ways: excited, dreading it, or completely forgot it was happening. Regardless of which camp you're in, this guide has you covered with practical advice for both single guys and those in relationships.

Let's be real – Valentine's Day can be stressful no matter your situation. But it doesn't have to be.

The Biggest Valentine's Day Mistake You Can Make

Never Go on a First Date on Valentine's Day

Before we dive into what to do, let's start with what NOT to do. The worst Valentine's Day mistake? Going on a first date on February 14th.

Here's why this is setting yourself up for failure:

The atmosphere is all wrong. Instead of seeing other nervous first-date guys around you (which is oddly comforting), you're surrounded by couples holding hands and being romantic. This adds unnecessary pressure to what should be a casual get-to-know-you situation.

The expectations are skewed. First dates should be about seeing if you click and want a second date. Valentine's Day adds this heavy romantic undertone that doesn't belong in a "let's see if we like each other" scenario.

You'll feel more anxious. The combination of first-date nerves plus Valentine's Day pressure is a recipe for overthinking and stress.

The bottom line: if you've accidentally scheduled a first date for Valentine's Day, consider rescheduling. Your future self will thank you.

If You're Single: How to Handle Valentine's Day

Reframe the Day

Valentine's Day falling on a Friday this year actually works in your favor. Treat it like any other Friday night. Here's what to do instead of wallowing:

Hang out with friends. Get dinner with your crew, go to the movies, or just chill at home. Your other single friends are probably looking for something to do too.

Take the night off from dating apps. Give yourself permission to not think about dating for one night. You can get back to swiping on Saturday.

Remember it's just a Hallmark holiday. Seriously, it's a made-up commercial holiday. Don't let it define your worth or relationship status.

The Reality Check You Need

If you're feeling down about being single on Valentine's Day, remember this: you're not alone, and everyone's timeline is different.

Your friends are in all different stages. Some are in long-term relationships, some just started dating someone, some are single, some just got out of relationships. There's no "right" place to be at any age.

Rejection is part of the process. That heart-dropping feeling when someone texts that they're "not feeling it"? It sucks for everyone, and it's completely normal. It doesn't reflect your worth as a person.

Success takes time and practice. Think of dating like going to the gym. You don't expect to bench press 200 pounds on your first try. Dating skills, confidence, and finding the right person all take practice and patience.

Keep Putting Yourself Out There

The best thing you can do if you want to be in a relationship is to keep trying:

• Message people on dating apps even when you don't feel like it

• Shoot your shot at bars even if it feels awkward

• Go on dates even when you're not sure about the person

• Practice conversation skills because they improve over time

The worst that happens? You get rejected. And while that sucks, it's also how you eventually find someone who's genuinely excited about you.

If You're in a Relationship: Valentine's Day Planning

Make Your Reservations NOW (Or Don't)

If you want to go out to dinner: You're already late to the game, but don't panic. Reservations are tough to get and restaurants often charge premium prices or require tickets that cost $100+ per person. Some places even have hefty cancellation fees.

The better option: Make dinner at home. It's more intimate, way less expensive, and you can actually have a conversation without competing with every other couple in the city.

Fun at-home idea: Make heart-shaped pizza together. Buy the ingredients ahead of time and make it an activity you both enjoy.

The Essential Valentine's Day Checklist

These are the non-negotiables that will earn you serious points:

1. Flowers

• Buy them the day before, not day-of (they'll be picked over or unavailable)

• Order them in advance if you want something nice

• One rose is fine if you're on a budget

2. Chocolates

• CVS has a whole Valentine's section – make it easy on yourself

• Everyone likes chocolate, so you can't go wrong

3. Something small and thoughtful

• A little teddy bear

• A cute keychain that reminds you of her

• Something that shows you pay attention to what she likes

4. Pay for dinner and drinks

• Whether you're going out or staying in, cover the costs

• This plus flowers and chocolates is honestly enough, especially since Christmas was only two months ago

Gift Ideas That Actually Work

If you want to go beyond the basics, here are some ideas that girls actually appreciate:

Practical but cute:

• Warmies (stuffed animals you can heat in the microwave)

• Silk sleep eye mask or "Nod Pod"

• Heart waffle maker

• Silk hair ties or claw clips

• Cozy slippers or soft blankets

Skincare and beauty:

• Rhode lip products

• Summer Fridays skincare

• Silk pillowcase

Experiences:

• Concert tickets for an artist you both like

• Disposable cameras to create memories together

Personal touches:

• Nice candles (Homesick is a good brand)

• Love Pop cards with pop-up art inside

• Travel jewelry case if she travels a lot

Make It About Quality Time

Remember, Valentine's Day should be about spending quality time with someone you care about. Don't stress about having the perfect plan or spending tons of money.

Create a signature cocktail for the evening – something fruity she'll enjoy, or make it a mocktail if you don't drink.

Focus on connection, not perfection. The goal is to have fun together, not to recreate some Instagram-worthy romantic fantasy.

Take the pressure off. If she cares more about expensive gestures than thoughtful ones, that might be a red flag anyway.

The Mindset Shift That Changes Everything

For Single Guys

Stop thinking "everyone else has it figured out" because they don't. Your coupled friends have relationship problems you don't see. Your single friends are dealing with the same dating struggles you are.

Your time will come if you keep putting yourself out there. Every "no" gets you closer to a "yes." Every awkward date teaches you something about what you want and how to be better at dating.

For Guys in Relationships

Don't overthink it. The fact that you're reading this and trying to plan something thoughtful already makes you a good boyfriend. She'll appreciate the effort more than the expense.

It's about showing you care, not about having the most elaborate evening ever planned.

Valentine's Day Survival Tips

If Dinner Reservations Are Impossible

• Go early or late – try for 5:30 PM or 9:30 PM slots

• Try walk-ins at less obvious places

• Make brunch plans for the weekend instead

• Cook together – it's often more fun anyway

If You're Feeling Overwhelmed

Remember that this is literally a made-up holiday designed to sell cards and flowers. The pressure you're feeling isn't real – it's marketing.

If Money's Tight

The most important things (flowers, chocolate, quality time) don't have to be expensive. A thoughtful note explaining why you appreciate her, a homemade dinner, and genuine attention matter more than expensive gifts.

The Bottom Line

Whether you're single or taken, Valentine's Day doesn't have to be a source of stress.

If you're single: Use it as motivation to keep improving yourself and putting yourself out there, but don't let it define your worth.

If you're in a relationship: Focus on showing appreciation for your person through thoughtful gestures, not grand expensive displays.

At the end of the day, it's just another Friday. Make it fun, keep your expectations realistic, and remember that your relationship status on one arbitrary day doesn't determine your happiness or future.

Need more dating and relationship advice?

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See you guys next Tuesday.