Next week is Valentine's Day how exciting! I'm not gonna lie, this one is definitely chaotic. I give advice for people in relationships even though I’m single and of course advice for single people as well as questions to ask yourself and think about around this time. There's also a new section called Advice Guy at the end where I answer 2-3 questions you guys send in each week! I used to do this once a month but didn't want to wait that long to give advice or recommendations so now you can find it at the end of every episode as well as once a month in a longer format.

The Ultimate Valentine's Day Guide for Guys: Single & Taken Edition

Originally shared on the Guyset podcast - a guy's guide to what should be talked about

My Valentine's Day Horror Story (And How to Avoid It)

Let me start with a confession: I once committed one of the worst first date sins possible. Last year, I accidentally scheduled a first date on Valentine's Day. Yes, you read that right - Valentine's Day.

I had planned the date a week prior, completely oblivious to what day it was. When I finally realized on Tuesday that my Thursday date was on February 14th, I literally said "fuck" out loud. There I was, about to meet someone for the first time on the most romantically charged day of the year.

Why You Should Never Go on a First Date on Valentine's Day

Here's what made it so awkward: instead of being surrounded by other nervous first-daters (you know, the guys squirming in their chairs waiting for their dates to arrive), I was surrounded by couples holding hands and making out. The whole atmosphere was charged with love and romance, which put massive pressure on what should have been a casual getting-to-know-you conversation.

I ended up buying a single rose on the way there, telling her I just realized it was Valentine's Day and felt bad. The date was fine - good conversation, no major spark - but she ultimately wasn't interested in a second date. Even though I wasn't deeply invested, getting that rejection text still sucked.

Bottom line: Don't set yourself up for failure by scheduling first dates on Valentine's Day.

If You're Single This Valentine's Day

Embrace It as Just Another Friday

This year, Valentine's Day falls on a Friday. Instead of wallowing or putting pressure on yourself to find a date, treat it like any other weekend night:

• Go out with your single friends

• Have a low-key night in

• Hit the movies

• Order takeout and binge-watch something

• Go to the gym

• Focus on your hobbies

Keep Putting Yourself Out There

Here's the thing about dating: it's like going to the gym. A year ago, I couldn't do a single pull-up. Last week, I did 10 in a row for the first time ever. It took consistent effort, twice a week, for an entire year.

Dating works the same way. I went on countless mediocre, okay, bad, and good first dates over two years before finding someone I really connected with. Each date was practice, getting me closer to where I wanted to be.

The Reality of Rejection

Those rejection texts always suck, whether you were super interested or just mildly curious about a second date. Your heart drops every time. But rejection is part of the process - it happens with jobs, raises, and everything else we want in life.

The worst thing that can happen is someone saying no. And honestly? That's not that bad in the grand scheme of things.

Remember You're Not Alone

Look around next time you're on a date - you'll see other guys nervously waiting, just like you. We're all out here trying. Some of my friends are in 8-year relationships, others are single, some just got out of relationships, others are on their first dates in years.

Everyone's in a different phase, and comparing yourself to others means nothing. You don't really know how anyone's relationship looks from the inside.

If You're In a Relationship This Valentine's Day

Make Your Plans NOW

If you're planning to go out to dinner and haven't made a reservation yet, you're in trouble. I tried booking something last week and restaurants were charging $250 per person for private rooms in cocktail bars. The cancellation fees alone were $100.

I finally found a reservation at a place I liked, but it was a battle. If you haven't booked yet, you might want to consider Plan B.

The Essential Valentine's Day Checklist

Before anything else, get these basics right:

1. Flowers - Buy them the day before, not day-of when they're impossible to find

2. Chocolates - CVS has everything you need in their Valentine's section

3. A small gift - Think teddy bear, keychain, or something cute that reminds you of her

Honestly, paying for dinner + flowers + chocolates is more than enough, especially since Christmas was just two months ago.

Gift Ideas That Actually Work

I consulted actual women for these suggestions (shocking, I know):

Cozy & Comfort:

• Warmies (stuffed animals you can microwave to warm up)

• Silk sleep eye mask or Nod Pod

• Slippers and cozy blankets

• Pajama sets

Cute & Personal:

• Heart waffle maker

• Disposable camera for memories

• Custom jewelry based on her birth sign

• Silk hair ties or claw clips

Experiences:

• Concert tickets for an artist you both like

• Nice restaurant you've both wanted to try

• Spa day or couples massage

The Plan That Actually Matters

Here's the secret: Valentine's Day is about quality time with someone you care about. Don't stress about finding the perfect place or spending tons of money.

My recommended formula:

1. Decide on your activity (dinner out, cooking at home, etc.)

2. Make a signature cocktail to share beforehand

3. Have your flowers, chocolates, and small gift ready

4. Focus on enjoying each other's company

If you're cooking at home, try making heart-shaped pizza together. If you're going out, arrive early and have that signature drink first.

Keep It Pressure-Free

Remember, this is a Hallmark holiday at the end of the day. If your partner cares more about how much you spend than the thought you put in, that's probably not the right person for you.

The goal is to show you care and want to spend quality time together. Everything else is just bonus points.

Valentine's Day Alternatives

For the Homebodies

• Cook a special dinner together

• Create a cocktail tasting menu

• Have a movie marathon with her favorite films

• Build a blanket fort (yes, really)

For the Adventurous

• Take a mini road trip somewhere new

• Try a cooking class

• Go to a comedy show

• Plan a picnic if weather permits

For the Practical

• Plan a weekend getaway for later in the year

• Start a new hobby together

• Take dancing lessons

• Visit a museum or art gallery

The Real Valentine's Day Message

Whether you're single or taken, don't put too much pressure on this day. If you're single, know that your time is coming - keep putting yourself out there and taking those dating "reps." If you're in a relationship, focus on creating a moment that's about the two of you, not about impressing Instagram.

Valentine's Day should be about connection, whether that's with your partner or with yourself and your friends. Make it meaningful in whatever way feels right for you.

Josh shares more dating advice, relationship tips, and lifestyle guidance on the Guyset podcast. New episodes drop every Tuesday with honest conversations about navigating your twenties.

Need more dating advice? Check out previous episodes including "26 Minutes of First Date Advice" and "My Biggest Dating Mistakes" for more insights on modern dating.

Valentine’s talk starts at 5:12

Advice Guy starts at 21:23

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See you next Tuesday!