The Do’s and Don’ts of a Successful First Date on Valentine’s Day

Ideas for the perfect first date for Valentines Day

If you’ve successfully asked a girl out for a first date on Valentine’s Day, our first thought is, “What the hell were you thinking?”

Then, after laughing out loud for a minute or two, our second thought is, “Yeah, you got this!” and we’re here to help. So what if you asked her out on the most romantic day of the year that’s already tension-filled?

No biggie, but you will likely need a few tips to guarantee you make it through the date with your pride intact. Luckily, we’re here to assist with our list of Do’s and Don’ts that will give you the upper hand to make your date a successful one.

Benefits of a First Date on Valentine’s Day

Most people may avoid a first date on Valentine’s Day because it may seem like too much pressure. Should you get a gift? Shouldn’t you get a gift? Where to take your date? How much to spend? Oh, hell! There are so many things to consider. Screw that! You’ll put it off until the 15th.

Before you panic and reschedule, check out some of the benefits of going on a first date on the most romantic day of the year.

1. It Could Make a Romantic Story One Day

Think about if you actually form a relationship on Valentine’s Day. You’ll have a great story to tell all your family and friends, not to mention your (ahem) children and grandchildren. You can now celebrate the 14th as Valentine’s Day and the day of your very first date.

2. It Indicates You’re Both Relaxed

You asked, and she said, “yep,” so now it’s a go. Going out on Valentine’s Day shows that you don’t feel pressured by a day typically reserved for couples in love. Guys are usually impressed with girls willing to go out on that day without making a big deal or attempting to reschedule because it’s the lover’s national holiday.

For her, she may be impressed by the fact that you don’t go out of your way to avoid the day because “that’s what guys are supposed to do.” It’s another day, no more, no less, and that’s how you both view it.

man and woman on relaxed Valentines date

3. You Can Showcase Your Sense of Humor

Not a big fan of Valentine’s Day? Imagine hooking up with another hater. You can spend your date mocking the day. Screw all the rom-coms. Instead, download all your favorite anti-Valentine’s Day movies and binge-watch for a couple of hours. Not many people are aware, but some areas offer anti-Valentine’s Day activities, like haunted hay rides and karaoke with anti-love songs. Even if you are a fan of the day, you can still have fun partaking in the activities.

Don’t: Make Yourself Look Desperate

If you’ve ever asked out a girl you don’t really know on V-Day, she probably had one of two reactions:

1. She thought it was a kind and sweet gesture.

2. She thought it was bizarre and somewhat desperate. However, she decided to give you a chance anyway on the slim possibility you weren’t a serial killer but instead were a nice guy who was just trying to be sweet.

As we’ve previously mentioned, Valentine’s Day is typically for couples who have spent some time together. So, it’s imperative that you make sure she understands that asking her out on this specific day is a cool, laid-back gesture to get to know her.

However, you definitely don’t want her to think that your master plan is to ply her with drinks so you can whisk her off to Vegas for a cheap drive-thru wedding. So, when you ask, make sure you’re confident but not cocky. Your attitude should range somewhere between, You are the love of my life, and I want to be with you always and If you can make it, then great. If not, meh. Find that perfect in-between tone, and you will have secured a Valentine’s Day first date.

Do: Show Your Spontaneous Side

Valentine’s Day is typically reserved for couples and not for two people who have just met. This is why you must show her that going out on a first date for Valentine’s Day isn’t something you make a habit of doing every year. Ghee, how un-special would that be?

Make her understand that their date isn’t a recurring thing. Instead, you decided to do it at the last minute because you’re a spur-of-the-moment person.

How to Be Spontaneous

Does it seem bizarre to ask how to be spontaneous? Nonetheless, here we are. Surprisingly, there is a guideline to learning to be more random rather than plotting everything out.  Here are some methods to help you be more spontaneous.

Think less and live more. Like many others who desire to live a “typical life,” you wind up acting out the exact same day as the one before (For reference, see the movie Groundhog Day). Eventually, you question your existence on this earth and whether or not you’re living your best life. That said, having a little healthy spontaneity in life is essential to keep things exciting.

  • Say whatever you want: Have you ever been in situations and wished you hadn’t kept your opinion to yourself? To help boost your spontaneity factor, start speaking up. If someone makes a disparaging comment to or about you, tell them you don’t appreciate it. Likewise, if you want to ask someone out, but aren’t bold enough to do it, take a chance. What’s the worst that can happen?
  • Trust your feelings: It’s OK to be a rational, logical-thinking person, so don’t consider it a character flaw because it isn’t. However, there comes a time when being too analytical can hinder your life. When you regularly say no to things and ignore doing things despite your initial inclination of excitement, you may miss out. Instead, listen to your gut and trust that it’s guiding you in the right direction.
  • Do something different: When we have little free time from work, family, and financial obligations, we often hop on social media and spend hours scrolling. This becomes a habit until some new study comes out that indicates you’re spending way too much time online watching cat videos. This type of activity will not help you be more spontaneous. Break out of the norm and do something new. Join the gym or sign up for a cooking class. Make it something you’ve never thought about doing, and go for it

Don’t: Go to a Restaurant

Answer: Any restaurant

Question: Where is the last place you want to take your first Valentine’s date because the overcrowding on that day will probably guarantee you horrific service, which is not the best way to impress your date.

Trust us when we say that every single restaurant on Valentine’s Day will be packed from ceiling to floor, with couples making googly eyes at each other all night long. There are two issues with that.

  • As previously stated, the restaurant will be packed, which means sub-par service.
  • Because every couple will be swooning over one another around you, it may be uncomfortable for a first date.

So, unless you decide to take her to In-N-Out Burger, where you won’t need to deal with swooning couples but will have to deal with drunken partyers or screaming kids, you may want to steer clear of restaurants.

No Restaurants? No Problem

So, you’re going to take our advice and not take your date to an overcrowded restaurant. Unfortunately, you don’t want to take the food option off the table (no pun intended.) There are many other options to feed your date instead of going to a restaurant.

  • Take-Out and a Movie: Who says you can’t order takeout? If you both feel comfortable enough, order some Chinese food and chill at your place while checking out classic anti-Valentine’s Day movies (Friday the 13th, Drag Me to Hell, Nightmare on Elm Street)
  • Create an at-home picnic: This is almost the same idea as take-out, but instead of focusing on the movies, your attention is on the picnic and the conversation.
  • Movies: If you don’t want to check out a movie at home, why not head out to the movies? Most movie theaters now have a dinner option, so you can munch while you watch.
  • Picnic in the park: This is for guys that are really looking to impress their date. You can order the food or really impress her by packing the food yourself. It doesn’t have to be a 4-course meal. Pack some wine, grapes, and cheese to create a laid date. Tip: If it’s cold outside, be sure to bring a blanket so you both can snuggle together.
  • Casual lunch: Restaurants will be packed with romantic couples only in the evening. So, if you’re both available, take her to casual lunch. A brunch is also an option and allows you to enjoy mimosas. Yummy!
  • Make her dinner: Don’t miss out on an opportunity to impress her. If your cooking skills are out of this world, prepare your specialty dish. However, if they’re lacking, no worries. Do your best. Unless it’s god-awful and the remainder of the evening is spent in the ER, she’ll appreciate the effort.

Do: Take Your Date Someplace Casual

Let’s not make this into a whole grandiose event. Instead, keep it casual, so local bars are a great choice on Valentine’s Day. Think about it; the only people there on that day are the ones that couldn’t get a date, so when you walk in with your hottie, that’ll be a huge confidence booster. Boom!

Aside from raising your self-esteem, what’s better than sipping on a pint while sitting across from a beautiful woman while getting to know them better? Nothing, that’s what.

Don’t: Get Her a Card

No cards, please! They’re solely reserved for couples, family, friends, and sometimes even coworkers. Buying a card for someone you’re on a first date with is kind of weird. Besides, is there even a card for that?

Thank you for going out with me on our first date on Valentine’s Day because I don’t have a partner, and apparently, neither do you. I guess we can be losers together.

Hey, you never know. There have been worse cards out there.

Do: Get Her a Gift

So what you don’t really know each other that well? That doesn’t mean you should completely ignore that it’s Valentine’s Day.

That also means don’t go overboard with the gifts. Something like a colossal bouquet of roses doesn’t look good conspicuously positioned on a bar. Jewelry is also a big NO! However, a box of chocolates or something similarly cliche will always be a winner.

Great Valentine’s Day Gifts for Friends

You may not have a Valentine this year, but you have friends. Or, this is your first date with someone, and it falls on the most romantic day of the year. If this is you, check out these great non-romantic gift ideas.

  • For an artist: If your friend is into art, give them a classic art set that includes paints, aisles, pencils, and sketch pads. If they’re into pottery, try a pottery kit. You’ve just given them a gift that keeps on giving because now, you’ll get a new vase every birthday. Thank us later!
  • For ones into health and wellness: At food prices lately, someone into health would love a basket full of grocery items. Healthy prepackaged meals will help them attain their goals faster and easier. This way, they’ll stop trying to drag you to the gym to help them lose weight.
  • Sober friends: A nice bottle of sparkling cider is always a good gift. Consider a non-alcoholic cocktail kit that includes global cocktail mixers
  • For a baker: the latest baking gadgets and utensils are always a good choice. A popular seller is a cast iron pie dish. Your friend no longer has an excuse for not baking you a delicious apple pie.
  • A heated blanket: Since it’s February and cold in many regions, they’ll appreciate a cozy, warm, heated blanket, especially for that friend who’s always whining about how cold it is.

Don’t: Go Overboard

We spoke about gifts and what’s a good idea and what isn’t. Let’s now discuss going overboard overall on the date. Understandably, you may catch some of the feels on Valentine’s Day. The day is designed to throw slap you in the face with love. But if you have too many drinks and become swept away in the V-Day spirit, you may confess your undying love to her. Instead, dial it down a notch or two, enjoy the moment, and have some fun.

Do: Take Advantage of the Day

You may not specifically be celebrating the day, but let’s assume the date went off without a hitch. You got along, she laughed at all your stupid jokes, and she even flirted once or twice. The best part is, you didn’t vomit from nervousness or mistakenly pass gas. Score!

Remember, it is the most romantic day of the year, so if it all went all, why not go in for a kiss? WAIT! Before you do, be sure to read the signs to figure out if the great date was all in your head, and if you go for the kiss, will she reject you faster than a blink of an eye? To avoid being pepper sprayed, read the signs.

Signs That Say She’s Attracted to You

You’ve been interested in her for a while, but you can’t determine whether she’s interested in you. You’ve put out all the signals and still come up with nothing. Here are some signals that, yep, she’s attracted, so you better act before someone else scoops her up.

  • giving you short, quick glances
  • smiling at you
  • licking her lips
  • making constant eye contact
  • darting her eyes away when you glance at her
  • exposing her neck
  • turning her seat in your direction
  • moving closer to you
  • tilting her head toward you
  • laughs when you talk (at your jokes)
  • squeezing an object in her hands
  • runs her fingers through her hair
  • fixing or twisting her hair
  • brushing her fingertips over your arm or shoulder

Out of these signs, the most common ones are direct eye contact, smiling, and repeated glances.

Warning! Warning! Warning!

Yes, these are signs that she’s interested. Still, a socially inept noob will look at a list such as this, and every time he witnesses any of these signals, he’ll move in faster than a sidewinder in the desert, thinking she’s attracted to him sexually. Unfortunately, some men have difficulty figuring out these social cues, particularly one sexual in nature.

So, if you believe she is attracted to you, and you approach her, please ‘read the room.” If you notice she’s moving away from you or acting like she’s not interested, you misinterpreted the situation, so back off. It happens, but don’t make an awkward situation worse. Take the hint and move on because she’s not the one.

Likewise, if a female coworker touches your arm, don’t automatically assume she wants to ride off into the sunset with you and live happily ever after. Some people are super friendly and a little touchy-touchy. That may be just what they do to everyone. But if she isn’t that way with everyone but is with you, she may be attracted, and it couldn’t hurt to pursue that further.

Sure, Valentine’s Day is a time when couples celebrate their love. But not everyone is part of a couple. Besides, are you supposed to hibernate that day? No way! If you want to go out with her, then don’t let anything (or any day) deter you. Have a good time; if it works out, you’ll be paired up for next year’s Valentine’s Day. If not, you have a year to search for a new possible Valentine. Happy Valentine’s Day!

Leroy Vandalay
Leroy Vandalay

Leroy Vandalay is a dating app veteran with over a decade of experience using these services for his own personal life. He ultimately looks forward to sharing this acquired knowledge with you, the readers.