Should You Plan a Valentine’s Day First Date?

Danielle Hayes

Feb 05 2019

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For many of us, the idea of a Valentine’s Day first date is something to approach with caution. But, why should we stay away from the most romantic day of the year when looking for love? Being single on Valentine’s Day isn’t always a lot of fun, so why not change that this year and try something new?

Choosing to have your first date on Valentine’s Day can be a bold move to take. The day is all about big, romantic gestures, and that can really put some people off. So, we’re here to settle the score once and for all. Is it awkward or romantic? A good idea or a bad idea? Should you plan a Valentine’s Day first date?

First Date On Valentine’s Day: Pros

Let’s start with the good stuff. You won’t be the first one to do this, and I’m sure you won’t be the last. So, let’s look at why it can be a great idea for your first date.


It’s already romantic

Half of the work is already done for you! The day is already filled to bursting point with romance, so you won’t have to try as hard to make it special. Almost everywhere you go, there will be decorations up, candles lit, and romantic music playing. The atmosphere will be set, and all you have to do is sit back and enjoy the ride.

Neither of you will have plans

It’s fairly safe to assume that two single people on a dating website will not have plans for Valentine’s Day. You can feel fairly confident when asking for that Valentine’s Day first date that them being busy won’t be an excuse not to go. It also gives you both something to do that doesn’t involve a night in alone watching romantic movies and eating ice cream.

It brings out your creative side

Most people who are out on Valentine’s Day will be celebrating the love of their long-term relationship. That means that restaurants are running special set menu’s that night, bars are selling tickets to their Valentine’s Day events, and a lot of the usual date options will have been taken over by loving couples.

But, this isn’t a bad thing. All it means is that you have to get a little bit creative with your first date plans. You’ll need to come up with some low-key date ideas that are a little out of the ordinary to avoid the Valentine’s Day crowd.

First Date On Valentine’s Day: Cons

If having your first date on Valentine’s Day is such a great idea, then doesn’t everyone do it? Well, there are still a few issues that can put people off, even though they really shouldn’t.


There’s too much pressure

Even when you’re already in a relationship, the pressure to do Valentine’s Day “right” is huge. We build up expectations around this holiday months in advance and expect the night to be the most romantic of our lives.

But, if you’re going on a first date, then the pressure starts to fall away. There won’t be any grand gestures or expensive gifts. Nobody is expecting to find an engagement ring hidden in their dessert. And you’re going into it knowing that it may well be a terrible match and you’ll never see each other again. Leave the pressure for those already in a relationship, and enjoy the night for what it is. And, if it does turn out to be awful, has some great advice for moving on as well as a bunch of new singles you can try again with!

You’ll be surrounded by people in love

Personally, I think that sounds like an amazing situation to be in. But, when you’re on your first date and everyone around you is holding hands, staring longingly into each other’s eyes, and kissing – so much kissing – it can be a little awkward.

But remember, it will only be awkward if you let it. Enjoy the happiness around you. Giggle together as you watch someone serenade their partner on the karaoke mic, or cheer with enthusiasm when the couple next to you gets engaged. You can still enjoy the romanticism of the holiday without taking part in it yourself.

What To Do On Your Valentine’s Day First Date

So you see, a first date on Valentine’s Day can be an amazing idea and no scarier or more awkward than any other first date! If you do decide to take the leap and ask someone out, here are a few tips to help things go smoothly.


Keep it low-key

Having your first date on Valentine’s Day is a great way to show how relaxed you can be while dating. If you’re able to have a low-key date on the most romantically charged day of the year, then you’re really going to be able to impress your partner.

Take the pressure off

This isn’t your anniversary, it’s a first date. The fact that it’s on February 14th makes no difference. It’s just another day of the year! I promise, your date won’t be expecting big gestures or big spending.

Of course, this doesn’t mean you shouldn’t try and make the date special, it is still your first date after all. You could be looking back on this for years to come. Top dating site eHarmony has a great list of first date questions you can ask to get to know your date quickly and naturally to get things off to a great start.

Be creative!

With places all getting booked up for Valentine’s Day well in advance, you’ll have to be creative with your first date ideas. Forgo the usual and be unexpected for your Valentine’s Day first date.

Low-key date ideas

  • Wander around the local zoo and see how many of the animals are celebrating Valentine’s Day too
  • Embrace your competitive side with a round of mini-golf or a trip to a video game arcade
  • Explore your local area with a geocaching scavenger hunt
  • Put the relationship to the test early on by taking part in an escape room together
  • Find out all the coolest street art in your city and take pictures of each other in front of it
  • Visit a bounce park together and release your inner child on the trampolines



The Verdict

First dates can be scary, awkward, and stress-inducing no matter what day of the year you have them. So, why shy away from Valentine’s Day just because it’s romantic? If you’ve met someone online who you really want to date, then send them a message and ask them out. What have you got to lose? It could be the start of an incredible story.

So make sure to sign up to one of the top online dating sites before February 14th to find your very own Valentine’s Day first date.

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