5 Ways To Date Yourself On Valentine’s Day And Fall In Love All Over Again

Sharing is caring so please share this post!

Learn how to date yourself in fun ways that will help you discover and fall in love with who you really are.

Disclaimer: Posts may contain affiliate links. We earn commissions if you shop through the links on this page. As an Amazon Associate, we earn from qualifying purchases. For more info, read our disclosure policy.

Learn how to date yourself in fun ways that will help you discover and fall in love with who you really are.

This post is long overdue, maybe 15 years overdue.

It’s the post I wish I’d read when I was in my teens and all the way to my early twenties, when I was obsessing over the fact that no one has ever asked me out on a date – except maybe for one or two boys who may or may not have asked me after being prompted by their mothers.

Not exactly the ringing endorsement that a young girl is looking for and I’d be the first to admit that my fragile teen ego took a direct hit too many times to count.

Of course, back then, self-love wasn’t really a thing. And its importance hadn’t filtered through the old country’s very conservative society – the society I grew up in.

Anyway, fast forward 15 years and I now know the truth: that true love begins from self-love and that Valentine’s Day is a time when you can fully celebrate that.

in other words, this isn’t just a post to give you a list of things that will teach you how to enjoy Valentine’s Day when you’re single. 

I honestly really believe that all of us need to take ourselves out on a date even when we’ve been married for 25 years.

You need to celebrate, not just your love for your partner, but also for yourself.

It’s a good thing to do and so important that I’m so tempted to call it a requirement.

So, learn how to date yourself on Valentine’s Day and, more importantly, why you need to do it even when you’re not single!

What is the real story of Valentine’s Day?

So, if the quick answer is that Valentine’s Day is the day of mostly romantic love, what’s the the story behind it?

What is the real story of Valentine’s Day?

If we’re delving in history (and we are, just not very deeply), then the answer to the question becomes quite murky.

The common answer is that Valentine’s Day is actually a shortened version of what is really the Feast of St. Valentine or Saint Valentine’s Day.

Just like dear St. Nick, who reigns supreme on Christmas, Valentine’s Day is also a primarily Christian tradition.

Not surprisingly really, since Christianity is built on the premise that love is all-important.

Naturally, there would be an entire day dedicated to celebrating it.

“Okay, that seems simple enough,” you might say. “Where’s the murky bit?”

Well, in the first instance, we’re not even really sure which St. Valentinus we’re celebrating. There were two: Valentine of Rome and Valentine of Terni, both of whom were martyred for their faith.

In other words, the real story of Valentine’s Day had nothing to do with romantic love – at least, originally. It was actually to commemorate one or both of these saints.

Of course, the more common legend is that Saint Valentine was “a priest of Rome who was imprisoned for succouring persecuted Christians” and then performed a miracle by healing the blind daughter of his jailer before his execution.

It wasn’t actually until the 14th century that romantic love began to be associated with St. Valentine’s Day and people started giving their romantic partners flowers, chocolates and greeting cards (AKA valentines). Until it’s become the celebration we know today.

Side Note: There was actually a third Valentinus, martyred in Africa with a number of companions, but sadly nothing more is known about him. 

Why do we celebrate Valentine’s Day?

In many countries, Valentine’s Day is the day you give your partner a romantic gift to show how much you love them.

In other countries, the gifts are given to children or from children to their parents.

All in all, I think it’s safe to conclude that Valentine’s Day is the day we’ve collectively chosen as the day to honor love in our relationships.

I personally think that this is a great idea – honoring love in our relationships.

But guess what relationship suffers the most on this day?

Can you guess?

Yep, it’s people’s relationship with themselves.

Self-love is the one love that somehow gets left behind on the 14th of February.

What do you do on Valentine’s Day when you’re single?

I honestly, really abhor this question. 

It’s almost as bad as these other oft-googled questions: “How can I be happy on Valentine’s Day?” or “What can I do on Valentines Day by myself?” or even “What can I do for Valentine’s Day without a date?”

I loathe these types of questions because they imply that Valentine’s Day is only for those who are paired up, and that simply isn’t the case. 

Okay?

Repeat after me: Valentine’s Day celebrates the finding and giving of love. And self-love is the cornerstone of all love.

Make sure you really capture that.

Valentine’s Day is supposed to be about love and self-love is the cornerstone of all love.

In other words, being single on Valentine’s Day means you could actually focus on yourself and this, if you’ve not done it before, could be the best thing to ever happen to you. 

And no, I’m not just saying that because I was a bitter teenager with no date prospects who had to date herself.

It’s true that I didn’t have a date with someone else about 10 years ago.

But guess who I had a date with?

Myself.

And that’s the best thing to ever happen to me because I realized that I’m actually really great company.

That’s really why you need to date yourself first on Valentine’s Day (or any other day!): so you can get to know yourself. 

Discover what you really want.

Know for sure that you’re on the right path, that you’re doing the things that you’re doing because you want them to and not because that’s what other people expect you to do.

Find out what it is that makes your heart sing and makes you get up every morning with a smile on your face and hope in your heart.

Are you truly happy? Are you truly loved?

These are important questions that many of us gloss over or don’t even get to ask because of the many things we have to do.

The noises of the world and the competing desires of other people all clamor for our attention.

But when you’re by yourself, when you make it a point to take you out on a date, you’ve got the chance now to really delve deep into the inner workings of your mind.

And discover your heart.

When I was younger, I’d deliberately go out to a fancy restaurant on Valentine’s Day, dressed in my finery and enjoy an especially nice meal – the kind I don’t normally splurge on. Usually, I bring a book when I go out for meals and I’m by myself but on Valentine’s Day, I bring a journal and start reflecting, start making plans.

Sometimes, I’d go catch a movie with yours truly. I often invariably end up choosing a comedy romance, which is easy to do on Valentine’s Day because there are so many available everywhere.

There is plenty to do, once you get past the underlying message that society tries to serve you which is that to be happy, you need to be all loved up in a romantic relationship.

That’s not the case at all.

In fact, my best Valentine’s Day was in 2013. And I remember it well.

I was celebrating with myself somewhere in East Sussex with a glass of wine and a plate of gourmet chocolates. I had spent the day walking on the rocky shores of Brighton and enjoying the cool sea breeze as it whipped my hair, reminding me of quiet starry nights onboard the Mariner of the Seas, the very first Royal Caribbean ship I worked on.

That day, I tried to make out the horizon – that line that has always called out to me, promising new adventures – and I marveled at the many breathtaking turns my life had taken.

And I was happy, content in a way my restless spirit has never been.

In fact, as I grew older, I began to appreciate the time I spent with myself on Valentine’s Day and even now that I’m married and have a child, I still make sure to spend at least a few hours to myself on this day.

Taking yourself on a date on Valentine’s Day

What about you?

Have I made you think twice about going at it alone? And on this day of mostly romantic love no less? 

Maybe you’re already partnered up and you never considered to celebrate a part of Valentine’s Day with yourself. Why would you when you could spend it with your significant other?

Maybe you’re recently single and the thought that you’d be alone on Valentine’s Day is too emotionally wrenching to contemplate. And why should you have to go out and face the pity and censure of all those other loved up couples going on date nights when you can stay at home – away from prying eyes and pitying glances?

Maybe you’ve been single a while and you don’t actually care what happens because you’re not looking for a relationship. Like, who cares, right?

Maybe you’re asking, “Why should I date myself on Valentine’s Day?” Why bother when Valentine’s Day is just like any other day? Seriously, it’s just another mark on the calendar, isn’t it?

So, why take yourself out on a date on Valentine’s Day?

What’s a good reason?

Other than the fact that yours truly is encouraging you to do it?

What’s in it for her?

Well, it’s true that Valentine’s Day is just like any other day. But what does “any other day” look like for you?

How do you normally spend your days?

If your life is filled with love, joy, excitement and hope for the future, then you may be right and you might not need to do anything differently because you’re already living the life of your dreams. 

Why fix what isn’t broken?

However, if your days seem endless and your nights come as a relief because you now can stop thinking about what might have been or what your life could be, if you’re lost in an existential crisis of the soul and you’ve started asking questions along the lines of “Why am I here? What is my purpose in life? What am I doing all this for?” a la Eep in that fun family movie, The Croods…then, maybe then, it’s time to shake things up.

Do something new.

Brave the social restrictions on Valentine’s Day and go have a blast with yourself.

Take yourself on a date.

Love yourself.

Do something that’s just outside your comfort zone or maybe even something well beyond it, something personally terrifying that will change you forever.

It could be as big as going to a different country and making a new life for yourself there or as small as trying a different flavor when you order a cup of coffee from your local Starbucks.

Don’t you see?

The world is your oyster and you can do anything you truly wish.

Side Note: I want to put a practical caveat here: Make sure whatever you want to do is legal where you live. Remember that you can be, do and have everything you want – so long as you're not breaking the law and getting yourself in trouble. There are some things that are worth the world, but think hard if it involves crossing a legally drawn line.

Anyway, this is why you should date yourself on Valentine’s Day.

In fact, this is why everyone should date themselves on Valentine’s Day!

That’s my personal opinion.

Everyone should take themselves on a date on Valentine’s Day.

You. Me. That stranger crossing the street.

We could all do with a good dose of self-love. 

And discovering self love on Valentine’s Day, when the whole world seems to go all out in celebrating the finding and receiving of love, can be quite special.

How do I spend Valentine’s Day alone?

If you’re still reading, then I’ve hopefully managed to convince you that it’s very important to take the time to be alone on Valentine’ Day so you can go on a date with yourself.

But wait, what exactly are you supposed to do when you’re on a date with yourself?

Another excellent question!

There are obviously many options to choose from and the beauty of taking yourself out on a Valentine’s Day date is that you can make it all about you.

You get to do what you want to do. And you don’t have to ask (drag, beg?) someone else to do it. 

You can just go whenever you want wherever you want.

Of course, that doesn’t really help if you’ve never done this whole self-date thing before and you have absolutely no clue what to do (other than the few ideas I’ve touched upon in the previous sections, that is).

That’s why I’ll be sharing with you my favorite ways to spend the day that will show you exactly how to take yourself on a date on Valentine’s Day.

Enjoy!

Learn how to date yourself #1: Challenge Your Mind

Okay, so I’m a loner and on top of that, a firm believer in Jim Rohn’s statement, “The major key to your better future is YOU,” which is probably why meditation never leaves my list.

In fact, I’ve said from the very beginning that if change is what you seek, if you want to live a better, more blissful life, you need to start with your mind. And meditation can really help you with that.

There’s just no other better place to start, in my personal experience.

Everything is filtered through your mental faculty.

Imagine trying to create a rich, dynamic positive life from a mind that is exhausted and swimming in fear and negativity all day every day.

Can you imagine trying to attract your soulmate, the best romantic relationship you can possibly envision, when your mind is telling you that you’re not worth loving?

It’s just not possible.

Earl Shoaff once said, “We are creators. Nothing comes to us. Everything comes through us, from us. Everything in this world comes from here (inside us), not out here. So everything that you have in your life is exactly what you design.”

So, personally, I start the day (actually, any day but Valentine’s Day is particularly apt) with a meditation sequence geared towards cultivating self-love from Lisa Nichols.

If you need help trying to meditate because your mind won’t quit talking, I highly recommend Centerpointe’s Holosync Technology. It literally tunes me into the right frame of mind for meditation at the press of a button.

Or use Sensate!

Learn how to date yourself#2: Challenge Your Body

Before I had a child, I used to spend a huge bulk of my time working out, not because I’m gung-ho (although I can be when warranted) but because I loved the thrill, the exhilaration.

It just felt really good!

So, my Valentine’s Day always started with meditation, which was followed soon after by one routine from the Zumba Fitness Transformation System DVD Set. 

If I had enough time, I’d do it for 3 hours at a time. Sometimes twice that day.

That’s how much I loved it.

My goal wasn’t even to lose weight.

I just loved the feeling I got when I’m moving my body to the music.

And before I knew it, I was in the best shape I’ve ever been in.

Now, obviously, this isn’t a lose weight post (or blog) and I’m not saying you need to absolutely lose weight or get into your best shape (though you could, if you wanted to).

It’s important to accept who and what we are and the limits of what we can do.

It’s all well and good to want to lift 50kgs but if you’ve never done it before, you might want to temper your enthusiasm and start with 1.5kgs.

However, at the same time, we also need to heed the scientific research (there are many!) that shows us the benefits working out confers. This has nothing to do with shaming anyone for their weight and everything to do with making sure that your body and your mind (because they are inextricably linked), are performing at their absolute best.

I can tell you from personal experience that it’s difficult to work hard, perform well or get the results you want in any area of your life if you’re sick, if your body is weak or if you’re wrestling with mental health problems.

And you’re more likely to succumb to all three if you’re not exercising.

I know because that’s happened to me.

Of course, now I have a child and a business that’s taking off, which means I simply have no more time to do 3-hour exercise routines.

I’m also older, which means my body can only do so much.

For a time, I was beating myself up for this.

But eventually, after a great deal of inner work, I’ve finally managed to make peace with the fact that I’m going to have to approach fitness a lot slower than I would’ve liked.

Now, what I do is take advantage of the opportunities I have. I’ve invested in a walking desk (which has given me tremendous benefits), and highly recommend you do the same. Or you could try a bike desk, workout desk, ball chair desk, or another type of desk exercise equipment.

Learn how to date yourself #3: Explore Your World

On this Valentine’s Day, make the time to go and travel because “travel is the only thing you buy that can make you richer” (source unknown).

You don’t even have to go somewhere exotic and far away.

That said, if your goal is to discover more of who you are and more of what the world has to offer, there is nothing quite like the adventure of traveling to a different country. Not only will you meet new people and enjoy new experiences, you’ll also come face-to-face with parts of yourself you’ve never noticed before.

I highly recommend the whole solo traveling experience – Valentine’s Day or not.

But as I said, you don’t have to go to far-flung places. If you’ve never travelled before then the act of going on a trip could be a stretch but you don’t have to stretch so far that you have to leave for days on end.

Even a few hours of exploring something new and different could be enough.

You could just drive to the nearest town, which you’ve never visited in the 20 years you’ve lived in your home.

Visit that art gallery everybody’s been talking about.

Browse the items in that controversial shop down the street and see if you might actually like what they stock.

Book an AirBnB somewhere a few hours away where all the tourists go for the history or culture or whatever other reason and see for yourself what all the fuss is about.

Or book yourself somewhere so remote they don’t have WiFi or broadband and enjoy the experience of being totally unplugged from the stream of information that flows all around us via the internet.

Watch a play in one of those big theaters and really immerse yourself in the experience.

Create a feel good playlist and dance to it like the world is ending and the only thing that can save it is music and the way it makes your body sing.

Allow yourself to be touched by what you see, hear, smell, taste, experience.

Discover what makes you laugh – that deep, belly laugh that goes on and on because you’re so happy it spills out from the hidden depths of your heart and comes pouring out your mouth.

Find out what makes you cry – with happiness, with sadness, with hope. What tugs at your heartstrings so hard that your eyes form tears?

Explore the world around you and remain open to everything in it.

Because, in the end, traveling or exploring, isn’t done solely for its own sake. 

You travel to see the world, yes. You go out on an exploration to see what else is out there.

But, if you’re open enough to the experience, what you’ll find isn’t the world outside. 

You’ll realize that this brand new thing you’re looking at is a whole new universe that has always existed inside of you. But which you’ve never realized was there until the experience of exploration, of traveling, allowed you to uncover it.

So, this Valentine’s Day, make it a mission to explore what you’ve never explored before.

Set yourself free.

It could be the day that irrevocably changes your life for the better.

Learn how to date yourself #4: Explore Food

Hi, I’m Vanessa and I love to eat.

Now, I wouldn’t go so far as to say that eating gives me the high that exercising does. Though if the food is fresh, prepared well and tied to the cultural experience of exploring a brand new place, then it can be quite the exquisite experience.

This Valentine’s Day, consider trying that restaurant you keep seeing or reading about. The one that’s serving up dishes you’ve never tried before. The one that offers a culinary experience like no other.

For example, I’ve been keeping tabs on one intriguing dining experience that I first heard about a few years back. It’s called dark dining. Have you tried it? I’ve been meaning to do so but haven’t managed yet. It’s high up on my list though and perhaps, you might want to put it in yours. 

According to Wikipedia, “Dark dining takes place in a dark restaurant, where the customers do not see the food they are eating. The basic concept is that the removal of vision enhances the other senses and increases gastronomic pleasure. Since 1999 such restaurants have opened in many parts of the world.”

It’s definitely an out of the ordinary experience but it promises to be a really good one.

After all, when we take a bite of something truly delicious, our immediate reaction is too close the eyes.

Another thing I do is to try different cuisines. It’s how I discovered that I rather like Lebanese food (or maybe the slightly Westernized version of Lebanese food anyway).

If you want to go for food as it’s normally cooked by local for locals and you’re not in their country, you’ll have to do a bit of digging and find out where the locals like to congregate for food.

Top tip from my cruising days: The best way to tell if you're enjoying local cuisine is when you see no other tourist in the restaurant. If there are mostly locals there and there are a lot of them enjoying the food (and maybe giving you curious sidelong glances), you've found a place that caters not to the tourist-y palette.

I also live up to the hype of taking myself on a date.

And by that, I mean I get my fanciest clothes and really dress up. When I have money to spare, I’d even get my hair and make-up done (but mostly because I’m hopeless at both of them), go for a mani-pedi spa and book a five-course meal – something I don’t often do.

I’d even splurge on a nice, fizzy drink which is something I don’t often do.

Another top tip: If you're self-dating, limit any alcoholic beverage to 1 and watch your glass. You won't have anyone to make sure you get home safely. And in this, as in anything else, safety first, right?

Once at the restaurant, I just sit back and relax, glorying in the feeling of enjoying a good meal that I didn’t have to prepare myself  or have to clean up after. 

Now, if this is the first time you’re doing this, you might feel a bit weird. I mean, what do you do when you’re not eating? You have no one to talk to or even look at.

If you’re an introvert, that’s actually not a problem.

But if you love company or the social scene, this might be a painstaking experience – at least, at first.

That is, until you get to know yourself more.

And this is actually, one of my favorite settings for some of my deepest inner work.

I can’t explain it but somehow I discover more about myself when I’m sitting in a place where there are other people around me who aren’t talking to me and may not even be aware I exist.

It’s like my soul craves some sort of reminder that I’m connected to the world but rejects being fully immersed in it, if that makes sense.

And how exactly do I do my inner work here?

Simple: I take a journal or a blank piece of paper along with me and start brain dumping, setting goals and making plans.

Now, if you don’t want to go out but would love to treat yourself to amazing food, why not join a cooking masterclass by a famous chef? Learn from Alice Waters, Gordon Ramsey, Wolfgang Puck, Thomas Keller, Roy Choi, Madhur Jaffrey, Mashama Bailey, Gabriela Cámara, Dominique Crenn, Niki Nakayama, Massimo Bottura, or Yotam Ottolenghi – and enjoy fantastic food this Valentine’s Day.

Just. For. You.

Learn how to date yourself #5: Get In Touch With Yourself

This one should really be at the top of my list because I love it so much.

Even when I was younger and I could never manage to sustain it for an extended period of time, journaling has been such a helpful experience for me when I’m diving deep.

One good thing about it is that you can basically do this anywhere.

You can go to the library, the park, a quiet cafe with just yourself and your journal for company.

I often combine this with good food in a good restaurant (see above section).

You might even take a pair of headphones to block out the surrounding noise and really focus on what goes on inside you.

Heck, you don’t even have to go out, you can just stay at home and do your journaling after a long hot soak in a scented bath or a luxurious spa day meant to indulge the senses.

I personally love journaling, especially the part where I’m going out and staying in a cafe or a restaurant by myself, perhaps because it happens so rarely now that I have a child and far too many things to do. Such times are hard-won and are so precious to me.

Journal prompts for self love on Valentine’s Day

1. What do you love most about yourself? Create a top 10. Pause and feel grateful for all the good things that are within you.

2. What do you not love about yourself? Create a top 10. Pause and feel grateful for all that makes you you. Then decide if these things are things you wish to change. If yes, make a plan on how best to do that. Be realistic and kind. It takes time to change things about yourself that have been there for ages.

3. What turns your light on? How can you make sure that this becomes a part of your daily discipline?

4. What turns your light off? How can you make sure that you don’t do any of these things?

5. What needs do you have difficulty making time for? How can you make sure you always have time for them now, moving forward?

6. If you had any advice for your younger self, what would it be? If you had any reminders for your future self, what would it be? Write the love letter you’ve always wanted to receive.

7. What are your strengths?

8. What are your weaknesses?

9. How do you look after yourself every day?

10. What do you need to do more of every day?

11. What do you need to do less of?

12. What are you most proud of?

13. If you could do absolutely anything (and you have no constraints like money or time), what would you do?

14. How are you feeling right now?

15. Who or what inspires you the most? How can you make sure that they take a prominent place in you life so they can continue to inspire you?

16. Describe your most unforgettable experience? Why did this make such an impression on you?

17. What are you passionate about?

18. If you were queen of the world, what would you change first? What would you make sure to keep? Why?

19. What is the one thing that would really do it for you, the one thing that will make you smile with satisfaction and say, “I really am living the life of my dreams.”?

20. You deserve love because …

Final Thoughts on taking yourself on a date

And there you have it: The Ultimate Guide To Celebrating Valentine’s Day with a totally kick-ass person who deserves all the love in the world. For more ideas, check out our post, 100+ Unusual Self-Care Ideas To Turbocharge Your Life!

Take Yourself on a Date Now

Note: The information on this website is for general information only, and is not a substitute for medical, financial, or legal advice. You, or anyone you are concerned about, are encouraged to seek independent medical, legal, financial, taxation or other advice to check how the website information relates to your unique circumstances.

If you or the person you are concerned about appear at risk of self-harm or harm to others, please seek immediate professional assistance.

Sharing is caring so please share this post!