The “Anti-Valentine’s Day” Guide

Ease your Valentine’s Day Stress

Even if you don’t identify as someone who generally cares much about Valentine’s Day, many singles find that as this hallmark holiday approaches it begins to get to them. 

And that’s perfectly natural.

If you’re heartbroken and/or single this Valentine’s Day and could use a few ideas to either get you through this hallmark holiday, or even enjoy it and make it meaningful for yourself, this guide was created just for you.

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As silly as it might seem to some people, there is such a thing as “Valentine’s Day stress” and it’s associated with increased anxiety, depression, and insomnia. Although I’d never heard of this until a few years ago, I wasn’t surprised to hear it existed.

Valentine’s Day is loaded with romantic expectations that can distort our logical thinking and emotional well-being. Simply being aware that Valentine’s Day can have this effect can help you not take the weight of your emotions so personally.

I also want to remind you that being alone on Valentine’s Day (even if you are heartbroken) is far better than being with the wrong person or in an unhealthy relationship. Take some comfort knowing that you’re way ahead of this group!

Over the years of being single and/or heartbroken, I have tried many of the suggestions here myself.

One memorable year in 2012 a girlfriend and I had a great night drinking cheap beer at a heartbreak karaoke event, and then another year I picked up a nice dinner and binge-watched the show “Being Erika” with a glass (ok, a couple glasses) of one of my favourite wines.

The most important thing is to choose to do something that genuinely feels good. Forcing yourself to do something, such as going out when you want to stay in, may only make you feel worse - that was definitely my experience on a couple Valentine’s Days.


Here are some of my top suggestions, followed by a great list of recommendations from other singles and former-singles. Have a read and come up with a plan that feels just right for you!

Spend Quality Time With Your Single Friends

Spending quality time with your other single friends is one of the most obvious choices for how to spend Valentine’s Day. Whether you decide to make it a night out (for drinks, live music, or bowling) or plan on a night in with some good take-out and wine and perhaps a board game, it’s hard to go wrong with this option. 

Most cities host events specifically for people who don’t have plans, and the hidden benefit of this option is that the majority of the people out that night will be single! It will also serve to remind you that you are not alone and that there are a lot of other people who don’t have Valentine’s Day plans with their significant other. Perspective is everything.

Have A Date Night With Yourself

I’m often surprised at how many single people are not in the habit of having regular “date nights” with themselves. It’s as though they’re waiting to be in a relationship to enjoy certain “couple pleasures” such as trying out a great restaurant or recipe, seeing a particular movie, opening up that special bottle of wine, etc.

The truth is you don't have to wait for someone else to give yourself the love you want.

In addition to it feeling great, being good to yourself can also serve to increase your sense of self-worth because you are subconsciously communicating to yourself that you are worthy of love.

If doing nice things just for yourself seems unnatural, then this is a really great practice for you to develop. It will also help you in your dating life because people who take great care of themselves are naturally better in relationships and more attractive. It's win-win!

Design Your “Dating Plan”

If a part of your sadness come from the fact that you really do want to be in a loving relationship, then I encourage you to embrace that desire! Instead of feeling down about your status, get excited about the process of finding the love of your life.

I often compare looking for a relationship to looking for your dream job - you wouldn’t just expect it to just magically just happen someday! And yet, this is the approach so many people take when looking for a relationship. Instead you would be working to get clear on exactly what you’re looking for, and then actively working on your resume, actively networking, and skilling up!

The same principles apply to going after what you want in your love life.

I help many of my clients create a “dating plan” (much like a business plan) which includes gaining clarity on your core values, dating and relationship objectives, and coming up with a concrete plan that includes both online and offline dating strategies.

Creating a personalized dating plan is essential if you’re serious about finding a fulfilling relationship. 

You can start by picking up a great book on relationships or dating book, journal about what really matters to you in a relationship. We naturally invest in the things that matter most to us, so start investing your resources (time, energy and finances) in your love life!

A Couple Other Suggestions…

Here are a couple other resources to help to make the most out of your day:

  • Music Therapy - If you love music like I do, check out my curated playlists on Spotify! I highly recommend, Scorned if you’re feeling fiery, or Love is, if you want to tune into the kind of love you want to invite into your life. Just don’t listen to “Shattered, too sad.

  • Treat Yourself - Check out my gift guide for ideas on thoughtful gifts you can by for yourself.

  • Museum of Broken Relationships - If you have never heard of this museum, check out their website and their Instagram. It has great stories to help you feel less alone.


I have reached out to my online community for a few years now asking for suggestions for people who are heartbroken and/or singles on Valentine’s Day and here are some of my favourites (including wearing your favourite underwear!)

  • For me, it would be to have a kick-ass workout, followed by a hot shower, and then cozy up with a bottle of red wine and a good chick flick.

  • Celebrate as the Latinos do! In Latin America, Valentine's Day is known as "The Love and Friendship Day." Indulge in the other great loves of your life.

  • Bubble bath, meditation and favourite underwear day.

  • Spread the love in any event and share the love you'd like to have!

  • Love yourself ... I'll let y'all interpret that however, you like.

  • My best Valentine’s Day ever my girls and I went bowling, drank cheap beer and pigged out on greasy pub food!

  • WINE! No no....go out with your girlfriends and make it your intention to meet at least one interesting guy. Make it fun like a scavenger's a fun distraction and who knows what may happen!

  • Get together with friends, celebrate "anti-Valentine's" day by watching slasher or action movies, lol.

  • Go on a date with yourself...spend the day at an art museum, do a painting class, or go to the movies.

  • I have a friend that fosters her "inner man". She sees herself as already whole, yin-yang is already within you.

  • Romance yourself by making a lovely dinner at home, eating mindfully by candlelight and nice music.

  • Candlelight meditation. Sit alone and enjoy the company of your Self. The practice of self-love is very powerful.

  • I am using it to honour all of the healing work I've done. I'm subbing a class for someone in a super sweet relationship because I'm ecstatic to be where I am, not because I'm running (like I used to.) I'm so much more present now so that I know what I want as opposed to being caught up in codependency and hence reactive, mismatched love.

  • Collect your single girlfriends, host a 'singles only' dinner - followed by a night of dancing!

  • Show love and kindness to everyone you interact with.

However you choose to spend your day, I wish you a happy Valentine’s Day!



ps. If you have any other suggestions please comment below and I’ll add them to this running list!