Managing Valentine’s Day expectations, whether you’re in relationship, dating or single

By Chantal Landreville, Certified Love & Relationship Coach and author of  Raise Your Love Signal: A Guide to Attracting and Keeping the Love of Your Life 

Ah, Valentine’s Day – the day when the air is filled with an overdose mix of love, roses and overpriced chocolate.
To be honest, I have not really celebrated Valentine’s Day since I entered into my current relationship. Surprising considering how I used to fantasize about the day when I wouldn’t have to hide as a single person or feel alone on this day. Ughhh, I dreaded this holiday every year!
Through my journey of finding love along with the work I do as a love and relationship coach, I’ve come to realize that I don’t need a specific day to define romance in my relationship. I’ve consciously chosen not to partake in the conventional celebrations. The excessive expectations that surround Valentine’s Day often leads to disappointment and unrealistic standards for success in relationships. We’ve been so Rom-Comed and Disney-fied that we lost the essence of what love really is about.
In my opinion, love should be celebrated in a broader sense, and beyond just romantic relationships. I prefer to focus on fostering love in various aspects of my life – with friends, coworkers, family, pets, mother earth, mentors and teachers – anyone that truly matters to me. Since then, I’ve transformed my relationship with our dearest V-Day. Why confine the celebration of love to just one day?

With all that being said, whether you’re deeply committed, dipping your toes into the dating pool, or happily solo, learning to manage your expectations around this holiday is a key factor for experiencing a day of bliss, or blues. Here are a few suggestions depending on your status.

Deep in Love:

Expectation Management: You’ve been together for a while, so the pressure to have a perfect Valentine’s Day can feel a little heavy. Here’s the truth: It’s not about the grand gestures; it’s often about the little things. Thoughtful things that maybe you used to do and stopped doing with time.  Your partner knows you inside out, a thoughtful gesture can be just as heartwarming.

Celebration Tip: Ask yourself this question: “What could I do that I never/rarely do that would make my partner happy?  Plan a personalized date that reflects a cherished memory. It could be revisiting the spot where you had your first date or recreating a favorite meal together. The magic is in the details that remind you both of the journey you’ve shared.


  • Leave sticky notes everywhere with compliments about your partner or flirty messages
  • Give each other a foot, back or facial massage; this is very intimate act and recreates connection
  • Get all dressed up and go out for dinner or have a chef come cook you both dinner at home

The Early Dating Stage:

Expectation Management: Valentine’s Day in the early stages can feel like navigating a romantic minefield. Do you go all-in with a grand gesture, or do you play it cool to avoid potential overwhelm? The key here is to keep it light, thoughtful, and not overthink it. It’s a day to celebrate the connection, not to overanalyze.

Celebration Tip: Opt for a casual yet charming date – perhaps a picnic in the park or a low-key dinner at a cozy restaurant. A small, heartfelt gesture, like a handwritten note or a thoughtful gift based on something you’ve learned about each other also goes a long way.


  • Play with a deck of cards that asks intentional questions so you can get to know each other on a deeper level
  • Take a cooking or painting class; this offers a fun and interactive way to bond while getting creative together
  • Have an indoor picnic, tossing away the furniture, setting up a cozy blanket, your favorite snacks and drinks; while a bit more casual, this offers an intimate experience


Expectation Management: Being single on Valentine’s Day doesn’t mean you’re banished to a deserted island. Instead of getting caught in the societal pressures, use this day as an opportunity for self-love and appreciation. Spoil yourself and do things that bring you joy!

Celebration Tip: Treat yourself to an experience you’ve been craving or that you wouldn’t typically give yourself permission to do – make it about celebrating your unique self and the love you have for yourself.


  • Write yourself a love letter. Start by listing 5 things you have accomplished in the last six months that you are proud of. We tend to focus on what we haven’t done and forget to celebrate our wins!
  • Buy yourself an amazing bouquet of flowers!
  • Treat yourself to coffee and breakfast in bed

Regardless of your relationship status, Valentine’s Day is an opportunity to celebrate love – not just the romantic kind but also the love you have for yourself and the connections you share with friends and family.

Manage your expectations by embracing this day from a different perspective that what we have been sold it’s supposed to be.  Remember, the most memorable moments often stem from simplicity and genuine thoughtfulness. So, whether you’re sipping champagne with your long-time love, or treating yourself to a solo adventure, let Valentine’s Day be a celebration of love in all its beautiful forms.

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