This Month’s Featured Article

A hopeful romantic’s guide: Confronting tricky Valentine’s Day feelings & navigating a holiday dedicated to love

By Published On: February 3rd, 2025

When the month of February rolls around, the focus on romantic love can become overwhelming. I have spent all but one Valentine’s Day single, and whether I was surrounded by friends for a Galentine’s movie night, sick in bed while my flatmates made their way out to a London club, or spending an ordinary evening at home with family, I always felt a sense of yearning, as if something was missing.

Of course, it’s a no-brainer why that was. Rom-coms flooding television stations, pink and red hearts swarming every grocery store aisle, waiting with bated breath for a love note from a crush that would never arrive – everything related to this holiday promotes a feeling of longing to be in a loving, happy relationship. The expectations associated with Valentine’s Day are fun for some, giving couples a reason to spend quality time together and dote on each other, but for many, the celebration is difficult to digest.

What sort of negative Valentine’s Day feelings do people have?

It goes without saying that some single people aren’t a huge fan of the day. In “Does Valentine’s Day Even Matter?” for Coveteur last Valentine’s Day, Kelsey Eisen interviewed Shan Boodram at Bumble and Moe Ari Brown at Hinge to get to the bottom of the holiday’s intricacies straight from dating app experts. Both acknowledged that it’s easy to feel bitter or stressed out when Valentine’s comes along, but that celebrating the day and being able to stay hopeful about love is important.

Photo by iStock user Antonio Solano.

Psychologist Mark Travers wrote about prevalent sadness surrounding the holiday in “3 Reasons Why ‘Valentine’s Day Blues’ Are Real, From A Psychologist” for Forbes on February 4, 2024. As Travers explained, not only does the time come with a very intentional commodification – equating levels of love with grand (and expensive) gestures – but it leads people to feel worse about themselves and compare their love lives with the “curated displays” they see on social media or in real life.

In my experience, social media certainly provides a platform or two on which to commiserate, but it also offers that convenient, endless highlight reel of people in love for you to swipe through miserably. Certified marriage and family counselor Love McPherson wrote about this phenomenon in “Feeling Anxiety About Valentine’s Day? You’re Not Alone,” published on February 6, 2023. “For some singles (key word: ‘some,’ not all),” she explained, “February 14 is an annual day of self-defeating messages that reminds them: ‘You aren’t chosen! You aren’t worthy! You are not enough! Your clock is still ticking and you are still alone! You may always be alone!’”

Travers also highlighted the tendency to feel lonely on this special day even if you’re in a relationship or recently got out of one. Indeed, for those in a relationship, it doesn’t guarantee that you’ll have it easy; instead, everybody has opinions about the right way to treat your partner on the holiday, and according to Eisen, just about every variation of celebration (or not-celebration) can be interpreted as reflecting poorly on your relationship. Eisen said, “Clearly, all society seems to be able to agree on is that Valentine’s Day is some kind of barometer of your relationship; what they can’t agree on is how exactly that barometer is supposed to be calibrated.”

Combating the Valentine’s Day sadness

How, then, should people approach what can be a tricky, upsetting, and all-around bewildering day of the month? To Travers, beating the “Valentine’s Day Blues” can be accomplished through self-compassion, strengthening social connections, performing acts of kindness, planning ahead, and seeking professional support. McPherson recommended a similarly understanding approach, focused on celebrating the love we can give and receive, appreciating our loved ones, and fostering self-love. The antidote, then, seems to be nourishing those relationships you do have while reflecting the same gratitude and understanding back onto yourself.

Photo by iStock user Polinmr.

And what no one ever seems to talk about, of course, is that February also has many non-romantic, love-related day celebrations, including National Make a Friend Day (February 11), as well as Self-love Day and Galentine’s Day (both February 13).

I’m certainly no psychologist, and I don’t claim to have all the answers, but I think I’d like to elaborate on the aforementioned tips. While all of these suggestions are undoubtedly important and beneficial for developing and maintaining your mental health, something McPherson said is worth delving into a bit deeper.

Speaking about the meaning of Valentine’s Day and what it should represent, she shared, “It should be a joyful reminder that we possess the foundational ingredient that will determine the depth and width of all of our other love experiences. The truth is, self-love is the only love that we can control. Don’t deprive yourself of it. After all, we can’t expect someone to love us if we don’t generously show it to ourselves.”

Demystifying & clarifying self-love

This statement definitely has merit when you’re in a positive state of mind. But to me, when you get into a defeatist, self-conscious headspace about love, being told to love yourself can feel like the nail in the coffin, not the solution. It’s repeated so often it starts to feel intangible. And being told that you can’t expect to be loved by others when you don’t yet love yourself can make the whole ordeal seem even more impossible: not only does your singleness on Valentine’s Day breed bad self-esteem, but the bad self-esteem breeds singleness … so basically you’re screwed.

It wasn’t until recently that I began to reframe my relationship with romance – the daunting, all-consuming concept that it is – and understand a greater truth about what “loving yourself” actually means. I thought it could not be more timely reflecting on this revelation as Valentine’s Day approaches.

This enlightening realization was all thanks to my interview with writer, Interfaith minister, and entrepreneur Anne Kiehl Friedman, and my article about this discussion was published in last October’s Main Street issue. At the time of this talk, I was in a relationship, but for years before that, my dating history was rife with chasing dopamine hits and, ultimately, disappointment.

When I read Friedman’s book, Higher Love: a psychedelic travel memoir of heartbreak and healing, I fully grasped, for the first time, how to practice self-love in a way that didn’t feel disingenuous or ineffective. To Friedman, not only is love something you don’t have to work for, but it’s all about looking inside, not outside of yourself, to be known.

Photo by iStock user cagkansayin.

She explained to me that getting to know yourself – really know yourself – by asking yourself questions, spending time with yourself, and dedicating the same sort of curious energy to yourself that you might dedicate to someone you’re dating, is the key. Often, it’s easy to give all you can to someone else; arguably, it can feel more second nature than focusing on what you can give yourself.

Something that particularly stuck with me was when she explained that it’s not a matter of needing to love yourself in order to be loved, but that a lack of self-love leads you to settling for what you don’t deserve. Friedman described it like this: “There was a whole, and still is a whole, wealth of information about myself that I don’t know, that I’ve never asked, that I’ve never cared to ask,” she says. “If you don’t know yourself, you can’t be yourself. If you can’t be yourself, then any love you’re getting just doesn’t feel real because it’s not for you.”

While writing this article, I circled back with Friedman over email to share how she’d inspired me. In her brilliant way, she emphasized the importance of truly tapping into those things you wish someone else would do for you, and doing them for yourself. “Do you fantasize about someone planning a special fancy date night? Or writing you a gushing love letter? Or thinking you’re the sexiest person in the world?” she wrote. “Okay, how can you do that for yourself? You deserve someone who loves you enough to think about what makes you happy and give it to you.”

Getting concrete about those dreamy experiences and finding ways to provide them for yourself, Friedman added, clarify how you want to be loved by both yourself and others. “It doesn’t work 100% of the time or on 100% of fantasies, but I really believe we show people how to love us,” she said. “It made me realize what dysfunctional messages I’d been sending by withholding my own love and care.”

My recommendation, thanks to Friedman’s lasting and potent wisdom, is that if you’re single and unhappy, try to “date” yourself. When you start treating yourself with the same faith, compassion, and excitement you often shower upon others, you develop a firmer trust in yourself. With time, you might even love spending time alone, getting to know yourself and all that makes you special. If you’re dreading this month’s impending lovey-dovey-ness, I can’t think of a more fitting exercise to explore.

Cover photo by iStock user Sophie Popplewell.