Feeling Sad on Valentine's Day - Justin Lioi, LCSW - Brooklyn, NY

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It’s easy to be sad on Valentine’s Day whether you have a partner or not. Being alone can be difficult anytime, but this day can reinforce those feelings.

I remember a group of people in college who reclaimed it as “VD” day and they put pictures of crabs on their doors. It was a way to manage the anger and loneliness (although I imagine it didn’t make it more likely that anyone would date them.)

We’ve all got our ideas of what the perfect life would be, but often our ideas are not OUR ideas. They are the ideas that we’ve been watching on TV and hearing about in schools and our families forever.

  • You’re supposed to have a partner and go out and have chocolate and flowers on Valentine’s Day.
  • You have a wonderful mother and father who are still alive so you can celebrate them on Mother’s and Father’s Day.
  • You have a family that can’t wait to gather together at Thanksgiving and share a meal and stories of the year.
  • You must be absolutely happy, and constantly in song at the end of December.

If you aren’t for any of these things, then you need help, right? Something went wrong. Horribly wrong. You hear, “Have you thought about therapy or at least anti-depressants?” Why aren’t you in sync with the rest of America!

Or people poo-poo it all: No–it’s not all that great. It’s all commercialized. Don’t add to this! You’re letting the marketers win! I’m all for you enjoying yourself, even if that means putting up pictures of crabs on your door so you’re not sad on Valentine’s Day, if that’s what you’re really sure you want to do. Maybe that will get you through the day.

How (not) to Deal

Perhaps you just want to hide for a bit. Find a comfy couch and movie, maybe another single friend and watch Sleepless in Seattle again. Nothing wrong with that. Especially since Valentine’s Day is on a Saturday this year. It’ll be hard to even go out without being reminded.

But would all the marketing work if you didn’t, even a little bit, buy into this idea? Whether it is deep down or right on the surface, even if you didn’t want to go to Kay Jewelers, get a heart shaped Whitman’s candy sampler, and have a dozen roses delivered to your desk. If you’re feeling sad and lonely around this time of year it’s because you want something that you don’t have (even if you ostensibly do have it, but that’s another post).

Feeling the Feeling

Since this is a counseling blog and not a dating blog I’m going to say that one of the best gifts you can give yourself is to really allow yourself to touch on that wanting. Feel how strongly you’d like to be paired up and know that sadness, know that loneliness, know and feel the anger that you don’t have it. Pushing it away can give you a momentary reprieve, but you’re going to come back to it and it’s going to come out. Avoid avoiding loneliness.

Why not have a little say in how you have your feelings? They’re yours. Spend some time with them. Why let the loneliness get lonely? Do you think it’ll just go away?

People question me in sessions about this sometimes. “Why should I feel this way?” “What’s the good of crying, or getting angry?”

I take a breath because it can be difficult to see someone’s emotion that they are not allowing themselves to feel it. I take a breath and talk about how much work they are doing to defend themselves against feeling this. Owning that feeling. Saying: “Yes, I want someone to love me, yes, I want to be thought of and desired.”

It doesn’t make it magically happen, but it provides so much more space and takes a huge pressure off pretending it’s not there because they don’t want to look desperate in the dating world.

The next objection I get is, I don’t want to “wallow” in this feeling. I don’t want to be self-pitying.

I take another breath because the person who is so unwilling to have a feeling is often so worried that having that feeling will make them become like some other person they know who they are annoyed with for always making things about them.

It’s not as easy as you’d think to go from being the person who holds their feelings in to becoming the person who has no boundaries about how they feel all the time.

Wading In

In sessions there’s no forcing you to have your extreme feelings right away, right there. We don’t leap into the water right away. We’re more like my uncle who would enter a pool by putting his toe in, putting some of the water on his hair, maybe get his shoulders a little wet. It was sometimes comical to watch, but he had his process. He wasn’t afraid of the water, but he knew he had to get himself ready to go swimming. It’s what we do in session together. We put a toe, maybe an ankle in–how was that? We get to the knees, maybe that’s enough for today? Maybe that’s more than you’ve waded before. What was it like? Did you learn that you can go there and still be safe? If not, we go up the rung of the ladder again and see what’s needed to keep you feeling safe.

The point is there is a lot to feel and you’ve done a superb job of defending yourself against some emotions and all that can be uncovered at this time of year because being sad on Valentine’s Day is a thing we do here in America.

So the difference with this post and all the others you’ll read this week on this topic is I’m not trying to help you not be sad on Valentine’s Day. I’d like to make it okay for you to be sad. Because judging ourselves for feeling sad, lonely, angry, etc. is the opposite of helpful.

There can be something to be learned from that sadness. This is not a popular thing to say. We all work very, very hard to not feel the negative emotions, but I honestly believe they serve a purpose. Like the stomachache that tells us we’ve eaten too much or the pain of illness that gets us to slow down and see what we’re doing to our body, “negative” emotions (and, yes, I still use that term) point us to look at something.

Maybe your Valentine Day can be a time to reflect on what you want even if you don’t know how to get there just yet.


If you’d like more support in talking about difficult feelings, please don’t hesitate to contact me.

Justin Lioi, LCSW is a men’s mental health and relationship expert. He is a Brooklyn therapist (as well as also seeing clients online throughout New York State and internationally.) He received his degree from New York University and has been working with men and their families for over 10 years. Justin is on the Board of the National Association of Social Workers and writes a weekly column for the Good Men Project called Unmasking Masculinity. He can be found on local and national podcasts talking about assertiveness, anger, self-compassion, all with the goal of becoming the man you want to be.