How to have the best Valentines Day of your life (with or without a man)

Don't get stupid over cupid!!!

Valentine’s Day is the single rose-scented pink puff of joy in an otherwise multi-month run of darkness, despair, and below freezing temps. A non-denominational holiday in the dead of winter that brings bows, hearts, and teddy bears to drugstore checkout lines and gives your local florist a boost in sales that will carry her into spring. What’s not to (sorry) love?

Regardless if my conversation heart says [x] taken or [x] single or [x] it’s complicated, I will always welcome Valentine’s Day with open arms because she’s fun and fabulous and, let’s be real, for the girls. So if you’re sad about being single for the occasion I am kindly suggesting a reframe for two reasons:

1. Pouting about it won’t change anything so you mind as well do a Sheryl Sandberg and lean TF in. A day of frivolity and whimsy awaits!

2. VALENTINES DAY IS ON A SATURDAY. Imagine wasting a Saturday in bed, doomscrolling and eye-rolling when you could be live laugh loving all over the place & celebrating all the love you DO have in your life. Love from yourself, your friends, your fam, your pet, your celebrity parasocial relationship, your bodega guy, your fictional book character boyfriend… Love actually is all around.

To get you ready, I’ve concocted a dreamy recipe of plans and purchases for you to make the most of this capitalist love affair. And if you do find yourself coupled up this year, everything will still apply! Just add your S/O to the plans OR dump them, whatever feels like it will bring you the most peace :) :) :)

5 ways to make the most out of your Valentines Day:

Write a love letter. Either to yourself, a friend, or the future lover you’re conjuring up. Valentines Day is all about romance and there’s nothing more romantic than honey-dipped words of affirmation! Keep it in your journal or if it’s addressed to a friend, send it via snail mail with a special stamp. To get you thinking…

Valentine’s Day Journal Prompts:

• What are three things I genuinely love about myself and why?

• Describe your perfect Valentine’s Day in extreme detail - who are you with, what do you do, how do you feel?

• What scents, colors, textures, flavors make me feel most like me?

• What are some of the qualities I admire in people that I love?

• Pick a song, movie, or book that gives you all the fuzzy feelings and explain why it feels special to you.

Take a level 10 everything shower (et al) the night before. You should be dolphin smooth and two shades darker with light discoloration on your wrists. You will have used all the devices you swore you were going to use every night in 2026!!!! (good time to revisit those self-care goals). By bedtime you should feel both disgusted by the amount of propaganda you have fallen for and purchased and delighted with how you’ve successfully marked yourself safe from the winter scaries.

Buy at least one traditional Valentines treat. Bottle of champs. Bouquet of flowers. A box of chocolates or other sweet indulgence. A snuggly teddy bear. Lingerie! Whatever tickles your fancy. Feeling ‘without’ is a crummy feeling (as a single girl I can relate, so trust that this is very sincere!). But I think what makes that feeling bubble up to the surface on Valentine’s Day is actually being without the STUFF. So don’t let yourself come home to a flower/chocolate/teddy-free house.

Make plans on actual Valentine’s Day. With a friend or with yourself! The rule is that your plans must be plans that require actual planning. We’re not playing anything by ear on a holiday weekend. I’ll be with my bestie at the ballet and afterwards we are enjoying an early dinner at a swanky french restaurant. Drinks will be drunk. Purchases will be made.

Some ideas…

• See “Wuthering Heights” and take a weed gummy before or sneak in a bottle of screw top rosé.

• Visit a museum that’s been on your list forever but you’ve never gotten around to it. Choose the guided audio tour. Eat at the café.

• Treat yourself to a unique self-care experience like a head spa or bath house. Tons of these on Groupon.

• Have a craft day. I am currently obsessed with bedazzling and love this hair clip idea!

• Workout class b2b matcha/iced coffee b2b light shopping and lunch. Name a better day.

Dress like you’re going to spend the day with the love of your life. For starters, you should be one of the great loves of your life. And I don’t mean that in a self-indulgent way, quite the contrary. You spend 100% of your time with yourself so you mind as well start loving the shit out of her. Second, if you believe in the power of manifestation, then you know that embodying your future is kinda the whole whole thing! Get ready intentionally. Wear something that feels like the best version of you. I would suggest wearing pink or red but I know that my threshold for kitsch is higher than most so I give you space to wear whatever makes you happy.

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And there you have it, a Valentines itinerary so sweet you might actually romanticize being unattached at this moment in time!

xx Caylee

Thank you for reading! If you enjoyed this piece you may also love Poor little single girl :( and 33 Lessons in Girlhood.