It’s Okay To Hate Valentine’s Day

Dear SMP Community:

I’m a dating coach and I hate Valentine’s Day.

Since I started Style My Profile over three years ago, I have been asked each year to talk about Valentine’s Day at some point. And although I am a huge fan of people finding love, I kind of hate Valentine’s Day.

I’m not even sure when my dislike for V-day started, but it was well before being dumped many times when I was young, before getting married then divorced, then being single for years after that. And now even being with someone awesome, I still don’t like it. The obvious reason is it’s a forced Hallmark holiday. But for me, I’ve come to realize, it’s more about how it makes everyone feel. 

No matter what, if you’ve grown up in a culture that celebrates this “day of love,” you feel let down somehow. Whether you’ve just begun dating someone and then V-day looms over the new relationship like a big question mark, or you don’t know how or if you should acknowledge it even after dating for several months, or you haven’t dipped a toe into the dating world in a long time, Valentine’s Day can feel daunting no matter what your situation. And forget about getting a restaurant reservation unless you plan way ahead of time. Valentine’s Day generally makes people feel inadequate.

If you are newly separated or newly single after a break-up, then you may even be dreading Valentine’s Day this year. It feels like a way of drawing attention to how not in love you are.

When I was first separated, I actually went on my first real date on February 14. Other than giving my two daughters chocolates every year, I was someone who hadn’t celebrated Valentine’s Day since I was in high school with my first boyfriend.  After texting with my potential date for a few days, he and I decided on meeting up for coffee that Saturday afternoon. It wasn’t until I looked at my calendar that I realized that it would be Valentine’s Day. I said something to him when we spoke next on the phone and he told me he wasn’t a big Valentine’s guy anyway so we chose to ignore it. Which went rather well actually (the part about ignoring V-day, not the date—I was a nervous wreck!).

If you are newly single and considering getting out into the dating world, I know it can feel nerve-wracking. And especially if, like me, you’re beginning to date around Valentine’s Day, it can feel daunting to know how to handle that. The best advice I can give you is to first decide whether you are up for a date on or around Valentine’s Day when it could put undue pressure on the date. Whether it is a virtual date or an in-person date, it can make the already shaky moment of a first date feel even more so. Secondly, if you decide you are ready for that, you should acknowledge the holiday with your potential date and possibly make a joke about it. You never know, it could be an ice breaker. 

That all being said, if you do truly enjoy this holiday, as I know many people do—no matter what is going on in your relationship life—that’s amazing. I hope you can enjoy it whether it’s with your best friend, your mom, your child, or… your date for the night. Just be sure to make your dinner reservations in advance!



I want to invite you to sign up for the Mindful Dating Workshop, where you can learn through instructional videos and a Dating Diary everything from deciding whether you’re ready to online date, to how to turn someone down (nicely), to how to talk about sex and intimacy. 

Or, sign up to become and annual Dynamic Dating member and get access to the Mindful Dating Workshop PLUS monthly live Q&A’s with me, access to shopping discounts and seasonal shopping guides, AND guest experts like world renowned hair and makeup artists, photographers discussing selfies, sex therapists and more.

Need help with your online dating profile? Schedule a consultation to learn more.

And if you’re a previous SMP client, click here to find out about date coaching!

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Hi! I’m Alyssa Dineen and I’m a personal stylist and dating coach all rolled into one. I started Style My Profile to help other online daters feel better about getting out there— and staying out there— in the world of online dating. Whether it’s to meet your soulmate, to find a fun person to have dinner with or even just match with more people, I can help you from the ground up.


dating profile in an hour course


Purchase our Profile In An Hour, designed for getting your profile swipe-right ready in as little time as possible.

The One and Only DIY Profile Kit
The Virtual Profile Makeover
Profile In A Day
One-on-One Date Coaching