• Naomi

The Worst Valentine's Date I've Ever Had

On a day where everyone is sharing all their glamorous dinners with their significant other or besties (can I get an amen for whoever coined #galentines 😅🙌🏻) I thought I would relive the WORST Valentine's Day Date I've ever been on and why I don't like to "plan to celebrate" Valentine's Day anymore...

It was like any other February 14th. Cold. Ugh, why is the holiday where you are supposed to get all fancy in a cold month? Some kind of precipitation spit from the sky...not quite rain..not quite snow...but it was much more dreary than sleet. That couldn't keep me down though. I had planned THE Valentine's Date of a lifetime for my boyfriend, Cory. Now there are two things you need to know before I continue on with reliving this day:

1. I LOVE SURPRISES! Any kind, shape, size, type, you name it. Except the ones that jump out from behind doors, etc. No scary surprises. Just the good ones. Anyway, Cory HATES surprises. But being the brilliant, thoughtful, creative, 20 year old girlfriend that I was...I knew he would love this surprise since I had planned it for him.

2. I don't plan things well. (Enneagram 7 here...if you don't know what that is, you should go take it now and we can talk about it...basically a 7 can be summed up in "buys plane ticket...figures out the rest later" 😂do you see where this is going yet??) BUT this particular Valentine's Day, I had planned out the date because I wanted it to be extra special. So I "planned" it.

My plan looked something like this:

Get dressed up super cute and take Cory to a movie and dinner at the Cheesecake Factory (two of his FAVORITE things).

What to wear? Check. What to do? Check. What to eat? Check. Boom. PLANNED IT.


So Cory picked me up from my dorm room where I had spent hours getting dressed, my roommates helping me do my hair and makeup, letting me borrow a fancy clutch because we were going to such a fancy dinner, only to be frustrated that it was cold and raining ice/snow of some kind. Now I had to put a coat on my super cute outfit. Oh well, this was going to be the best Valentines' Date EVER! Nothing could keep me down!!!

I had two "movie tickets" in my purse that I had made and snuck them into the glove box compartment of his car so it could be an extra level of surprise. *Word of advice for anyone reading this: if you are going to a movie on opening night, probably buy the real tickets first instead of paper ones JUST IN CASE it's sold out*

I was so excited I couldn't wait!! I put the GPS on to get us to the movie theater only to find out that movie had been sold out. SOLD. OUT. What?!! Like who goes to the movies on Valentine's Day!? Who cares if it is opening night! I was devastated. Slightly embarrassed (as I had bragged about how much I had "planned" this surprise date) But I shook it off. Oh well. We would just go to dinner and have more time there!

I told him where we were going so he could drive there and y'all...I could already taste that delicious cheesecake! Cory wasn't acting too excited, but remember he doesn't like surprises so I brushed it off as that. What Cory realized that I didn't....we were going to the Cheesecake Factory. On Valentine's Day...

We got out of the car and in out of the nasty weather and to my HORROR there were approximately 3,642 people waiting by the hostess stand. "It's okay," I thought to myself, "these are probably big groups waiting to be seated." On Valentine's Day. I approach the hostess stand with confidence, it was a Thursday night, and told her we would like to get a table for two. She looked up at me and said, "it's going to be a three hour wait."


Cory had staked a spot off to the side while I went up to put our name in, and as I turned to him, eyes welled-up with tears, he had the most handsome and at the same time annoying half grin on his face. I was furious. THREE HOUR WAIT. On a Thursday night?!??! I thought everyone would go out on Friday night!!! I was being creative! I had PLANNED this out!

He hugged me as I started to cry. There goes the hours of makeup. Being the wonderful supportive and amazing gentleman that he is, he tried to tell me we could stay and wait it out, but I was in no mood for cheesecake three hours from now.

We got back into the car and suggested we get something to eat. (I think he knew I was hangry and that was not helping the situation) So we got Chik-fil-A...from the drive thru...and went back to his house. We ate our Chik-fil-A in the basement over an intense game of Monopoly. Which he won. We laughed. We ate delicious food. And none of it was what I had planned.

That was 8 years ago, and I have refused to plan any kind of Valentine's Date ever since.

So I'm not anti-Valentine's Day, I just think there is so much pressure for a big romantic thing and I have never succeeded in this area. I have 2 other terrible Valentine's Dates gone wrong...maybe I will share one again next year 😂 In hindsight, that worst Valentine's Date ended up being one of my favorite dates once Cory took over the "plans". But this night was the night I decided I wanted to do my best to celebrate like Valentine's Day to love and respect him every day of the year.

To this day, we will still choose Chik-fil-A and board game over a night out on Valentine's Day.

Every time.

And Cory does the planning 🙈

xoxo, Naomi

(we do NOT have a picture from that Valentine's Date...shocker...so here we are on a day with warmer weather enjoying a vacation that Cory planned 😅)


 louisville, ky + worldwide

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