Funny Valentine’s Day Stories & A Giveaway

Funny Valentine's Day Stories & A Giveaway

I’m starting to get that heartfelt feeling.

New Year’s resolutions, now long forgotten, have moved over.

Romance is hitting the stores and Valentine’s Day is everywhere.

It’s much bigger than a Hallmark moment. It’s a collection of the funniest experiences, stored in our mind like a “Jack in the Box” ready to boast.

It was the best of Valentine’s Day and the worst of Valentine’s Day. It was the age of “Oops, I think someone blew it!” when I asked a group of people to share their best and worst Valentine’s Day gifts. What came next was, of course, side-splitting, chuckle-some, and uproarious recollections:

My Funny Valentine’s Day Story

A long and creative time ago, I decided to surprise my husband with the best imaginable gift for Valentine’s Day. I just found out I was pregnant and decided to surprise him during a Scavenger Hunt (a game in which a series of clues brings you to different locations until finally, at the last location, the prize is found.) At the end of the hunt, I had 3 envelopes. He opened one and it said, “Maybe it’s a girl.” The next said, “Maybe it’s a boy.” But before he got to the 3rd envelope announcing, “Guess what? We’re having a baby!” he turned to me and shouted, “G-d damn-it, don’t tell me you’re getting another dog?”

“Hmm,” I thought, what did I miss here? It was clear to me—how much clearer did I have to get? Fun and different and scavenger hunt gone astray, I vowed that from now on I was returning to the basics and while I was at it, I’d get another dog.

Funny Valentine's Day Stories
Rub a Dub Dub

“Mine weren’t bad and they weren’t good”, said a friend. “They were exactly the same every year. A bubble bath and body lotion. For 20 years. A little vanilla here a little lavender there. And, I always smiled and acted surprised.”

The Good the Bad and the Ugly

“The best was a day hike to a hidden waterfall in the mountains of Colorado. Then a few hours at an outdoor hot spring called Manitou Springs in Glenwood Springs, Colorado. The worst was a Chia Pet – seriously.”


“I don’t really remember any Valentine’s gifts, except one: pajamas with hearts about five sizes too large.”

The Dreaded V-Day

“When I was a married man, Valentine’s Day was a nightmare for me. One year I gave my wife a new bicycle but she wasn’t too enthusiastic about it. But my biggest fumble was giving her an assortment of premium flavored coffee mixes. I thought she’d like it because she loves coffee. I was very, very wrong. We’ve been divorced 8 years and she still won’t let me forget it :-)”

Honesty Helps

“I have given socks (cute socks, but maybe not the best gift for a guy to receive). I have a particular dislike of red roses, so I can’t say I’ve been terribly appreciative of red roses I’ve received on Valentine’s Day (though that’s not really a fair one). Best gift? (After hearing and remembering that I don’t like red roses) Purple Irises.”

What’s With Red Roses?

“I really never got a Valentine’s Day present!! Red roses were the worst, I hate that color, but he stopped that. Another was bad candy from Walgreens. The best is what I buy for ME!!!”

The Heart and Soul of it

“OK, Valentine’s Day is kind of a non-holiday (retail has damaged me), so it’s not especially important to me if I get a fancy gift but the worst: a stuffed teddy bear holding a heart that says, “Be Mine”. Yuck! The best: an anatomically correct heart necklace. I loved it!”

Sexy does it

“It’s an easy one: the worst gift was the first year my husband and I were dating: an electric broom! (I mean, really!?) Next year he wised up – a beautiful pair of earrings! Another year, he bought a great set of sheets (I know, but they were like a 900 thread count – silky, luxurious, sexy!)”

Funny Valentine's Day Stories
Don’t Hide the Key

“I think my best was a pleasant surprise – I came home and found an ex-boyfriend had come in (he had a key) and set up flowers and candles all around the room.”

School Days

“I remembered receiving a lovely romantic note from a boy I liked very much in Junior High School. I must have read it a million times!”

Do Unto Others

“I would say my worst gift was no gift from a man I was dating. No card and showing up late to the restaurant to boot! On two other occasions, I was also disappointed by yet another two men I was seeing. Why? They each got me a box of chocolates when I had bought one a $300 leather jacket and the other a box of boxer shorts.”

How Lucky Can One Girl Get?

“The best valentine gift I ever received was a pair of diamond stud earrings. The worst? I never received a bad one, lucky me!”


“One year the kids wanted to do a Secret Santa version of Valentine’s Day. We all drew names and then bought little trinket gifts that we would secretly give to our Valentine for 3 days before Valentine’s Day. My husband had no idea what Secret Santa was so he bought 3 packages of M&Ms and gave the same gift every day.  Obviously, he was “Ousted” on day 2. No female would have given the same thing each day!  We repeated it other years and he stuck with his M&M system…. what can I tell you?”

I’m Gonna Marry Him, Marry Him!

“I don’t even remember getting a good or bad Valentine’s Day gift. Why?? Because, I was single for about 12 years. Last year my boyfriend and I broke up literally on Feb 15th for 3 days. So, I decided that this thing would NEVER work out. I guess you can say that was the worst gift ever. I cried to all my friends. Mind you, I don’t ever cry. That’s when I realized that I really loved this fool. And by day 4 we were back together. It’s been over a year now and I’m positive that this is my last stop. I’m gonna marry this guy!”

TIPS for a SUCCESSFUL 2020 Valentine’s Day

  • Don’t – Give day-old grocery flowers.
  • Do – Have a budget and make it the nicest flower arrangement or gift you can afford.
  • Don’t – Give a pen.
  • Do – Make it intentional and write a message from the heart.
  • Don’t – Buy lingerie without knowing.
  • Do – Know the correct size before you make that purchase. (A little sexy and a lot of insulted don’t work well together.)
  • Don’t – Spend too much.
  • Do – Have fun and write caring messages that you tuck away in their “go-to” places (drawers, coat pocket, make-up bag, etc.)
  • Don’t – Panic.
  • Do – Dare to be different. Every woman and man wants to feel loved and special. Serve breakfast in bed. Or be VERY daring and create a “Wish” day. Just be prepared.
  • Don’t – Let one day define your relationship.
  • Do – Reflect. The gift is in what happens every day throughout the year.
  • Don’t – Forget.
  • Do – Enjoy and make the day count!

Make Valentine’s Day Even Better with Real Home Innovations


By winning some prizes for you or your loved one, of course!

I’ve teamed up with the homeware experts at Real Home Innovations to create a Valentine’s Day Giveaway bundle just for you!

Real Home Innovations are superstars in the industry and create the most remarkably clever home organization products. Each item is handier than the next. Best of all, these useful products are designed not just for practical use but for style too. Spruce up your home this year by getting your hands on organizing products that are ideal for busy people who just need some extra help. One of the most effective ways of getting organized is using the tools available to you and we want to give one lucky participant a bunch of new tools this Valentine’s Day.

Valentine’s Day Organizing Bundle Giveaway

So, whether you want to spoil yourself (you know exactly what you want after all) or you want to help simplify the life of your special someone, The Organizing Confessions Valentine’s Day Giveaway will help you do just that!

Real Home Innovations have helped me put together a huge bundle of organizing products – here’s what you can win:

  • 4x Clear Handbag Protectors in various sizes ($54) – keep your handbags dust-free and in excellent condition while neatly packed away.
  • 1x Single Tier Aluminium Dish Rack ($40) – with an elegant design this durable dish rack fits nicely on your kitchen counter.
  • 1x Two-Tier Aluminium Dish Rack ($50) – with an elegant design this durable dish rack fits nicely on your kitchen counter.
  • 1x Expandable Over the Sink Aluminium Dish Rack ($25) – with a modern design, this rack is great for all kitchens.
  • 1x Deluxe Cushioned Sink Mat ($10) – protects sinks from scratches and keeps fragile kitchenware safe while washing.
  • 1x Over the Sink Drying Rack ($20) – this roll-up design is stable yet soft and the ideal item to save space in the kitchen.
  • 1x Deluxe Dish Soap Dispensing Scrub Brush 2 Piece Set ($13) – guaranteed to remove grease and grime from your dishes and non-stick cookware.
  • 1x Deluxe Dish Soap Dispensing Scrub Brush 3 Piece Set ($13) – the ideal item to tackle even the toughest cleanup jobs.

The Valentine’s Day Giveaway Details

The total value of this prize is $225 – definitely a superbly valuable Valentine’s Day gift idea!

Each of these organizing products can be found in top home goods stores around the country and are of the finest quality.

All you need to do is click this link to head on over to the giveaway page.

Enter your details and submit them.

That’s it; you’re in the draw to win the big bundle of organizing goodies!

Want an even better chance of winning?

That’s easy!

After you submit your details you’ll be directed to a page where you can complete various actions (like sharing the giveaway or commenting on this blog post) to get more entries.

The more entries you have, the better your chance of winning.

Good luck!


Comments 68

  1. We don’t really do gifts, although my husband usually gets me flowers. I just heard someone talk about writing a love letter to her husband, and I thought this was a terrific idea. We do enjoy going out for dinner, but usually avoid Valentine’s Day proper because it often is a bit more pricey and a limited menu on this day. I love your list of suggestions!

    1. I’ll never forget when I was a little girl, my mother gave me the most beautiful Valentine’s Day card. There was a big heart on the front of the card filled with red hot candies. I just loved that and still remember!

  2. That’s an incredible mix of gifts. I can’t recall getting or giving Valentine’s Day gifts — I’m more likely to go all out for a birthday celebration. But the person who gave the electric broom definitely some extra sensitivity training! My father used to buy day-old flowers in his office lobby and day-old candy, ostensibly for my mother, except he’d eat it all. Perhaps a well-meant electric broom isn’t so bad! 😉

    1. I guess we just have to have a sense of humor about those Valentine’s Day gifts. A beautiful card says a lot. I remember one year, instead of little gifts, I wrote to each of my children telling them how special they were to me.

  3. I will openly admit that while I get that Valentine’s Day is a commercial holiday, I LOVE it! I always have. My mom and dad always made it special. I’d wake up and at the breakfast table I’d find a construction paper heart with a pocket containing a loving message and a Nestle’s Crunch bar. My parents always exchanged valentines with each other. And I remember spending time making Valentines with glitter, glue and more for my classmates.

    Fast forward into adulthood and the tradition continued. I always enjoyed making Valentines for and with our daughters. And I’d make a special Valentine’s Day breakfast with chocolate waffles with fresh strawberries or berry muffins. My husband knows how much I love this holiday so he’s always helped me celebrate and feel very loved and appreciated.

    What can I say? It’s the day of love. And while we love 365 days a year, it’s the one day that I spend more time than usual basking in all the pink, red, sparkles, chocolate, loving messages, and deepest gratitude.

    1. I just love this. From all of your stories, it sounds like you have amazing parents and such a loving husband. I know you have a wedding coming up. I just bet you your daughters continue the tradition with their own families.

  4. awesome gifts ..usually just stick to flowers and candy ,but u have gave me new ideals ,thank u

  5. The only Valentines Day gift I remember was a pin with two hearts and lots of glittery stones that my parents gave me when I was a teenager. My mother said it was expensive (probably meaning it was $10 when the others were $7) but my father really wanted to get me this one. I still have it. 🙂

  6. I, for one, would have loved the assorted coffees. My husband (when we were dating) once gave me a coffee grinder and a beautiful mug and I thought it was great – even though my friends thought it was weird. I still have both – 25 years later.

    1. Your husband sounds like a dream boat. He got you something that he probably knew you’d love!

  7. What a great post! I loved reading all the stories. And I too would have been fine with the coffees! This made me think back over all my valentines days and they have all been wonderful (maybe because I would love coffee rather than nothing at all!). But the best were the very valentines when we did valentine day card sharing at school. Such a rush to see that my 5th grade crush bought me a big card and actually did sign it Love, David. I remember the tingles still! lol

    1. I remember those days too and making sure I had enough for everyone in my class. It was so much fun handing them out. And waiting to get one in return.❤️

  8. I can remember the days when I was more organized. I long for them! This is my New Year’s resolution. So far, so good!

    1. Dana,
      “So far so good” is absolutely fine. You are doing what you can and when you can do more, you’ll do more. What’s important is that you’re steady and getting things done.

  9. I love your scavenger hunt story!! SO funny! I think my husband would have probably reacted in a similar way.

  10. My husband and I exchanged vows on Valentine’s Day twenty-three years ago. Gifting for both on the same day can lead to getting the same type of gifts often and sometimes feeling annoyed. It’s helpful to get new ideas! I have a 9 and 11 year old that love to craft so I’ll definitely make use of these tips.

    1. One year I gave my children letters about how much they mean to me and why. They loved them.❤️

    1. Really? I am a total romantic. I always have been and I guess I always will be. It must be the Capricorn in me. 🥰

  11. Awww…. That’s so sweet yet full of fun blog post. My husband usually prefers bringing flowers on Valentines – The Pink and White ones <3 Those are my fav

    1. It takes time to build a new skill. Any skill. I have other articles on my blog that have great ideas for getting organized!!

    1. I have so many great tips on my blog and on my Instagram page. You CAN get organized. One step at a time. I wrote about that in the most recent article on why it’s so hard to get organized.
      Good luck!!

  12. BEAUTIFUL story!! Very happy for you and your family!! I’m not well organized at all. I need your advice!! I just gained custody of my granddaughters so this organization would be soooo helpful!!

    1. Hi Danielle,

      I’d love to help you. I’m a grandma too! I’m not quite sure which article you are referring to here, please let me know. I also have many great tips in my blog posts for getting organized.

      Let me know how I can help.


  13. Keeping it simple and fun has always worked for us. Remove the pressure and expectation and just do a few small, thoughtful things which conveys the message of caring.

    1. Keeping it simple and fun sounds like the best way to go. Have a terrific Valentine’s Day!

  14. Oh, dear— another dog! :p Loved your blog post and anecdotes.
    I’m terribly in need of better organization. Even after all those years in graduate school I still don’t have a real workspace, or even a desk. I’ve got ADHD, and the signs of it are all over if you look closely: hurried little notes, lots of notebooks, and so on. Just a general, and very frustrating, lack of organization.

    1. Actually having a dog or two can help get you organized. They’re on schedule, when they go out when they eat.
      I bet if you look around your home you might just find a great space to work. You can turn an empty closet into a work space, a spot near the kitchen, in your bedroom or off the beaten track. It doesn’t have to be large, just comfortable. With good lighting and a sturdy chair, it may begin to help you feel more organized.

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