My Funny Valentine: Hilarious Valentine’s Day Stories That Are Guaranteed to Make You Grin

Want to make your sweetheart smile? Check out the funniest Valentine's Day stories in Reader's Digest history.

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Valentine's Day stories - red plaid suit
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Funny Valentine’s Day Stories Shared By Our Readers

“As Valentine’s Day approached, I tried to think of an unusual gift for my husband. When I discovered that his favourite red-plaid pants had a broken zipper, I thought I had the perfect Valentine. I had the pants repaired, and gift-wrapped them. On the package I put a huge red heart on which I printed: My Heart Pants for You. I was the surprised one, however, when I saw the same heart taped to our formerly empty, but now overflowing, wood box. On it he had written: Wood You Be My Valentine?” — Contributed by Mary Lou Pittman

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Valentine's Day stories - honey
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Nuts About Love

“Driving through Southern California, I stopped at a roadside stand that sold fruit, vegetables and crafts. As I went to pay, I noticed the young woman behind the counter was painting a sign. ‘Why the new sign?’ I asked. ‘My boyfriend didn’t approve of the old one,’ she said. When I glanced at what hung above the counter, I understood. It declared: Local Honey Dates Nuts.” — Contributed by Theodore Bologna

Our kiss-and-tell exposes some fascinating facts about Valentine’s Day.

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Library stamp card
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Check-Out Romance

“I met my husband while I was working in a science library. He came in every week to read the latest journals and eventually decided to take out the librarian instead of the books. After a year and a half of dating, he showed up at the library and started rummaging through my desk. I asked what he was looking for, but he didn’t answer. Finally he unearthed one of the rubber stamps I used to identify reference books. ‘Since I couldn’t find the right engagement ring,’ he said, ‘this will have to do,’ and he firmly stamped my hand. Across my knuckles, in capital letters, it read NOT FOR CIRCULATION.” — Contributed by Ruth E. Chodrow

If nothing else, these cheesy pick-up lines are good for a laugh!

4 / 11
Couple texting
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Funny Valentine’s Day Stories, 21st-Century Style!

“My boyfriend and I met online and we’d been dating for over a year. I introduced Hans to my uncle, who was fascinated by the fact that we met over the Internet. He asked Hans what kind of line he had used to pick me up. Ever the geek, Hans naively replied, ‘I just used a regular 56K modem.'” — Contributed by Anne McConnell

Stumped on how to treat your sweetheart on Valentine’s Day? Whip up one of these easy Valentine’s Day desserts.

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Very Daring

“The lingerie store where my aunt works was crowded with shoppers selecting Valentine’s Day gifts for their wives. A young businessman came to the register with a lacy black negligee. My aunt noticed that the next customer, an elderly farmer, was holding a long flannel nightgown and kept glancing at the younger man’s sexier choice. When it was his turn, the farmer placed the nightgown on the counter. ‘Would you have anything in black flannel?’ he asked.” — Contributed by Christine A. Pandolfo

Check out the best rom-coms on Netflix right now.

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Bouquet of red roses
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9-5 Love

“My husband, a certified public accountant, works 15-hour days for the first few months of the year. In spite of his hectic schedule, he took time out to order me flowers for Valentine’s Day. While pondering what sweet endearment to write on the card, he obviously began thinking of the many hours of work still ahead of him. His note read: ‘Roses are red, violets are blue. If I weren’t thinking of you, I’d probably be through.'” — Contributed by Cindy Wolf

For more home-grown comedy, check out the best Canadian jokes of all time.

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Hands holding scissors
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More Than a Greeting Card

“My friend Mark and I work in a lawn-mower-parts warehouse. Somehow Mark got the idea that his wife did not want a card on Valentine’s Day, but when he spoke to her on the phone he discovered she was expecting one. Not having time to buy a card on his way home, Mark was in a quandary. Then he looked at the lawn-mower trade magazines scattered around the office—and got an idea. Using scissors and glue, he created a card with pictures of mowers, next to which he wrote: ‘I lawn for you mower and mower each day.’ Mark’s wife loved it. The card immediately graced their refrigerator door.” — Contributed by Gene Hyde

This marriage advice from the 1950s still applies today!

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Valentine's Day stories - woman shrugging
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Irresistible Irony

“About a year had passed since my amicable divorce, and I decided it was time to start dating again. Unsure how to begin, I thought I’d scan the personals column of my local newspaper. I came across three men who seemed like they’d be promising candidates. A couple of days later, I was checking my answering machine and discovered a message from my ex-husband. ‘I was over visiting the kids yesterday,’ he said. ‘While I was there I happened to notice you had circled some ads in the paper. Don’t bother calling the guy in the second column. I can tell you right now it won’t work out. That guy is me.'” — Contributed by Pat Patel

Here are 20 funny phrases that are worth memorizing.

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Heart-shaped box of chocolates
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Making the Grade

“My high-school English teacher was well known for being a fair, but hard, grader. One day I received a B minus on a theme paper. In hopes of bettering my grade and in the spirit of the Valentine season, I sent her an extravagant heart-shaped box of chocolates with the pre-printed inscription: “BE MINE.” The following day, I received in return a Valentine from the teacher. It read: Thank you, but it’s still BE MINE-US.'” — Contributed by Brad Wilcox

You don’t have to be a word nerd to find these thesaurus jokes funny.

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Read All About This

“Every Valentine’s Day our campus newspaper has a section for student messages. Last year my roommate surprised his girlfriend with roses and dinner at a fancy restaurant. When they returned from their date, she leafed through the paper to see if he had written a note to her. Near the bottom of one page she found: ‘Bonnie, what are you looking here for? Aren’t dinner and flowers enough? Love, Scott.'” — Contributed by Richard B. Blackwell

You won’t believe these funny news headlines actually ran!

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Bride and groom getting married
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Devoted and Determined

“During World War II my parents had planned a romantic Valentine’s Day wedding. Suddenly my father, then stationed at Camp Edwards in Massachusetts, received orders to prepare to ship out, and all leaves were cancelled. Being a young man in love, he went AWOL. He and my mother were married four days earlier than originally planned and he returned to base to an angry sergeant. After hearing the explanation, the sergeant understandingly replied, ‘Okay, okay!’ Then, as an afterthought: ‘But don’t let it happen again!'” — Contributed by Sandra L. Caron

If you enjoyed these funny Valentine’s Day stories, don’t miss our side-splitting roundup of wedding jokes.

Reader's Digest Canada
Originally Published in Reader's Digest Canada

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