Readers share their stories of unforgettable first dates, from studs to duds
12 of the Sweetest and Funniest First-Date Stories You’ll Ever Read
Published on Jan. 23, 2025
What was your most memorable first date? Was it a whirlwind of fun and romance or an unforgettable disaster you still laugh about today? If you’re someone who loves tales of true love and the magic of beginnings, you’re in for a treat! We asked our readers to share their most unforgettable first-date stories, and they’re as charming as they are relatable.
From a semi-romantic ski trip in the mountains to an adventurous hike and even a bold first-date question right in the middle of a classroom, these real-life stories are sure to warm your heart.
So dive in to these sweet, funny and inspiring first-date stories. We guarantee they’ll have you reminiscing about your own first date with your partner in crime.
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Love at first flight
My cousin had been boasting about her husband’s tall, handsome, single flight instructor for a while. It turned out Bill is quite shy, so when he finally asked me out, he really wanted to impress. He picked me up to go to the airport, where we boarded a Cessna 172. We flew from New Jersey to Connecticut, landing at an airport with an excellent restaurant. We flew to Pennsylvania for dessert. Then we flew over Manhattan to marvel at the lights and Empire State Building. When we landed, my head was spinning with excitement, and I knew we’d be together for a lifetime. —Lois Klotz, Englewood, Florida
And the class goes wild
This is more about “the ask” than the actual date. My future husband and I taught at a large high school. One Friday afternoon, I had 10 minutes of a lesson to go when he knocked on the classroom door. I looked at him, confused. The class went silent. “I was wondering if you wanted to go to dinner with me,” he said. I said, “OK,” and the class began clapping, whistling and yelling. When he left, my students wouldn’t stop asking questions. Needless to say, no more learning happened after that. —Jan Roland, Wabash, Indiana
The apple of my glass eye
In the 1970s, my date and I were at a disco when a woman dancing nearby was spun by her partner. The quarter-size plastic beads affixed to her long ponytail whipped my date in the face—and popped his glass eye out. He quickly pulled an eye patch from his pocket and chased his eye across the dance floor. —Christine Tunanidis, Port Richey, Florida
Certified dad-approved
My parents agreed to let me go on my first date at age 16. Dennis arrived on time, but before he could make it to the front door, my dad intercepted him. I watched from the porch as Dennis helped unload drywall panels from my dad’s truck, waiting until it was all neatly stacked in the garage. —Sandra Squire, South Charleston, West Virginia
Tour de Florida
On our first date, we took my VW bus 25 miles into Everglades National Park and rode bikes more than 6 miles to a scenic fire tower … at midnight under a full moon. We’d been introduced days earlier, and I hoped she’d be adventurous (and trusting) enough to say yes. We rode our bikes through the park again in our 30th year of marriage. We’d missed the full moon by two days and midnight is too late for us now, but we did catch the sunset at the fire tower. It was very emotional to be in the same place 30 years later, still in love and crazy enough to bike a 13-mile round trip at night. —Sid Bird, Lee, New Hampshire
A “double” date
We met at a cafe, where I ordered an herbal iced tea. He ordered the same. Then we caught a movie, where I ordered water and popcorn with light butter. He ordered the same. At dinner, I ordered the strangest meal I could think of: lemon meringue pie and hot cocoa. Sure enough, my date got the same. No second date, but I do wonder where Echo Man is these days and if he still mimics his companions. —Lois Shaffer, Blythe, California
Dating the whole family
I was raising my sons, just the three of us, forever. Everyone at work thought I was a perfect match for one of our colleagues, but I rejected the idea. A year later, he asked me on a date, and I said yes. He ordered pizza and found a babysitter for my boys, then took me out for a steak dinner. From just one evening, I knew our co-workers were right. —Deborah Stranahan, San Juan Capistrano, California
Partners in crime
Joan was born in Toronto, and I in Buffalo. Our first date was in February, so I asked her to go tobogganing. We went to a golf course and slid down the hills. Security raced toward us on snowmobiles, but we buried ourselves in the snow. By the time they made it to us, we were completely hidden. We’ve been married for 50 years, even though I’ve proved correct everything she’d ever heard about “crazy Americans.” —Richard Winger, Valencia, California
Giving each other some space
My wife and I went hiking on our first date, but I got us lost, so we had to bushwhack for a bit to find the trail again. As she forced her way through the brush, she pulled aside a sapling and released it, unaware of how close I was behind her. It smacked me in the face, and blood poured from my nose. She felt horrible, but I wasn’t too badly hurt. We still go hiking 41 years later—but I walk a bit farther behind her now. —Wayne Sanders II, Akron, Ohio
A total snooze
My date picked me up and took me to a play in which he was performing. I was taking aspirin that made me drowsy, and when I went to the restroom during the first act, I fell asleep. I woke up when other theatergoers came in at the end. I hustled to meet my date backstage as quickly as my numb legs could carry me. He asked how I liked his performance, and I told him he was wonderful. Had we known each other better, I’d have come clean, and we’d have had a good laugh. Ronnie, if you’re reading this, I’m sure the play really was awesome. —Cindy Sidell, Lufkin, Texas
Ain’t no mountain high enough
I met Dale on a ski lift in Oregon. We skied together until I fell, at which point he threw his business card on the snow, informed me his bus left in 10 minutes and took off, leaving me sprawled face-down. Not long after, I persuaded him to join me in scaling the 11,239-foot Mount Hood. We reached the summit in some of the best weather and snow you can ask for. We got married and have been skiing and climbing mountains together for the past 50 years. —June Wyman Helbig, Vancouver, Washington
Undress to impress
He was a veterinarian who went to church with me. When we got back to my place, my neighbor was waiting. “Doc,” he said, “my cow is in labor.” I tagged along to the barn next door. “Doc” was wearing a three-piece suit, and there, under the car beams that we pointed into the barn for light, I watched him strip to his underwear to protect his nice clothes and deliver the calf. —Norma Boyd, Savannah, Tennessee
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