50 Stories of First Dates That Went Well


1. “My first boyfriend was in 7th grade and for our date he took me to the stables he worked at and let me pet the horses, which is absolute gold if you’re a 13 year old girl like I was lol.”

2. “Dude took me to lunch. Went well so we went to the beach right after, even though we weren’t dressed for it. We went kayaking on a whim. Saw a sea turtle, jumped off into the water with our clothes and everything to chase it. Then drove me home on his motorcycle with our clothes still soaking wet.”

3. “My first date with my partner involved us sitting on a park bench watching people fall off of skateboards”

4. “We went to the science museum! Hours of walking though the various exhibits and talking about nothing in particular, it wasn’t very luxurious but it was heaven spending time in my favorite museum with someone special.”

5. “Believe it or not, the dog park. We were both students living in the dorm that doesn’t allow pets. It was a perfect afternoon, breezy and sunny, laying on the grass and petting all kinds of dogs!

6. “Giant flea market. (There’s one a few towns over and it’s ENORMOUS and full of cool, cheap treasures you can haggle over.) She was an awesome negotiator and every time she bought something, she and the seller were left happy. Plus, we could suss out how high-maintenance the other was (not at all) and find a million things to laugh at, like the woman who wouldn’t sell a Burger King kid’s meal toy to ‘Nicola’ because Nicola said it’d be perfect for her puppy to play with … (lady thought it was too good for a dog to just chew on, but only valued it at a quarter) … or the guy with the Beanie Baby stand who told us as we casually walked along that he’d ‘take $40k’ if we wanted all of them.”

7. “First date was second hand book shopping and coffee. My 2 favourite things to do, and his. Then amazing conversation.”

8. “I met him at the Queen Vic Markets midday on a Saturday. We wandered around looking for fruit to make jam, bought interesting delicacies in the deli, and custom-ground coffee. Then we trammed to his house and sat on his balcony drinking coffee and eating halva and turkish delight and talking for hours before we actually went downstairs and made the jam with a record playing in the background. While the jam cooled we sat upside down on the couch giggling like little kids before I asked him to show me his guitar. He was super nervous but played a bit of Just Like Heaven by The Cure for me before admitting that he had a huge crush on me and officially asking me out. Spent about nine hours together that day and we’ve been peas in a pod ever since.”

9. “We were sitting next to each other in the library at college fairly late in the evening and some other kid was making a scene, just really being very loud and making a fool of himself. We bonded over laughing at his ridiculousness and right before the library closed he turned to me and said ‘Would you like to go on an adventure with me?’ We ended up taking a stroll to a nearby elementary school and goofing around on the playground equipment before making our way back to the college campus. This is in Oregon so there was this beautiful walkway by a creek (we took the long way back), and we ended up climbing a tree that hung over the water. We sat on it next to each other with our feet dangling over the water and had our first kiss.”

10. “We met in a park near my place and walk around a bit and he told me ‘hey, since we’re in this neighborhood and so close to the airport, wanna go watch airplanes land?’ he asked. ‘aaahmm. Sure?!’ I responded, thinking that next time I should propose a cafe. We walked for around 20 minutes until the spot he had in mind, and I was thinking how can I escape this fast, without being impolite… But we had the most amazing time watching airplanes landing. I was surprised that so many people were there and enjoying the show. Most of them brought snacks! I had so much fun just sitting there and talking and guessing the stories of the people who were next to us.”

11. “The first real date I went on, my date got us tickets to the Trans Siberian Orchestra. Christmas is my favorite season, and the concert was beautiful. Still my all time favorite date.”

12. “We had matched on tinder, exchanged numbers, and had been texting for about 2 weeks. I was working on homework in the library when he texted me saying that he was getting a burrito and asking if I’d like him to bring me a burrito. Obviously I said yes, because free burrito. He brought the burritos to the library, and we sat together and ate them and really hit it off. About halfway through the burrito I got on my phone and cancelled the plans I had for that afternoon so I could spend more time with him. I would say the main things that made it such a great first date for me was the spontaneity, the fact that we hit it off immediately, his kind gesture of bringing me a burrito, and obviously the burrito itself.”

13. “We went on a 30 mile bike ride, during which we stopped at vineyards and a brewery. It was awesome because he knew I was into biking and he wasn’t. To prepare, he’d bought a bike and started riding to get in shape. The effort was really cool.”

14. “I met this guy on Tinder and was living in Southern California at the time. He wanted to go on an adventure, as did I. He picks me up and we drive to Tijuana Mexico. I didn’t have my passport with me but he did. I kid you not, I got in and out no problem. We spent the day sight seeing the beautiful ocean views. We rode horses on the beach. Got amazing street tacos. He gets a call saying his buddy’s funeral was in a few days all the way in St. Louis Missouri. He says he needs to go and asked if I wanted to drive with him. I do. This first date turned into a 3 week cross country road trip.”

15. “I was living in NYC at the time – about 15 years ago – and this guy took me to an interactive play. For the life of me, I can not remember the name of it. You stood the whole time and were shuffled around while the action took place around you. It started with paint falling on massive white sheet of paper above the crowd to simulate rain and then the actors literally bungee jumped through the paper and would grab people in the audience. The actors ran up and down walls (on wires) and there were strobe lights, actual water to simulate rain, music, and all kinds of craziness.”

16. “We went to a botanical gardens while it was raining and chatted for hours. He was a great swing dancer and taught me how to dance while it was raining. Made a move at the perfect time. Just a really lovely first date”

17. “First date was to Chipotle. I ate all of my burrito and he was only halfway done with his. I asked if he was going to finish it and he gave it to me and watched in horror as I shoveled it in. We’re married now.”

18. “While in college a guy I had been talking to over the summer asked me to dinner at his place when school started in the fall. He cooked us a pasta dinner, then afterwards suggested a walk around campus. Our campus was small but beautiful and we chatted about this and that as we walked, and ended up in a little alcove of benches surrounded by little bushes. We sat there talking for at least two hours, despite the fact it was September and chilly. Neither of us were very social people, but somehow we never ran out of things to talk about. When we finally decided to part, the guy turned around and pulled a bouquet of roses out of the bush behind him. He had planted them there (no pun intended) earlier that day.”

19. “My current boyfriend took me on our first date by piloting a plane on the 4th of July. We circled fireworks going off and then got ice cream. It was amazing.”

20. “We met online. After a week of talking, we met for coffee and chatting. That “one hour” date turned into eight hours of great conversation and two restaurants.”

21. “We were supposed to go to a concert but it was cancelled at the last moment. We ended up still meeting up for dinner but then were at a bit of a loss for what to do next so we wandered into a nearby toy store and discovered we both thought LEGO was really cool we got a couple small sets and blind mini figure bags and went back to his place to drink wine and build LEGO. I ended up staying for most of the night because it was just fun and playful and wonderful.”

22. “He picked me up and we went to a really cute hole in the wall restaurant. The waiter forgot to split the check so my date paid. I felt so bad that I told him we should stop for coffee, my treat. We ended up sitting in the coffee shop for three hours and only left when it was closing time.”

23. “We tried to go a nice Thai restaurant, but it had a 45 minute wait (pretty unusual for the place) and we were both starving. He turns to me, asks if I’m cool with Taco Bell, and then we sat on the beach eating burritos and talking for hours.”

24. “Our college had a zoo. He was in the zoology program and worked there, so he took me after it was closed. All the animals knew him. He let me stay at each enclosure for as long as I wanted and he could tell me everything about the animals (and plants). It was an awesome experience and so cool to see him doing what he loves.”

25. “He worked at a pet store and he gave me a tour during which he would let me hold snakes, lizards, and his pet ferret who was being housed at the store. Kind of a risky move on his part but I’m crazy about all animals so it was the best day ever.”

26. “I thought I was driving him to and from his wisdom teeth extraction, but turns out he had a date planned before. He picked me up, took me for breakfast, and then took me to an empty parking lot to teach me how to drive stick shift. Afterwards, we did go to his appointment, but it was one of the most unique and sweet first dates I’ve ever been on. Couldn’t really kiss him at the end though, for obvious reasons.”

27. “I went to his place for dinner- he had cooked and I went to sit down. He said, “no! It’s a picnic!!!” And we sat ON the table and had a picnic. After that we built a pretty intense blanket fort and watched scary movies in our fort. Just, so unique and memorable.”

28. “We went to a Yankees game- and almost everything went wrong. I lost my train fair money, our train got canceled, we carpooled with total strangers, almost didn’t have enough money for the tolls and used an annoying amount of change, took the subway all the way to Brooklyn instead of the Bronx, it rained a little bit, we were like 2.5 hours late- but I laughed so hard that day and was with someone I really cared about.”

29. “He took me stargazing for our first date. I drove us per his direction to a place that didn’t have much light pollution. (I have a hard time trusting people to drive me haha.) It got dark and it was beautiful. The sky was very clear and we saw several shooting stars.”

30. “He initially wanted to take me to an art gallery street but realized on the way there that everything was closed that day. After a few moments of panic, he created a plan B to go to the Exploratorium – a building in SF filled with scientific demos and games, usually for kids but that night they were open late, 21+ event. It was like being a kid again.”

31. “We matched on tinder and planned a hiking/picnic date. I had planned on bringing my Chocolate lab to go hiking with us. Once we got there, started hiking, halfway through we stopped to eat our little picnic. He’d packed sandwiches, chips, watermelon, and had even brought dog treats for my lab. It was the most adorable.”

32. “We went to this event for Dia De Los Muertos. It was really beautiful and was taking place at my favorite part of town. The idea to go was mine because he was from out of town. It was nice to play tour guide though because he was full of wonder and it made the date more special because it was all new to him. We walked along the river and took in the lights and music.”

33. “Back in college (NYC), this guy I was really into promised to take me for a ride on his motorcycle. He told me that he’d take me to “Three Bridges,” and at the time, I just assumed it was the name of some bar. He came to pick me up one day just before sunset, and it turned out that he quite literally meant he’d take me across all the main bridges (Brooklyn Bridge, Manhattan Bridge, and Williamsburg Bridge). It was truly an unforgettable date, riding across the river during sunset, with the beautiful New York City skyline in sight.”

34. “The most romantic date I ever had was in the 90’s with a guy I locked eyes with in a pet store while peaking into a lizard aquarium, we rose up on opposite sides staring at each other (just like in the movies). We bonded over our love for reptiles. Soon after we went on a date. I assume we ate dinner, but afterwards we just went to the parking lot at the local college and hung out for hours talking and laughing. The song “A Whole New World” from Disney’s Aladdin came on the radio. He asked me to dance. I was shy and awkward. It was a really nice moment, just slow dancing in the wee hours of the morning without anyone around. I was super smitten.”

35. “Rented a brand new sports car and drove 3 hours to Atlanta Braves game! Then he took me back to his dental practice and cleaned my teeth!”

36. “He took me to a shooting range. Taught me how to shot different guns. The best date I have ever had.”

37. “Met on Craigslist, met in person at Starbucks, He packed a picnic lunch as a surprise: with a Mediterranean flair- olives, bread, wine, cheese, cloth napkins, real utensils, etc. Took me to the tide pools on the CA coast where we ate and drank and looked at sea creatures and enjoyed the sun and sand.”

38. “He brought me to one of those farms that was decorated with events and attractions for the Halloween season. Which was great because I liked him and wanted to test out how he’d react to me clinging onto him due to scariness of the rides.”

39. “We went to the mall and straight into the Lego store. He bought us some Lego packs and we went into the food court and built the while we had an awesome conversation.”

40. “So we decided to meet up and see where the day would take us. We were driving and just stopped at this souvenir store off the main highway. They had canoe day rentals for only like $14, so obviously we did this. On our way to find water, we pass a pizza restaurant in a small town. Stop there and order us a pizza. Soon enough we are on a crystal blue lake canoeing.”

41. “He took me to a light festive and for dinner we found this underground french dip place (10/10, super good) and right next to it was a thrift shop. we spent the night walking around the thrift shop and seeing all the lights on the buildings.”

42. “We met up at his school and walked for hours across town toward mine. We climbed on a jungle gym and talked about our lives, had lunch, went window shopping, and geeked out at gaming stores. It was freezing so he gave me his gloves to wear and said that way I’d have to see him again. Then he tried to finish the date with a high five, but I went in for a hug. It was all really dorky and cute.”

43. “First date was at the science museum of Minnesota, and he was genuinely interested and knowledgeable about the exhibits. We had fun sharing made up ridiculous facts about everything too.”

44. “We met up at this cool oyster bar and sat on the patio chatting until the sunset. He then took me out on his motorcycle! We kissed under a lamp post outside my house.”

45. “He knew I loved Christmas, he knew I loved to drive around and look at the Christmas lights and displays. So he took me to a whole park with a huge lights display. A huge Christmas tree made of lights that changed with the music, and a bunch of other cool little set ups. I was in awe the whole time and so happy, like a kid in a candy shop.”

46. “I met a guy while going through a tech program. While hanging out after class with some friends one day I told him about my blog and my bucket list I had on it. When he finally asked me on a date, he wouldn’t tell me where we were going. It was October, so he took me to a pumpkin patch and then drove around the city for a bit. When it was getting dark, he started driving and wouldn’t tell me where we were going. We finally pulled up to the biggest haunted house near us, which was an item on my bucket list!”

47. “He invited me to his house to play Halo 3. I don’t play games on consoles, so I sucked at it. But (I found out later) he let me kill him a few times to boost my self-esteem. If I remember correctly one involved throwing himself of a cliff to pretend I shot him. It was cute. We shared a kiss and after that I had to go home for dinner.”

48. “We were both into photography, so we took our cameras out into the city and took pictures of random stuff. I guess it wasn’t really very glamorous, but it fit our personalities and gave us something to do together other than eat or watch a movie.”

49. “We purposely got over-the-top dressed up to go to dinner. Turns out, we were both getting sick and it hit us when we got to the restaurant. We took turns running to the bathroom to throw up. We got our food packed up without even taking a bite. He drove me home, we changed in to pajamas, got into bed and watched movies all night.”

50. “We went to the zoo. In the bat cave she was a bit frightened and it was dark so I held her close and guided her through.”

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