25 People Tell Us About The Most Romantic Dates They’ve Ever Been On

25 People Tell Us About The Most Romantic Dates They’ve Ever Been On
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Let’s be honest: When it comes to dating, the potential for bad or boring is huge. Even when you bring your A-game or have a great connection, not every date can be The Best Date Ever. The most romantic among us still has to occasionally settle for the staples: dinner and a movie or a quiet night in—even if you do have a million romantic date ideas. And that’s not counting all those dates that are just devoted to the 21 “Where are you from/What do you do/Do you have any hobbies” first date interview. It’s a part of life!

The statistical probability of having an average date is what makes those precious “perfect” date moments so extraordinary. Whether it’s memorable due to perfect planning, thoughtfulness, or just pure connection, the perfect date can stick in your mind for years to come.

StyleCaster reached out to people to hear some of their favorite date stories, and they definitely delivered. From pet adoptions to road trips to a little role playing, these GOAT dates are as varied as the people who shared them. Enjoy their stories, and maybe incorporate some of them the next time you’re looking for a way to make an occasion extra special.

Alaina, 26 — Animal Shelter Date

“One night, my partner asked me if I wanted to go on a date to the animal shelter. We hadn’t planned this in advance. We’d just moved into our first apartment together earlier that week after several years of dating. We looked it up, and the animal shelter in our new city was open. So we went! We fell in love with a bonded pair of two-year-old cats. We talked about it after we left and decided we wanted to adopt them, so we went back later that week to pick them up. We have had Blue and Gansey for almost four years now and that was one of my favorite dates because it brought us our cats, who are seriously so loved.”

Cheyenne, 28 — Camping Mishap Turned Romance

“We had plans to go camping for Fourth of July a few years ago because both of us were dying to get away from the city and just be in the outdoors without anyone else around. We had planned it for weeks and were so excited, but the day before he unexpectedly got called into work and his only options were to A: show up or B: be fired. We were sooo bummed that our weeks of planning were just thrown out the window because of some error on his boss’s end. But at that point we didn’t really have a choice so we chalked it up to an ‘it is what it is’ situation and just went about our week: him going off to work on the Fourth and me at home throwing a pity party. When he asked me to come over later that day I was hesitant because I was pretty bummed, and since our relationship was fairly new, I didn’t want him to be able to see that emotion in person. When I got to his house, he brought me to his deck where he surprised me with his city version of camping under the stars. He put up a tent, brought out an air mattress and made it super cozy inside, then added a finishing touch of sunflowers (my favorite!) in and around the tent. He even brought out his camping grill and had an entire “campfire dinner” planned – of course there was beer too!”

Kathryn, 26 — Snow-Covered Love

“When my now-husband and I first started dating, we went to college in the very cold, yet beautifully snowy Upper Peninsula of Michigan. Our most memorable date was a beautiful nighttime walk on a trail that wound through a snow-covered forest. The snow was falling in big, puffy flakes and sticking to the each and every branch of the trees. Every time there was a break in the trees, we could look up and see millions of stars. We just walked and talked for an hour or two as we trudged through the snow together holding hands. You can’t put a price tag on something as beautiful as that! That date happened when we were 18. We were just kids, and yet it was the start of something truly magical as we have been happily married for 4 years now! It felt like something pulled from the pages of a romance novel.”

Ariel, 24 — Peaceful Nature Moment

“One of my most memorable “dates” (if you can call it one) was with my now-boyfriend, who is the wild adventurer type and always wants to try new outdoor activities. When we were in Arizona, we found a dirt road in the mountains and decided to see where it lead. He took me on his motorcycle, and we went up the mountain, through a river and between trees until we found a beautiful clearing with no other souls around. It was by the river on a lovely sunny day, so we laid down in the sun and listened to the water flow and watched birds up ahead. It was a perfectly peaceful moment — nothing else mattered in the world. We shared childhood memories, observed the outdoors and talked about the simple joy of life, like this moment. After sunbathing here for a long time and maybe falling asleep, we went to a high rock and meditated, soaking up more sun and feeling nature’s energy sink in. There was no money involved in this date and it was the best one I’ve ever had!”

Nick, 27 — Candles & Conversation

“We drove about 15 minutes outside of the city through trees and fields to get to a restaurant that used to be a farm house. The table we got was in the back and very private. We had the most amazing candle lit dinner. There was good conversation the whole time, even on the car ride home. We took a minute to stare at the moon and the stars and that was it.”

Maddy, 24 — Fireflies Fluttering

“One time in high school my then-boyfriend took me to this huge field in the middle of nowhere that lit up with a WILD amount of fireflies at night. He knew I liked seeing one or two fireflies so the thoughtfulness and how beautiful it was was amazing!”

Amy, 26 — Christmas Lights Abound

“When my partner and I first started dating (early December), we spent one night going to get Starbucks hot chocolate and driving around looking at all the Christmas lights and talking. It’s still one of my favorite dates we’ve ever been on.”

Stephen, 25 — It’s the Little Things

“Very recently, a girl and I met up at the National Harbor in Maryland. It was our first date but we just said let’s wing it. We got Colombian food and walked around the pier before going to a wine paint bar where we could drink while taking a Bob Ross-like painting class. Afterwards I drove her back to her car and she had a deflated tire. I taught her how to pump her tires but she had a puncture anyway. She was stuck so she came to my place, put on some of my sweats and we just had a nice night of smoking weed and held hands until we fell asleep.”

Liam, 25 — Desserts-Only Picnic

“I took my high school girlfriend on a candlelit picnic to this place in Austin called Mt. Bonnell. It’s a super scenic lookout. Surprisingly there was no one else there. We had gone out to dinner before so it was more of a dessert picnic (hot chocolate in a thermos and brownies). I think it helped the romance of it because the whole date was a surprise for her and she hadn’t been there before.”

Rebecca, 25 — Scavenger Hunt

“I brought my high school boyfriend horseback riding for our 2nd year anniversary and then we got back to my house and I had planned a scavenger hunt that ended in a “picnic” in my basement with Chinese food.”

Nicole, 43 — Cooking Competition

“We each made a burger at home and had a fun inexpensive competition. Basically we went shopping together and grilled at my place. It was super fun and super inexpensive and I won too (I put stuffed blue cheese olives in my burger)!”

Lindsey, 25 — Keeping Up with the Interests

“We went to a fancy sushi restaurant and then post-gamed at his place with a quick chat about data analytics and a lot of Keeping Up with the Kardashians. Not everyone’s idea of romance, but he’d taken care to incorporate so many of my favorite things into our first date together that my panties basically hit the floor the moment KUWTK ended. (Not before. Gotta finish the episode.)”

Nick, 27 — Furniture Store

“One time I went on a date at a furniture store. We just sat and laid on all kinds of different furniture and had great memories and comfy conversation the whole time.”

Janet, 24 — Bar Hopping & Museum Kissing

“I once went on a first date where we went to three bars in one night and kissed on the steps of the Brooklyn museum. It felt like a dream — not particularly because of the activities we did but just because there was a really great connection between us.”

Alaina, 26 — Do I Know You?

“My fiancee and I decided to pretend we were going on a first date a couple of years ago. So we pretended we’d never met and did things like ask getting-to-know-you questions, hold the door open for each other, and try to see when the best time was for a “first” kiss. It was really different and sweet.”

Lia, 24 — Steal Kisses, Not Art

“We went to an art museum and stole kisses in the rooms that were empty and then had dinner in a restaurant that overlooked the city.”

Cathy, 53 — Gettin’ Fancy

“Dinner on Valentines Day at a local restaurant that was ‘too swanky’ for my parents to take us to as children. It was special because it was probably the first *NICE* restaurant I’d been to and also that we had both been too busy to make plans and he pulled it off at the last minute against all odds.”

Maddy, 24 — Permanent Love

I got matching tattoos with a dude from a dating app as a first date (both of us already have several tattoos so it was no big deal to us).”

Sherry, 55 — Italy Isn’t So Far After All

“My beau and I are always taking about how much we’d love to go to Italy together to ride a Vespa and drift through Venice on a gondola. One time we were going out to dinner at a restaurant in Jack London Square, in Oakland. We had a wonderful dinner together and then hopped back on his motorcycle to head home. He yelled back to me and asked if I would be okay if we stopped by Lake Merritt to see the lights at night. Sure thing.  He pointed to something on the lake and said, “Hey, what’s that … let’s go check it out.” When we got closer, I saw that it was a beautiful, gleaming GONDOLA! Ian said, “Shall we go for a ride? “ I didn’t know it at the time, but there are actual Italian gondolas that people can rent out and ride around Lake Merritt — in Oakland! Ian had reserved the gondola for us and he unpacked his bag, which had a bottle of wine and some chocolate truffles! Our gondola driver sang Italian love songs as we drifted under the moonlight sipping wine and laughing. Holy Toledo, was that a romantic and beautiful evening! The love was multi-layered: that he had planned a surprise, that he had discovered a way to bring Italy to us, that he brought the wine and chocolates, that he was so charming and handsome all night, etc!”

Nicole, 28 — Twinkling Lights Do It Every Time

“There was a restaurant in Wilmington, NC that is now closed where each table had its own private balcony overlooking the sound. I went there on a date one evening after dark, and there are a lot of twinkling lights in it was just a beautiful place.”

Joshua, 22 — I Choose You, Pikachu

“I brought over Pokemon games and we played and got drunk off cheap drug store wine.”

Sarah, 24 — This Club Is Jumpin’

“One time I told my boyfriend we were going on a date but didn’t tell him where. I drove for about 30 minutes and he tried to figure out where we were going the entire time. We ate dinner and then went to a trampoline park. Somehow we were the only ones in the entire place, which was so great.”

Toby Hopper, 67 — Just Don’t Look Down

The night my husband proposed to me. It was in St. Louis Missouri and the top floor of a hotel was a revolving restaurant. We were dressed up, the meal was amazing, and when he asked me to marry him it seemed like my life was complete!”

Jeannie, 25 — Watch Out Below

“One of the best dates I’ve been on was hitting golf balls off a mountain (we had hung out before so safety wasn’t an immediate issue). We drove up and he didn’t tell me what we were doing, just to dress warmly. When he told me what we were doing, it sounded pretty stupid. However, once we started doing it, I found it very therapeutic. There was no concern for what would happen once we left, just us laughing and talking while channeling some rage. I also got some ‘lessons,’ and who is going to complain about that?”

Shanon, 42 — Music to My Ears

“I was dating a music professor. He planned our last date before I was scheduled for surgery and didn’t tell me what we were doing. He picked me up that evening and drove me to the waterfront. We walked by the piers and sat on a bench overlooking the water while he told me how he felt about me in great detail. He had never opened up to me like that before, though I’d already made it clear I was smitten. He drove me to a little jazz club and sat me down at a table. He ordered my favorite drink from the bar, a French Martini, and told me to order anything I wanted from the menu. Then, he stood and said he needed to do something. He walked over to the band that was performing. Turns out he’d arranged to play for me. He’s a trombonist with his own band. He said he knew I was disappointed I wouldn’t be able to attend any of his upcoming shows. I’d never seen him play live. He chose to perform a Billie Holiday song. At one point, he sat down at our table and played his trombone beside me. I tried to keep it together, but I cried like a baby. The entire date was so thoughtful and romantic.”


A version of this article was published in 2018.