We Scoured the Country for the Most Inventive First Date Ideas Ever

Let’s be honest: Most first dates, those would-be magical encounters laden with anticipation and way too much outfit planning, are completely and utterly…fine.

But every so often, some of us are lucky enough to go on one so special, either through sheer spontaneity or meticulous planning, that even if the relationship doesn’t go beyond than the end of the evening, the memory of it still conjures a smile years down the line. Here are some first dates we’d be more than happy to go on:

Sarah, 37, New York, NY
I went on an awesome epic date in college. We started out recording his campus radio show, picking out music and discussing it (on air!). Then we went to a friend’s art opening, had some food and bubbly and good art talks. By then, the snow had gotten really high and we “borrowed” trays from the campus cafeteria and went sledding for a couple of hours. Once we were exhausted, we went out for hot chocolate and a long walk in the snow. The whole night was awesome. I had a big smile on my face the whole time, like a good rom-com. The relationship didn’t work out for a lot of reasons, but that guy was an excellent date planner.

Julie, 29, Providence, RI
I once had a guy text me every hour on the hour from noon-5 pm on the day of our date. Then he planned the entire date around my answers to questions such as “Chocolate: Milk or Dark?” and “Frisbee or Soccer?” “Vacation: Mountains or Beach?” to which I replied, “Neither, I like cities.” and “Country or rock music?” and “East or West Coast?”

We then went on a series of adventures involving my answers. First stop after dinner was buying dark chocolate at a candy shop, then playing frisbee golf in park. Afterwards we headed to the balcony of the Rhode Island capitol building in downtown Providence and danced to country music playing on his phone. At the end of the night we walked along the east side of the canal that runs through the city.

It was definitely one of the more memorable first dates I’ve ever had. Personally, I felt it was a little too over the top and wasn’t feeling his vibes, so there was no epic second date. But I did wonder hypothetically what he would plan for a first year anniversary date since he set the bar so high from Day One!

Rubina, 33, New York, NY
I was 15 minutes late to my first date with my now-husband because I was watching a “Lost” marathon with my roommate. I was fairly jaded about online dating, and we’d talked briefly on OKCupid before deciding to meet at a vegetarian bistro. We had a great conversation over martinis and veggie meatloaf. Afterwards we went to a dive bar, where we cuddled on the same side of a booth while sipping Jack and Cokes. I asked him, “What are you looking for in a relationship?” He said, “I want to eventually get married and have children… and I could see myself doing that with you.” He told me he loved me the same night. Eight years later, we’re living in Astoria, Queens with our toddler daughter and a Pekingese we adopted. Sometimes I think about how I was 15 minutes late to meet the most important person in my life.

Amelia, 34, Washington, D.C.
Backpacking solo after college, I found myself on a bus from coastal Slovenia into Ljubljana. I needed a hostel recommendation and saw a guy reading a guidebook in English. He was a handsome and friendly British journalist at the end of his holiday, flying back to London early the next morning. He didn’t have a reservation either, so when we arrived at the hostel, the host assumed we wanted a room together. I didn’t object to this arrangement – and neither did he.

We spent the day and evening walking around the beautiful city seeing the sights, talking about music, politics and travel. We explored the city’s medieval castle. We got drinks and dinner at a swanky bar overlooking the river. We met some interesting locals and kept exploring the city late into the night, just talking and talking. It was super romantic but he was almost frustratingly gentlemanly. When he finally kissed me I told him that an American boy would’ve had me in bed hours ago. He apologized very British-ly, and then he made it up to me until dawn.

Alyssa, 36, New York, NY
One of my best first dates was with a guy I met at a book party on a work trip in San Francisco. The next time I came through town, we drove down the coast and climbed to the top of Tree 9 (a famous, 150 foot redwood), visited his buddy at the Kombucha factory and got “seconds” cookies at the Pacific Cookie warehouse in Santa Cruz.

Carmen, 31, Austin, TX
I’d just gotten a huge promotion a few hours before a first date. I mentioned this when he texted to confirm the time because I couldn’t contain my excitement. An hour later, he texted again, requesting I bring two specific sets of clothes. We started out paddle boarding down the river (something I love), then changed outfits and went to dinner at my favorite restaurant in town, where I didn’t have to order anything because all the things I loved were automatically brought out to us. After that, we went two-stepping – and the band leader ended one of the songs singing congratulations to me on the promotion! Turned out, my date had done some quick online research to tailor the perfect, over-the-top evening after learning about my good news. All the more impressive since he later confessed that his original plan was to just go catch a movie! Our relationship eventually crashed and burned, but I still smile when thinking about that night.

Rachel, 38, New York, NY
After two years of rejecting a friend’s overtures, I realized I was finally ready for more. I asked him to come over under the terribly unromantic guise of putting together furniture. Of course, my terror at revealing my feelings caused me to become, well, psycho. Instead of professing my feelings, I nervously criticized his furniture assembly technique. So he left. I called him a few hours later and blurted out that I was sorry and wanted to date him. He replied, “Shouldn’t we talk about this in person?” And so, he came back to my place, and a date that began with furniture assembly and yelling was transformed by him asking me out for dinner and jazz, immediately followed by a weekend in the Hamptons. The whole experience ended up being a lot more over-the-top than spending the night with an Allen wrench!

Tara, 44, Boston, MA
I was set up with a woman and connected over texts over our love of the movie “Groundhog Day,” since the holiday was coming up. She asked if she could pick me up for our dinner date, so that only one of us would have to drive. When she arrived, she announced we were driving more than seven hours to Punxutawney, PA for the annual Groundhog Day celebration! I should’ve been completely freaked out, but I just went with it,. We arrived in the middle of the night, just in time for the sunrise celebration.

Kathryn, 33, New York, NY
The day of the date, he sent me a text of a video of an older gentleman friend riding his bike and wearing this amazing bright blue vintage “Ghostbusters” shirt. Random, I know. He then texted me to say don’t worry about the bathing suit he originally asked me to bring— a storm was coming so he changed plans. I replied, “No problem. And tell that guy I want his shirt!”

The date itself was great. We went to a concert, then for drinks and dinner and then a friend’s party. It was hot, so we laughed the whole time about how sweaty we were. Literally sweat was dripping down my face and back the entire time. It wasn’t cute. But nothing tequila couldn’t solve! I didn’t hear from my date for most of the next day. Then at 5 pm, a messenger brought a package to my office: a brown paper package smelling of sandalwood and lavender. I unwrapped it to find a vintage postcard from Morocco with two camels on it with the note, “Last night we were like camels in the desert…searching for an oasis of Tequila! Congratulations, we won the prize for world’s sweatiest date.” Underneath the postcard was the “Ghostbusters” tee shirt, freshly washed and pressed, just for me. I totally melted.

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