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20 Exciting and Enjoyable First Dates People Will Always Remember

First dates hold a special place in our hearts as they spark excitement and fond memories. Recalling those enjoyable experiences, especially if they lead to subsequent dates, brings an irreplaceable charm to the first encounter. How have your first dates played out? Are you eager to delve into the world of first-date adventures?

Study Sessions

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One Redditor shared, “The one with my wife. It was supposed to be a group study session in a Mexican restaurant. We were the only two to show up. We decided to make it a date. I told her I was in love with her that night. Twenty-one years together Friday.”

Keep It Low-Key

Simple Conversations: Happy couple talking and sitting together.
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This Redditor said, “The first date with my future wife was perfect and tremendously low-key.  Got a nice dinner at a place where you could draw on the tablecloth with crayons and ended up covering the table in goofy doodles and cartoons together.  Then I took her to my favorite park in the world and wandered around chatting until it got dark, then we went back to my place to watch a terrible movie and make out in a sea of pillows.”

Pay It Forward

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A user recalled, “I went on a date at an Italian restaurant with a pretty girl.  We sat at the bar and had a round before we ate dinner.  I bought the drinks, and when I pulled out my wallet to pay for dinner, she said, “You got the drinks. I’m going to get dinner.” I am married to that pretty girl now.”

At The Prom

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This Redditor shared, “My first date was at Prom. I’m homeschooled, so I didn’t know anyone, so I got set up by a friend. I was very nervous on the way to pick up my blind date, partly because it was my first date and partly because I didn’t know if I’d like the girl or not. We talked while at the prom (we had many common interests), ate, and danced. Had a really great time, and then we went to the after prom at her high school. We got along great, played games, and held conversations all night. We hung out until 5 in the morning.”

Musical Interests

Teaching man teaching woman to play guitar
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This user stated, “My best first date was when a guy took me to 3 music stores with one requirement. I had to find a CD at each one (which he bought!). He said nowadays, with digital music being so popular, no one ever goes to music stores anymore, and he wanted to change that. Later we swapped albums. It was so fun, creative, and a total surprise!  Afterward, we got candy and watched Dr. Strangelove at my place.”

The One

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One Redditor reminisced, “I had one perfect male friend in high school. The kind of boy who actually listened to your stupid teenage b****t about your c****y boyfriend and your pointless insecurities, the kind of boy you never take seriously as boyfriend material Years later, when he came home from Basic Training, his life was in shambles. I stepped in to repay the support he gave me through the screwiest time of my teenage life. Our first official date: Phantom of the Opera. Full Army Uniform. Fancy dinner. Six years later: we’re happily married and starting our own family.”


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A commenter said, “We met at his place since he lived close to the restaurant we were supposed to go to. It was his birthday, so I brought a bottle of wine. We sat on the couch and talked and talked and talked, and when I looked up, it was almost 10 pm, and we had missed our dinner reservation by hours. We made a late dinner together and had our first kiss by the stove as we cooked. We shared the wine, talking and laughing the whole time. I didn’t leave until nearly 2 am and just floated home.”

Late For A Date

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A user stated, “We decided to meet at a coffee shop. He was running close to an hour late (traffic). I’m pissed- slurping down espresso after espresso out of stubborn refusal to admit defeat, I decided not to go home. All of sudden, here he comes, sucking all the color out of the place and tucking in his shirt, and falling all over himself apologizing. We talk until the coffee shop closes. So we go to a bar. Talk until the bar closes. We’re walking to our cars, and he grabs me by the face, says, “I’m not ready for this night to be over.”

Plane Ride Away

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A Redditor recalled, “My best (and hopefully my last) first date was 21 hours long. I bought plane tickets to visit a guy I’d met twice when he came into work; I’d known him in person for maybe 2 hours. He asked me out, and I turned him down (just getting out of an unhealthy relationship). A month later, I’d been thinking about him every day since I turned him down. I tracked him down on Facebook. After a week and a half of texting/phone calls, he invited me to visit over the weekend. I had to work all day, so I took a late flight and had to fly back the next day… We got to his place, and it was so late there was nothing to do but go to bed. We talked all night, held each other, made out, and slept. Sunday, we went to church, assembled a coffee table in his living room, and he put me on a plane back home. I knew I was in love with him the second I stepped on the plane.”


Hammock Swinging woman laying on hammock reading
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A user said, “Went to see some random movie, then roamed over to the local Borders. Spent 45 minutes to an hour in there browsing books and talking about what books we liked and disliked. I’ve known this girl for 15 years, and we decided to try it. This was over 3 years ago. We are still together. Since then, we try to go to a bookstore at least once a month together. Yes, I’m a nerd. Yes, she is a nerd.”

Halloween Parties

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A top-liked comment said, “I met my now fiancée at a fraternity Halloween party. After talking for some time, I get the nerve to ask her to my fraternity’s formal, and she agrees. At some point later, her friends leave with her car. We wander back to my place after talking for hours and lie in my bed. The next 6 hours are us talking, laughing, smiling, and holding hands. We discovered how much we had in common and then went to sleep. It would be months before we’d go on an official first date, but that night I knew she was the one.”

True Love

a couple on the couch looking shocked while watching a show.
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This Redditor said, “My absolute favorite first date was grabbing Chinese takeout and watching The Princess Bride. Nothing like having a girl associate you with True Love!”

Roam Around

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This user said, “My best date had to be with my current boyfriend. We had been friends for about two years and decided to go out one day. We went to this coffee shop I had heard of. We got our drinks and sat and talked. Got hungry and decided to get some food. Most of the day was spent walking around and talking, but at the end of the night, we ended up in the hot tub at a house I was watching. He turned and asked, “Can I try something?” he went in for the kiss, and we’ve been dating for almost a year now. It was a simple date, but I had a lot of fun, and I got to see him in a different way.”

Take A Hike

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One Redditor mentioned, “I had a pretty spectacular one just a week and a half ago. I met this woman for the first time, and after a coffee at Starbucks, we went on a hike on a mountain in central Connecticut. The view was amazing, the hike was long and refreshing, and the company was awesome. The view was great, as autumn in New England often is. Everything clicked, and after the hike, we went to a fairly nice restaurant, and both got awesome steaks.”

Pen Pals

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This user recalled, “Went to China to meet my pen pal, and we had dinner on Chinese New Year at a riverside restaurant. Just before midnight, the biggest, most spectacular fireworks show I have ever seen started above the river right next to us. Perfect night.”

Undeniable Chemistry

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One Redditor shared, “The one with my fiance. I invited him out for my birthday, and we got each other drunk, danced, and groped the night away. We had known each other for a long time already via work but were too wussy to do anything about our feelings for each other.”


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This Redditor commented, “My best first date was with my current boyfriend. We went to the local art museum near our University, and then we went paddle boating at the nearby pond. We finished off with a really cute dinner at the restaurant on the edge of the pond that we paddle-boated to. It was a blast! I had so much fun. We’ve been together 6 years, so it seemed to have worked out well for him.”

Long Drives

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A user shared, “I have only had one first date, and it was with the girl I am engaged to, so I guess that makes it the greatest. We went to an Italian restaurant a few towns over from our college. After dinner, we went back to school, and I asked her if she wanted to do something, and she said we should just go for a drive for a while. I grew up in the area, so I knew of many ways to make a drive that took forever, which I fully utilized. We ended up going by my old middle/high school and where I worked, and a bunch of other places, which I pointed out to her, and she was genuinely interested. Then we eventually, after about 2 hours of driving, ended up back at school. She returned to my apartment with me, and we watched some tv.”

Getting Sworn In

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A Redditor said, “When I got sworn in for the bar, I met a girl in line at a bagel stand who was also getting sworn in. She was a stunner– incredible figure, exotic features, Albanian accent. In a rare moment of suaveness, I persuaded her to grab dinner and drinks to celebrate our new status as lawyers.  I definitely wanted to kiss her, but I wasn’t sure how. No need; she took the initiative.”

Coffee & Conversation

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Finally, a Redditor shared, “Recently, I met a lovely young woman while working security for a Rocky Horror show and got her number, then proceeded to set a coffee date. She showed up on time, and we proceeded to have an amazing three-hour conversation and discovered we had all kinds of stuff in common.”

Source: Reddit

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