13 Men Share The Most Romantic Date They've Ever Planned For A Woman

Steal these adorable date ideas for yourself.

Last updated on Oct 18, 2023

Man and woman having a romantic date Stokpic | Pexels / Muenz | Getty Images / siam vector | SiamVector 's Images / Jacob Lund | Canva

All too often, date nights begin rather unremarkable.

"What do you want to do?"

"I don't know, what do you want to do?"

Obviously, the moment is lost when it's marked with indecision and awkward silence. But sometimes, whether by circumstance or elaborate planning, guys really do get it right.

We asked what men think about planning a romantic evening and any advice they had to offer when it comes to romantic date ideas. Let's just say, these men know how to treat a woman to a magical evening.


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Here 13 men share the most romantic date they've ever planned for a woman:

1. We shared our first kiss in a museum

"Our first kiss ended up romantic, even if it didn't start that way. I wanted to kiss her and tried to while shopping at Target; she said she wanted it somewhere romantic. Flash forward a few hours after driving around DC at night and talking about every topic imaginable. We got to a dead end in the road after apparently taking a wrong turn. I looked up and noticed that we'd arrived at the Newseum's Berlin Wall section, so we got out. I went in for the kiss (and it worked!). After making out for a few moments we apparently attracted the attention of the guards who shooed us away. So, our first kiss was by the Berlin Wall with guards flashing their lights at us and telling us to go away." — James Hills


2. We watched the sunset over the hillside after a wine-tasting

"Going wine tasting until we're buzzed and silly, buying her a bottle of her favorite, dinner at her favorite place, watching the sunset on a hillside. Then a walk in the twilight and back to her place to get drunk on everything we bought."

3. My car broke down, but it gave me an excuse to call her again

"Our first date was a never-ending date that could have gone completely wrong at any juncture but was also one of the most romantic. I wanted to take her to a restaurant but didn't get reservations, and after walking through DC for about two-thirds of a mile, we found that it was closed for a holiday party. I took her to a Vietnamese restaurant and we were lost in each other only to look up and realize that the restaurant was empty and we were surrounded by a bunch of tired-looking Vietnamese people waiting for me to pay the bill and leave.

We then walked down the street to a Cosi for s'mores and pretty much repeated the pattern, but now it was a hipster guy with a man bun that wanted us to leave! We got back to my car and discovered that I left the light on and the battery was dead, so we sprinted to the Metro station to catch the last train to Alexandria where her car was parked. Luckily, we made it, she gave me a ride home, and then I had an excuse to call her the next morning to get my car fixed." — James Hills

4. I proposed to her on her birthday on a "birthday" cake

"This was the night I proposed to my wife. It was her birthday and I had planned on taking her to a cozy B&B for her 'birthday date'. I knew I wanted to propose, but I didn't want it to be the standard run-of-the-mill moment. I had a massive 2-tier heart-shaped cake, iced in lavender and ivory, made for her birthday. Instead of 'Happy Birthday,' it read 'Will You Marry Me?' I lugged the cake into the room without her knowing what it was, set up for a private picnic, and lit candles. We had the picnic basket left at our door, ate and drank, and laughed for what seemed like hours.


Then, it was time. I asked her if she wanted to blow out the candles on her birthday cake and she told me to hold off because she was too full from dinner. I've never asked a grown woman so many times if she wanted cake as much as I did that night! After a couple of hours, she finally agreed and I lit sparkler candles atop her cake and killed the lights. She had to stand on her tiptoes to see the top of the cake, but when she did, she looked over and found me — a trembling and ugly crying mess — on one knee with her ring in my hand. I have never seen her look more radiant — the intermittent glow of sparkler flames across her face, as she said yes." — Josh Ortiz

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5. We ventured on San Francisco's most beautiful walk

"My favorite is one that I've created (that my wife loves) called 'The Marina Date Walk: Taking the Work Out of the Date.' If you're unfamiliar with San Francisco, this walk starts in the scenic Presidio, then heads up the Lyon Steps (the top of the Lyon Steps has one of the best views in the city), then heads down Billionaire's Row, back toward the Marina for local artisanal ice cream at Smitten, followed by craft cocktails at The Dorian. The date has a combo of everything, a little exercise, gorgeous views, stunning landscapes, and a couple of treats to reward yourself."

6. We got lost in each other while staying in a cabin in the woods

"A 1950s cabin deep in the woods overlooking a river, fireplace crackling and a hot tub under the gently falling snow."


7. I proposed in front of the Pyramids

"I schemed a proposal in front of the Great Pyramids at Giza. I had been planning the proposal for over a year. On New Year's Eve, I promised her it would be a great year. We planned a trip to her bucket-list dream destination: Egypt. We woke up in Cairo on the first day of our week-long trip. I hired a black car that literally drove us right up to the Pyramids of Giza.

We explored and around the Great Pyramid, through the Valley of the Kings, and stopped at an overlook to admire the scenery. Right outside the third pyramid, I told her how much I loved her and how I wanted to continue to travel the world with her forever. And then got down on one knee. We spent the rest of the day exploring, and had an amazing champagne dinner to celebrate!"

8. We checked off every item on her bucket list

"I asked her the 10 things she would like to do if she had only one day to do them, and that they had to be within 10 miles of her house. And we did all 10. What were the items on her list? She wanted to walk on the beach. She wanted to watch the sunrise over the city. She wanted to watch the sunset from the mountains. She wanted to be intimate in a public place. She wanted to eat her favorite meal at her favorite restaurant (sushi). She wanted to sing on a stage (we sang karaoke). She wanted to pet every animal at the zoo."

9. We took a hot air balloon ride

"I am married to the love of my life. We met when we were sixteen and became a couple in our early 40s. As far as the most romantic date I ever planned, it involved hot air ballooning. I booked the trip, dinner, and a B&B. On Friday night after work, we drove north through San Francisco over the Golden Gate Bridge. I hadn't told her anything about what we were doing or where we were going. She actually guessed, because there was no logical reason for her to get up before first light on a Saturday morning. It was romantic to me, and really both of us, because I enjoyed the anticipation of her delight and the surprise."


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10. We canoodled all over town

"I picked her up and took her to Georgetown (in the DC area), where we walked around and went to the waterfront. We grazed and had drinks. Restaurant hopped. Pushed the hair out of her face and told her she was beautiful all day long. Went to a few different restaurants. Then, mid-afternoon, I revealed I had a suite booked at a nearby hotel, and woke up to coffee in bed the next morning."

11. We were in a long-distance relationship and I showed up at her door unexpectedly

"I'm not a big romantic gestures guy, but sometimes lightning strikes. We were attempting a long-distance relationship (about 915 miles) and even with the most mature and reasonable people, it's a struggle. And we were both kind of in our first 'this might be the real thing' relationship, so reasonable followed mature right out the back door when loneliness came knocking. I called her at 7:30 on Friday and began talking to her about how it wasn't working out and she should probably start seeing someone else. Ten seconds later, she heard a knock at her door and it was me! One bouquet of flowers and one longboard (she lived near the beach) later, and it was on. We had dinner reservations and we made it to them a fashionable 15 minutes late."


12. We ate dinner above the clouds — literally

"It was just a dinner at a pop-up of a fancy restaurant. We'd been to many of them previously and on the street level it was damp and cloudy, so, not awesome at all. As we ate our dinner, the clouds started to move around and because of our position on the 80th floor of the AON Building in Chicago, we looked up and noticed that we were now above the cloud line with the tops of other buildings around us poking through. Between this and the unexpectedly good food from Le Cirque, it was a fun romantic evening that created once-in-a-lifetime memories. After all, how often can you share a dinner with someone you love AND such an incredibly unique view?" — James Hills

13. I planned a week's worth of fun activities

"I've done everything from a simple pizza picnic at home on the floor, to an elaborate week in California where every morning for a full week when my wife woke up I would say, 'Today, we're going to [insert activity here]!' It felt super spontaneous and exciting but was incredibly elaborately planned and orchestrated. Wine region, camping in state parks, a sunset harbor tour — it puts regular dates to shame!"

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Aly Walansky is a NY-based lifestyle writer. Her work appears in dozens of digital and print publications regularly.