Men’s Most Romantic Dates

From planning a surprise road trip with a new love to reigniting the spark after 20 years of marriage, men reveal their most unforgettably romantic moments of all time to help inspire you.

By Dave Singleton

n my recent conversations with men, the two words I heard most frequently while they described the most romantic dates they’d ever experienced were “surprising” and “unforgettable.”

I suppose it’s no shocker that “surprising” would top the list. After all, as much as we’d like to plan out every minute of an unforgettable
I got such a mystical feeling when I showed up at her home to pick her up.
experience, that doesn’t always work, does it? Timing, execution, luck and a little bit of magic must combine in such a way that seldom produces such stunning results… but when they do, look out!

From an impromptu first road trip to Las Vegas to revisiting the site of an iconic date 20 years earlier, read on as these men reveal their best (and most unforgettably romantic) experiences:

“We gambled on a road trip to Las Vegas and won — big time”
“Lisa and I were dating for just a few weeks when I came up with the idea to drive to Las Vegas together,” relates Los Angeles-based Eli, 29. “We’d already gotten comfortable, and after a long week at each of our challenging jobs, we’d often crash on her sofa to watch TV after making dinner together. Maybe we were too comfortable. I could tell we were heading into a kind of ‘Rut Land’ where we’d both sink into boredom. I wanted to head east with Lisa on our first road trip, so I made reservations at a great hotel and restaurant for Saturday night, but otherwise kept our plans loose. On Saturday morning, we took off with a special music playlist I’d created and a basket full of her favorite food and drinks. That night, we joined the crowds in the casino, played the slots, and had a few drinks. Amidst all of this crassness and noise, we were like two kids together, totally in sync and having fun. It felt like it was just the two of us against the world. We ended the evening by making out in front of the Bellagio Hotel’s colored fountains. Needless to say, we avoided Rut Land! I think of this as the most incredibly romantic time we’ve spent together.”

“An awesome night sky filled with shooting stars restored my faith in romance”
“I met a woman at a friend’s July 4th party and we hit it off, but my guard went up immediately,” says New Mexico resident Rico, 47. “I was recently divorced, new in town after moving from Texas, and so freshly wounded from an unpleasant breakup that I’d stopped even thinking about pursuing a new romance. Nothing happened that night, but we kept in touch through emails and a phone call or two over the next two weeks, taking it slow. Then, I asked her to attend an art opening with me in Santa Fe. I got such a mystical feeling when I showed up at her home to pick her up. We went to the art opening, and after an hour, she asked me back to her place so we could talk more privately. So we left, grabbing a bottle of wine on the way, and she led me into her backyard where she lit some torch-like candles. We kicked back on chaise lounges to look at the stars, which flooded the sky. We talked about some constellations we both knew — and then saw three shooting stars. I’d never seen anything like it. We actually felt a moment of awe at nature’s beauty together, which was quite a bonding experience. With her easy grace that night, this woman reminded me that romance can begin again when you least expect it… even when you’re my age and have already been on the darker side of love once or twice. We’ve been seeing each other ever since.”

“She hit a home run by planning a perfect birthday for me at the ballpark”
“My girlfriend, Trish, knew that I loved baseball, so she surprised me for my birthday by taking me to an Orioles game,” says Baltimore native Tony, 34. “It’s my pick for most romantic date because she paid attention to what I liked, and I was used to the
We drank wine, huddled together, and talked for hours.
shoe being on the other foot. For years, I’d been the one to find cool activities that I hoped would appeal to the women I dated. In fact, I was planning a night out for Trish and myself when she sent me an email a week before my birthday with the subject line ‘Batter Up’ and inside, a simple message: ‘Hey handsome, are you game for me to take you to a game?’ Before we left for our date, she presented me with two Orioles t-shirts so we could both wear them that day. When we got there we ordered beers and hot dogs, and she just seemed to enjoy how much I was into everything. That date was much more romantic than anything I could have dreamed up.”

“I rekindled our romance by surprising her with a different kind of anniversary celebration”
“When you’ve been together as long as Linda and I have, it’s hard to pull a rabbit out of your hat to create new relationship magic,” says New Yorker Frank, 49. “She and I had agreed years ago that anniversaries were no big deal. We’d celebrate and do fun things as they arose without showing any great concern toward the actual anniversary of our wedding. We’d gone to a few new restaurants that had recently opened in the city; we’d also taken some great trips in the past couple of years to Greece and London. It wasn’t like we’d stayed at home, but we’d been missing out on the spark. So this past year, as a surprise, I decided to celebrate a different anniversary. On April 19 (which was the 20th anniversary of our first date together), I took her to the Central Park Boathouse — which is where we’d both first realized that we were in love and uttered those three little words two decades earlier. It was a beautiful spring night, just like it was back then. We sat at the same table and ordered red wine again. Words can’t express the look on her face as we sat at the very spot where I’d leaned in to kiss her after the first time we’d said ‘I love you’ to each other. That was the most romantic date of my life, because those memories reignited our spark.”

“Sunset at the beach with a sexy stranger made my summer even hotter”
“The most romantic date I ever had happened during a trip to Provincetown, MA in June,” says Boston resident Alex, 31. “I took the ferry over to visit some friends. One day as I was bicycling to the beach, I stopped for a water break and met a guy named Rob who was also there visiting his friends. We just hit it off big time and ended up biking together for a couple of hours that afternoon. He was from Atlanta. We didn’t want our time together to end, so we both did something atypical. We called our respective friends and begged off our plans for that evening so we could spend it together — just two of us. We agreed to go home, take showers, and meet back up at the beach around sunset. I remember the feeling of anticipation as I waited on the sand for him to appear again, and boy, did he clean up well! We drank wine, huddled together, and talked for hours. Sitting with him there on this beach at the end of Cape Cod, I felt like we were the only two people on Earth. We didn’t end up dating due to the long distance between us, but it’s still the most romantic date I’ve ever had.”

“Our Valentine’s Day date might’ve been late… but it was perfect”
“My most romantic date is unforgettable simply because of the actual date,” said Washington native Jimmy, 36. “It was on February 15 — the day after what the world has come to regard as romance’s biggest night. A few years ago, I’d made Valentine’s Day reservations at one of the best spots in the city. It was a place I knew my girlfriend, Jan, was dying to visit. But that morning, there was a blizzard and we got snowed in. I couldn’t get to Jan (who lived 10 miles away from me) because the roads were terrible. Snow was everywhere. Normally, I’d have loved that sight… but on this romantic holiday, I was so bummed! We talked on the phone, both of us sad about missing our date, and especially because I was supposed to leave for a week-long work trip the very next day. It looked like we were going to miss out on celebrating Valentine’s Day altogether. But luckily, I rearranged my work trip so I could surprise her by spending time together on the 15th. The roads were better, so I went to her house with champagne, flowers, and dinner in hand. We took a walk in the snow outside and kissed under the moon. The snow ended up being pretty romantic after all. We both agreed afterwards that this particular February 15 was the best Valentine’s Day date we’d ever had.”

For the other side of this story, read: Women’s Most Romantic Dates.

Dave Singleton, an award-winning writer and columnist for since 2003, is the author of two books on dating and relationships. Send your dating questions and comments to him at
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