What's the Best Date You've Ever Been On?

Prince Charming does exist and we have best date stories to prove it.
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What’s the Best Date You’ve Ever Been On?

Prince Charming does exist and we have best date stories to prove it.

-Brittany Roshelle Davis

 couple in a carriage

Ask any woman and she’ll quickly tell you her worst date story ever. We’ve heard about them, or had lived through them. You know, the time when the guy turned out to be a psycho- he was still texting you months after your one and only date. Oh yeah, then there’s the guy who stood you up. And let’s not forget those happy moments when your date got so plastered he didn’t remember his own name, or he showed up so stoned, he was on another planet. These are just mild versions of the many, many sad date stories floating around out there. Those stories are the ones that keep us up late at night, repressing memories and swearing not to date for a long, long while.

 Read Tough Love’s Steve Ward: “Are You Dating or ‘Hanging Out?’ “

But what about the one or several dates you’ve been on where a guy just swept you off your feet? When he managed to say everything right and do everything right? Those stories keep us Bettys warm on a cold winter night. Those are the stories that make us decide to chuck the ice cream and bad movies and try again. Here’s a round up of best date memories that we want you to remember the next time He Who Must Not Be Named ruins your date night.

It was the second date I had with a guy I’d met on Valentine’s Day. He took me to the local mountains for a picnic at a very beautiful spot with big rocks and a sparkling stream. We spent the day together drinking a bottle of Cabernet and eating sandwiches. At the end of the day, we climbed up onto one of the big rocks and watched the sunset together. At that point, he invited me to go on a backpack trip to Tahiti, New Zealand and Fiji, where we spent two months adventuring and getting to know each other. We have been together ever since.


I met a great guy and after we had dinner together he offered to take me skydiving the following weekend. Not only was it exciting but it was extravagant. He paid for the tandem dive and also bought a video of the experience for me! This meant that a videographer jumped out of the plane just before I did and caught up with me IN THE AIR to film me as I flew through the air. It was an awesome experience and although the relationship didn’t last, the memories of that skydive did!


It’s been rough dating in San Francisco. I don’t know if it’s the dating pool, the weather or my standards, but I finally met someone over Labor Day weekend in Los Angeles. We were standing in a ridiculously long line to enter a bar and started chatting. I didn’t think much of it at the time, especially since he lives in LA and I live in San Francisco. When I returned to the Bay Area, he insisted that I let him take me out on a date in my home city. We started the date with a breakfast in Union Square, played tennis for a couple of hours and then went for a beautiful hike in Redwood City. It felt so natural and we were instantly comfortable with each other. He then took me to an amazing restaurant for dinner and we just hit it off. Since our first date, we talk on the phone every day and he plans to fly up next week. I’m looking forward to it and have a good feeling about this one!


I was 19 and while my date and I didn’t have money, we had his Jeep, a digital camera, and miles of gorgeous autumn countryside. We drove the backroads and through a state park and just stopped whenever we saw something interesting and conducted a mini amateur photo shoot. The guy didn’t last much beyond the season but the spontaneity and creativity of that date still makes it my best date ever.


My date took me to a standard, first date restaurant, The Chart House. To be honest, this was the umpteenth time someone had taken me there and I was bummed on the lack of creativity. Apparently my lack of enthusiasm showed and the date was NOT going well. After we finished eating, my date was over me and figured if I was going to be so blasé, he would go somewhere HE wanted to go and we left our expensive restaurant and he took me to a bar complete with a singing piano player who had missing teeth. We sat at the bar that surrounded the piano. We requested song after song and laughed hysterically along with the piano player. Now THIS was the creativity I was looking for! Later, he and I got married.


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