Cute Dating Stories

Cute Date Stories

Cute date stories can take just about any form, but the cutest date stories to me tend to involve humor on some level. I’m not talking about mean-spirited humor or humor at someones expense: I’m just talking about a date which both singles can laugh about it. Both of the next couple of dating stories fit that bill.

We asked a while back for some submissions and I thought both of these would fit perfectly in a “cute date stories” segment. So here is a dating story apiece from Tess and Mary.

Best of Show – Cute Date Stories

When Blake and I made plans for a first date, we couldn’t do it like normal folks. We had had a breezy Internet courtship, so in chat one day, he gave me the choice of a traditional date on a Friday night or a trip to a dog show on a Saturday evening and night. It seems his aunt, who had practically raised Blake, was showing her prized dogs: Penelope and Ulysses. Because I prefer out-of-the-ordinary, I (of course) chose the dog show.

So we get to the dog show and Aunt Brenda decides we are there as her gophers. Brenda is convinced that Ulysses’ “go over” will be a disaster, because Brenda didn’t bring the right brushes. She doesn’t have time to make a trip, so she dispatched the two of us to her house 25 minutes away. We get back just in time for a good grooming, but now Penelope is “nervous”. Brenda asks Blake to “calm Penelope down” while she takes care of Ulysses.

What made this so funny was that Blake had already described this picture to a tee – he had warned me beforehand what we were in for – so the two of us spent the rest of the dog show exchanging smiles and knowing glances, which was a great way to spent the first phase of a first date. When we left the dog show, it seemed like Blake and I had a bond, and the two of us certainly had plenty to talk about the rest of the night.

The post-show date was pretty conventional stuff, but we kept dating and now we have a great story about our first date.


Are Your Amused? – Cute Date Stories

Bill and I had gone on two dates and I still wasn’t sure. First of all, Bill is tall with a great smile and he’s brilliant, so there were reasons for me to stay around to the third date. But there was a reserve in Bill that kept us from making a real connection on the first two dates. It was like he was holding back. I feel like I have a great sense of humor and I love to have a good time, so I wasn’t sure I wanted to date a guy who couldn’t laugh at life and laugh at himself, so I still wasn’t sold, despite the attraction.

Since he kept asking me out, I assumed Bill was interested, but he had me guessing.

When Bill asked me out for a third date, I told him to meet me at our local amusement park. I wanted to get him out of his comfort zone and see if he could have fun.

So we get to the theme park and start to ride rides. Bill seemed to be having a good time, but I still felt like he was holding back somewhat. I had just about decided that Bill was reserved and didn’t have much of a sense of humor, so I figured I didn’t have much to lose with my next ploy.

I bought one of those disposable cameras and told Bill I was going to take pictures of us throughout the evening. Eventually, I maneuvered Bill near the fence of the one water ride in the park, right were the water would splash when the ride came by. I timed it just right where Bill would be standing in the way of the splash. It was getting dark, so I don’t think he saw the big wet spot.

I hold him in that pose and suddenly, whoosh!, Bill is soaking wet. I think he’s going to get angry at first, but he looks at me and starts dying laughing. I feel sorry for poor Bill, so I confess to him. Bill jokingly tells me he’s not going to suffer alone, so I agree to go on the water ride with him (I usually hate the water rides at roller coaster parks).

So there we are, each soaking wet. The park is clearing out by then and it’s a warm summer night, so the water actually feels refreshing. We made 4 or 5 other rides and we have a blast. I get scared on the tall rides, so I’m hanging onto his arm screaming the whole time (maybe I’m playing it up a little). The water splash seems to have transformed Bill and he completely loosens up, joking and laughing the whole time. He took my teasing the right way.

The last ride of the night, Bill suggests we go on the slow ride in a dark tunnel. In the middle of the ride, we start to make out. We go home, both still sopping wet, and make out when he drops me off. It was actually pretty erotic.

We got pretty serious after that and we’ve been dating for just over a year now. It turns out that Bill has a brilliant sense of humor, too. Bill later admitted he was a “little shy” at first, because my smart-alec tongue and hot-hot looks made him think I was stuck up or judgemental. Not at all, not at all: I’m in love.


More Cute Date Stories

So there’s a couple of cute little date stories. If our readers have cuter date stories to submit, I encourage them to contact this site and we’ll print your date stories. People love these things.

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