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Any kind of dating can result in funny stories, even when we are looking at married dating. Not every couple works out or has rigid barriers in their relationship. We talked to five people that tried to get involved with married dating and had hilarious results. Use these stories to remind yourself that romance does not have to be so serious.


     1.   Wanna Get a Drink?

“I decided to sign up for a chat room for married people to branch out a little since my wife and I were together, but not really. I met someone named Casey, and we hit it off immediately. We liked all the same things, she worked in the same town as me, and we wanted to see what to make of the situation. I was waiting at the bar talking with another guy, and he says he’s there to meet this woman named Maxine. Long story short, we both learned a valuable lesson about unisex names that day. We laughed and got a few drinks together at the bar.”

     2.   Go for a Swim

“It was my first time going out on a date when I was in the process of divorcing. I was invited down to a marina where I would meet my date and go out on his boat with a bunch of other people. We were on the water, I had a couple of drinks, and then we went back to watch the sunset at an upscale restaurant. Wouldn’t you know that I went to step off the boat, tripped, and fell over the other side of the dock? Completely ruined the night and the date, but we laughed about it later.”

     3.   A Hall Pass to Remember

“My wife decided to give me a “hall pass” for our 10th anniversary. We had been high school sweethearts, so I was just about 30 when I had the opportunity, and I wasn’t going to pass it up. I met someone on a dating site that was looking for a fling and no strings, so I was immediately on board. We decided to skip all the dates and just meet up at a hotel. I got to the room, texted her the room number, and heard a knock. I open the door, and there is my 10th grade Math teacher wearing a tight black dress. It might not have been so bad if I didn’t go ‘Mrs. Smith’ right away, but needless to say, I didn’t use my hall pass that night.”

     4.   If You Like Pina Coladas

“My wife and I were going through a rough patch, and we agreed that we would see other people and try to come back to the relationship somewhere down the line. I scoured dating sites because I didn’t know how to ask someone out after so many years. I met this woman that was so much like me that I felt comfortable enough to reach out to her. We were both stunned to learn that this was my wife. We stayed together.”

     5.   Like Riding a Bike

“The bad thing about dating as a married guy is how quickly you forget to be a civilized person. I got a date after what felt like forever, and I ruined it. I went to the restroom and came out with my shirt tucked into my boxers. What a sight that must have been for my date. Guys, if you’re dating while married, brush up on how to dress for a date again.”

Married dating is a serious topic, but people can have fun experiences with it. These men and women had unique experiences that made married dating funny and fun. You should give it a shot and try to avoid the same issues they ran into!

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Funny Dating Stories with Married People
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