The Misadventures of Dating


Great dating ideas don't always turn out to be the best in real life. Although we'd all like our dates to be straight out of the movies, real life sometimes makes them awkward and more like comedies. In an attempt to help you feel better about your life and ease some of the pressure of going on perfect dates - our team wanted to share with you some of our "best" experiences in dating. Enjoy!

The “Taxi Driver” Date

“A guy I didn't know super well once asked me out. But about 10 minutes before he was supposed to get me, he asked if I could pick him up because he didn't have a car. I was kind of blindsided, but agreed! Just before I was about to leave to go get him, he asked if before our date I could take him to Trader Joes because he needed to do some grocery shopping. Pretty sure he just wanted a taxi more than a date."

The “Car Problem” Date

"Back when I was in high school and I was out with a girl, the starter on my car died and I had to teach my date how to pop the clutch while I pushed it. I did forget though to tell her how to take it out of gear - and she had never driven before. I pushed, she popped the clutch, and off she went… headed directly towards the bank drive. I had to sprint after her and jump in her lap to stop the car. Later that night, I AGAIN had to ask my 15-year-old date to push my car - so I could pop the clutch and make it home before curfew."

The “Forgot Reservations” Date

"On the first Valentine’s Day, after my wife and I married, I took my her downtown for a nice night out. There were lots of great restaurants so I foolishly thought I could get by without reservations. Obviously, that did not work out well, so a good dose of hangry and frustration kicked in. Completely starving, frustrated and defeated... we went through McDonald’s Drive-Thru and went straight to bed when we got home. Needless to say, there was little speaking and zero cuddling."

The “Forgot My Wallet” Date

"I once went on a date with a girl where I had made reservations at a very elegant restaurant with excellent reviews and a view to kill. That evening, I took an Uber to pick her up and we headed for the restaurant. Food was great and we had good conversations, but then the bill came and I realized I had left my wallet in my room - 30 minutes away from town! What an awkward moment that was! She was kind enough to pick up the check after I shamefully explained my dilemma, and I, in turn, made sure she got reimbursed that same night. Unfortunately, I didn’t get a second date after that."

The “Bragging” Date

"As a joke, my friend signed me up for Tinder years ago. I kept the app for a few days out of curiosity and made it my mission to show guys on there how to talk to a respectable girl. LOL. While I was busy trying to spark revival on Tinder - I ended up caving and going on a date with a guy that I thought was really cute. It was one of the worst dates I’ve ever been on. It ended with him bragging about all his courtside seats and lavish things he gets to do because of his rich friends. He told me, “If you stick with me long enough, you may get to reap the benefits too.” I told him it wasn’t going to work. I learned my lesson."

The “Farting” Date

"One time when my husband and I first started dating, we had had a crazy day of kayaking and adventuring and then decided to end our date with dinner. On our way there, I had fallen asleep in the car and happened to wake myself up due to my own farts. I was mortified but he was amused."

The “Hadn’t Yet Proposed” Date

"Well, there was the time when I was on a date with my girlfriend and I played a voicemail from my spiritual mom. She began talking about how excited she was to meet my fiancé... who I had not yet proposed to!!"

The “Siri-Slip-Up” Date

I was working with a girl I was interested in, but hadn’t yet learned to use my words. So I asked her to “go biking and hang out”. But I was very careful not to say the word “date.” As I finished trying to fix the bike in the Walmart parking lot before picking her up, I realized I was going to be late. “Hey Siri, text Susan.” At that very moment I ran into a friend who asked what I was up to. “Hey, I’ve got a date with Susan and we were going to go on a bike ride, but I can’t fix the tire so now I’m thinking of doing coffee and a walk and I don’t know. I’m running late, I gotta go.” I then look down to text her and realize that Siri had recorded the whole conversation and sent it to her…without asking for confirmation. Siri misunderstood “coffee and a walk” for “coffee and a locker” but it clearly translated “I’ve got a date.” I awkwardly played it off as lyrics to a song. I tried to fix the bike but left the bolt to the wheel at my house so I nervously offered to “run beside her as she rode.” We never made it biking.

The “Nailed in the Head” Date

After going kayaking with my church, my girlfriend said she had a headache. I tried to comfort her and put my arm around her, but I misjudged how close we were. Instead I drilled her in the forehead with my elbow. Needless to say it didn’t help her headache, but all of the sweet old women standing there (who gasped) did. They “blessed her heart” and got her some Tylenol.

Can you top these stories? We'd love to hear your misadventures in dating! (The goal is to get a good laugh.. not to blame anyone.)

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Moral Revolution Team

Special Shout Out to Our Interns & Volunteers who aren’t pictured but contributed some great stories. Their names will not be shared to protect the innocent. 😉