Have you ever been on a date with somebody that seemed like a great catch when you met them but at some point during the date they say or do something that completely ruins it in an instant?  To celebrate Valentine’s day this year I wanted to share some of the unfortunate dating incidents that my friends and I have experienced over the last several years.  These are the moments that seem awful when they happen but in time they make some of the best stories shared over a glass of wine!  Names have been changed to protect the innocent.

The MultiTasker…  I met Richard on the dating site, Plenty of Fish.  On our first date, after enjoying a great dinner, Richard and I stopped at a bar for a drink.  We had just settled in at the bar and ordered our drinks when he pulled his phone out and started scrolling.  Richard:  Do you mind if I check my dating site emails while we wait?  Me:  No, go ahead 🤷.  He proceeded to show me the profiles of several different women he’d been messaging with!

The Zombie…  Steve and I met for a walk on a nature trail for our first date. Halfway through the walk, I had already decided Steve was headed for the “Reject File” and was preparing an excuse to get out of any further dates if he asked. We were almost back to the parking lot when he stopped to get a pebble out of his shoe. When he took his shoe off he had no socks on and I got a glimpse of some long, jagged, brown, fungus riddled wooden-looking toenails! I heard the Jaws theme song playing in my head as I ran for my car! 🏃💨🦈

The Comedian…  I had a few dates with James who was two years younger than me.  He made a couple of jokes about dating an older woman and I laughed.  And then a few jokes about aging (not so much laughing).  And then a few jokes about me being a cougar (oh, he has no idea!).  And then more jokes about my age.  I finally had to tell him it really wasn’t funny anymore.😐

The Sicko…  My friend Miranda went on a date with a guy named Sam for dinner and drinks one night.  Later, back at her place he leaned over to pet her dog and threw up all over poor Rocky!  That was the end of Sam!

The Distracted…  Don was an extremely good-looking, sweet guy that I dated for several months but if I had to use only one word to describe him it would be “distracted”.  He couldn’t focus on any one thing for more than a few minutes.  One time, right in the middle of having sex, he began rummaging around in the nightstand.  Me:  What are you looking for???  Don:  I was just getting a breath mint!  Me:  😶

The Cross-Dresser…  I received an email on the dating site from what appeared to be a woman.  Raymond was actually a man but he informed me he just liked to dress like a woman.  He tried to convince me he was the best of both worlds because he loved doing his hair and makeup and going shopping but he is still a man and he is still attracted to women!

The Ditcher…  My friend Lucy told me about one of her epic-fail first dates with a guy named Dave.  She had known him in high school but hadn’t seen him in many years.  He picked her up at home one night to take her to a local bar where they were going to have a drink and re-connect.  An hour or so into the date his phone rang and said he had to step outside to take the call.  He never came back!  Lucy couldn’t believe her old friend would just leave her there since she didn’t have a ride home (it’s not like we’re teenagers anymore).  Luckily, some of her friends arrived and when she told them what happened they offered her a ride.  They stopped at another bar on the way home and when Lucy walked in, there sat “Dave the Ditcher” at the bar!  She said neither one of them said a word to each other as if they didn’t even know each other!🕵️

The Handy Man…  I met Randy on a dating site and we went to a movie for our first date. By the time the movie was over I felt like I’d been in a wrestling match just trying to keep his hands away from places they shouldn’t be. After the movie Handy Randy wanted me to go back to his place. Me: No way! We barely know each other! Randy: How else are we going to get to know each other? Me: 😶 (sometimes I’m just speechless)

The Dummy… My friend Samantha (who is never speechless), once told a guy after a particularly bad date that he should go home and Google “Dating for dummies”. 😂😂😂

The Ex-Files…  Barry was a recent divorcee whose idea of a first date with me was much like going to an appointment with his therapist.  He really purged!  By the end of the night, I had learned nothing about him (except that he needed counseling) but I knew EVERYTHING about his ex-wife, including her bowel problems. 💩

The Douchebag…  My friend Charlotte had a similar experience on a first date with Mitch from Match who monopolized the dinner conversation by bragging about all the money he had and how boring sex had been with his ex-wife (even though he’d had five kids in five years).  He went into details about the sexual adventures he’d had since his divorce because apparently, he hadn’t Googled “Dating for Dummies”!  Charlotte thought the dinner would never end! Several times that night he mentioned “their next date”.   As if!!!


The Morbid…  Ryan was coming up with suggestions for our first date and wondered if I would be interested in going to a museum where they were having a cadaver display! 🤓

The Economizer…  One cold Winter night Steve came to pick me up for our second date.  When we got back to my place later that evening I noticed it was very cold in the apartment.  Me:  Wow, it feels really cold in here!  Steve:  Yeah, I turned the thermostat down before we left.  Me:  😲 (My thermostat?!  In my home?!  Without asking me?! It was only our second date!!!)

The Rabid…  I was mowing the lawn one day when Shawn showed up (way too early) for our date that evening. He got out of the car and I immediately noticed he had foamy spitballs, about the size of a pea, on each corner of his mouth. The thought of possibly having to kiss him made me want to mow my foot off so I wouldn’t have to go on the date. 😝

The Buzzkill…  Larry was someone I dated for awhile and had grown quite fond of… until we had this conversation.  Me:  I’m trying to write a book, it has been one of my life-long dreams.  Larry:  Let me ask you this; what if you write this book and you don’t sell one single copy?  Me:  Well I guess I can say at least I tried! (and thanks for the vote of confidence!)

The Desperate…  When I met Stan I didn’t really feel attracted to him but I told him we could start out as friends and see what happened.  After six or seven dates I realized he was very needy and clingy and I thought it was best to end things with him.  After I broke things off, he sent me a bunch of nude photos of himself,  just in case I was ending it because I didn’t think he was a sexual person!  😳

The Fruit Loop…  Roger was another guy I met online.  We lived a good distance apart and planned to meet in the middle at a State park for a hike.  I jokingly told him I was a little nervous meeting a stranger in the woods and hoped he wasn’t a serial killer.  When he arrived for our date he handed me a box of cereal.  Me: 🤔 (cereal???Roger:  Cereal, get it?  Because you thought I might be a “cereal” killer!

The Player…   After our first sexual encounter (which admittedly was pretty amazing), Anthony held me in his arms, gazing into my eyes with great tenderness and concern.  Anthony: Don’t fall in love with me.  Me: 🙄 (see what I mean about ruining it in an instant???)

The Dumpster Diver…  Dick (not his real name but should have been) was a retiree I met on a dating site.  Turned out he wasn’t retired, he just didn’t work anymore.  Dick was in his upper fifties, lived with his mom and existed on the earnings he made selling junk that he found digging through dumpsters.  He acted like a complete jackass on the date and when he called to ask me out again, I told him I wasn’t interested in a second date.  He was very angry and accused me of using him for a free dinner!  I met him the next day to give him the money for my portion of the dinner (a refund, if you please)!  The whole date was a story in itself, the link to that story is here:  https://runningdownmydreams.com/2017/02/26/online-dating-disaster/

Happy Valentine’s Day to all of the guys who made this blog post possible, all of the lovers in love, all of the singletons still looking for love and all the people who have just decided to love themselves! 💘