6 Hilarious Wingman Fail Stories - Halloween Special

Love it or hate it, our friends and family will do whatever it takes to help us find love.

Good intentions go a long way but epic fails will forever be remembered. Here are some of our faves – Halloween edition:

1.     Slip + slide

“I had a huge crush on a guy who worked at my local store and my friend being the extrovert she is, dragged me there one day with the intention of setting us up. She’s known to be quite a good matchmaker in our friendship group because of her excellent social skills so I figured I’d go along with it. 

When we got there, we noticed they had a huge display of pumpkins for Halloween so the geniuses that we were, we asked my crush to come help us find a good one. While he reached to get one from the top, to our horror, the whole stack of pumpkins fell on him nearly crushing him to death. My friend thought I could be his "knight in shining armour" moment and nudged me towards him – except I ended up slipping on a piece of pumpkin and head-butted him as he was trying to get up. 

Needless to say, we both haven’t stepped back into that store!

2.   Dracula’s long lost cousin

“Me and the boys went to our favourite spot one Halloween where one of my friends spotted a suspiciously cool red drink they were giving out for free. Never one to say no to free alcohol, I downed them not knowing the horror that awaited me. Turned out whatever was in the drinks stained my teeth red and I looked like we I was part of the Dracula clan – now we know why the drinks were free. To make matters worse, there were a lot of cute girls my friends would introduce me to and I had to pretend to be a moody asshole with the fear of showing my red teeth if I tried to smile. Still waiting to get my revenge on them!

3.     Cupid’s blind assistant 

“My grandma is always trying to set me up any chance she gets. Once I went with her to get some pumpkin pie and as I was paying, the store owner who was dressed up for Halloween, said he was looking forward to our date on Friday. Before I could say “Excuse me?”, my grandma answered “She’s very excited too” and ushered me out the store. She told me she arranged a blind date for me with the store owner! Shocked but not surprised, I decided what the heck, I’ll go and see what happens. 

We ended up having a great date and saw each other for a while. When he came round for a family barbecue, my grandma pulled me aside and asked how we met. I told her she was the one who arranged the blind date for us and she looked at me – dead in the eyes - and said, I thought I set you up with the handsome one. The one with the hair (his brother), not him.  

4. You’ve got to be Joker-ing!

“One time, my sisters dragged me to a “masquerade” singles night where they heard there was going to be a lot of single cute guys in dashing suits. Except, when we got there, everyone was in costumes – Halloween costumes. While my sisters went to the bathroom, I was looking for a place to sit when a guy, I can only assume dressed up as the Joker (looked more like a clown), came up to me trying to break the ice. Apart from the questionable makeup, he seemed quite genuine and we had really good banter. We shared a cheeky kiss. When one of my sisters came back, she had a huge grin on her face, turned out she also kissed someone. We went to find my other sister to see what was taking her so long and we found her kissing – you guessed it – the same guy we had both kissed!

He tried to justify it by saying he thought we were all the same person because we had similar masks on -  except for the fact that we were all wearing something different. Still one of my best Wingwomen stories, even if it was a fail!

5.     Fright night

“Our annual Halloween party is where office legends are created. Last year, the theme was Ghosts and vampires. I was told by my work friend that my office crush was dressed as a vampire and he was standing next to the drinks in the corner. At this point, I had a few drinks and was slightly buzzed (not drunk). Thinking this is the best chance I’ll get to see if he’s up for going on a date, I approached him and got my flirt on.

He looked a bit awkward so I made my excuses and left swiftly. My friend came up to me and asked why I was fliting with the boss and the penny dropped. The guy I actually liked and my boss were both dressed the same, I was mortified! In a strange turn of events, my boss knew it was a misunderstanding and actually broke the ice between us. I became the office legend that night – but for all the wrong reasons!

6.     So long, sucker

“I matched with a girl on a dating app and we found out we had mutual friends so we agreed to meet at a Halloween party one of them was throwing. While I was waiting for her to arrive, I was chatting with my so-called Wingmen who decided to reminiscence about my dating past including everyone I’d slept with.  She never turned up and when I messaged her to ask why, she said she had overheard our conversation including the fact I had slept with our mutual friend. Still wondering if my wingmen saved or failed me!

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Photo by @ClicksdeMexico via twenty20