Showpo HQ Divulge Their Worst Dates

What's yours?

Ever had a really fucking terrible date and left it wondering how the fuck you got there? Similarly, ever listened to your gal or guy pal’s dating horror story and wondered why bad things happen to good people?

You’re not alone.

I’m not a huge dater myself, I love the idea and really think it’s a great experience but I’m awkward and hate small talk, which makes going out for a drink with a complete stranger a bit of a trainwreck. Honestly, I’ve tried.

However, I don’t need to be tearing up Tinder to know that the dating world is a minefield of the good, the bad and the kooky when it comes to experiences.

So, I asked some of my office pals to share their worst dating experience and, whether they be cringe, gross, rude or just a lol, here are some of the worst dates Showpo peeps have been on.

The poor man…

I don’t usually date but the one date I did go on he basically spent the whole date telling me how poor he was.

“Isn’t your handbag like really expensive?”

“I don’t have an iPhone because they’re too expensive”

“Are you alright to get your own drink?”

“Can I jump in your uber and drop me at mine on your way home” – Bambi, Stylist

He was like 26 yrs old minimum – get your life sorted mate…


Too close for comfort…

My date drove me to the top of a mountain in Athens with a bar at the top (off to a cute start, right?). We were drinking our beers at the bar, looking out at the view when he reached under the table, squeezed my calf muscle and whispered “bravo Alejandra”. I hate being touched! He then asked me how much I worked out as he stroked my bicep! Ewwww.

The worst part was that because he drove me to this mountaintop, there was no way for me to escape!”    Alex, GM

Just what every girl wants on a first date – an invasion of their personal space AND to be referred to as a masculine figure.

Too soon?

I spent a date talking about my boyfriend with his parents and telling them how much I really liked their son, John. Turns out the boyfriend was called Andy…..oops.” – Christa, Graphics 

Word to the wise – if you haven’t managed to memorise your date’s name, it’s probably too soon to be meeting the parents.

The classic fuck up…

I took my vegetarian girlfriend to a best mate’s birthday at a rib house, completely forgetting about her dietary requirements. Not happy, Jan.” – Frank, Dev

Ahh the classic new veggo girlfriend fuck up. Make your new girl unhappy AND make your friends think she’s high maintenance in one swoop. Nailed it.

The freakshow…

I went on one date with a guy then, being the charming guy he is, he continued to woo me with revoltingly romantic texts and two bunches of flowers to work in the space of one week only to then ghost me because I was “too much”. MATE, you sent ME two bunches of flowers and started talking about our long future together and I’m too much?

This entire emotional rollercoaster lasted a total of 3 weeks…”  Chelsea, Buyer

The creepy kisser…

Third date with a girl. She was nice enough, my spidey sense had been tingling about something but I was rolling with it. We were at my place, hanging out having a nice time. I went for a kiss. All good. After a little bit, she looked at me and said: “I really like it when you kiss with your eyes open, it’s really intimate”. Ooooooooooook. Not what I normally do, but I’m an open-minded guy. So I try. Of course, I give up after about 5 seconds of kissing. I apologise, say I can’t do it. She insists. Ok, I try again. Of course, still can’t do it. I tell her again. She insists, again. I say it’s a no go. She can’t stop talking about it. Moment = destroyed. I tell her it’s not going to happen but she just kept going on about it and I just had to ask her (in a raised tone) to leave.  I was one step away from calling the cops when she finally left. She then went on to leave a voicemail the next day saying she was sorry for any offence she ‘may’ have caused…I sampled the clip for a song.” – Steve, Marketing 

Needless to say, there wasn’t another date…..

The persistent one…

Through a friend of a friend and some convoluted circumstances, this guy (a friend of a friend) ended up with a book of mine. So I got in touch and arranged through about three bland messages to meet at Korean culture festival for me to collect it – nothing date-like, I just assumed that’s where he’d be at the time and I really needed my sister’s book back. So,  I dragged my sorry hungover arse on a Saturday morning (hungover from a date with the guy I was actually seeing the night before) to the festival only to arrive to him telling me he’ll give me the book after the festival. I quickly realised the misunderstanding and tried to save face by chatting politely – he did bring the book back after all.

Anyway, after about an hour I said I needed to head off but as my house was nearby he asked if he could hang at mine to wait for his bus (how do you say no?). Once arriving at my house, I offered him a glass of water which he declined but then proclaimed he was “going to take a nap” and started napping on my lounge like we were old friends! After about 30 mins of laying on my lounge asking me to come over and ‘nap’ with him, and me saying no thanks he got the point and decided to leave. Finally!

I found out weeks later he told our mutual friends that I was awkward and boring and really didn’t seem like I wanted to be there…YOU THINK?”  April, Marketing 

Note – if you exchange a few batshit boring messages with someone to return some property does not mean they’re into you or owe you a date.

The Instagram photographer…

I met a guy from Tinder for one drink and as a ‘photographer’ he told me that my right side was my good side and I should only take my selfies from my right side (I didn’t ask). Then, he asked to see some of my selfies. After a drink, I politely said I wasn’t vibing it but nice to meet him and he got really pissed off and said that you need to stay a whole date to see if you like someone. Mate, what?”  Jords, Buyer

Are you suuuuuure you need to stay the whole date?

Mummy’s boy…

I went on a date with a guy and he asked me where I saw myself in 5 years (is this a job interview?) to which I replied “maybe overseas, definitely somewhere that isn’t Sydney” and then when I asked him the same he said “Still living with my mum hopefully”. – Kate, Marketing 


The squid…

I’d been chatting to this chap for a week or so and he looked *pleasant enough in his pics. The conversation was reasonably witty and when he suggested meeting up for a drink one night I didn’t see why not.

When he came up to me my heart sunk. I realised I’d fallen victim to the ol’ ‘pics are 8-10 years old’ trick some gents choose to employ.

Regardless, I would never be rude and you never know when you might make a new pal, so I went in and ordered a drink.

What followed was one of the blandest conversations I’ve ever had. I held most of it and even the smallest quip had him guffawing loudly as his jowl quivered in unadulterated excitement. At one point he sternly told me I was at the appropriate age to settle down and get married as I was getting on in the ovary department.

Maybe some lasses like to hear their biological clock is running out as a form of foreplay but at 26, I wasn’t impressed. I decided not to drink anything further in an effort to wrap things up but he was downing them like water and seemed to think the date was going swimmingly.

I got back from the loo at one point and he’d actually shifted his bar stool from across the table to next to me. He was trying to inch closer and closer, invading my personal space to an inordinate amount. I was leaning away and he was leaning in and then as if a bad rom-com had predicted it, I toppled right out of my seat. Cue, a flaming face while he sat staring at me (probably thinking ‘well she’s clumsy so probably not this perfect wife I was envisaging’) as I collected myself.

After 1 long hour and 17 minutes, I wrangled an excuse to leave and he offered to walk me to the cab rank. **My polite ‘oh you don’t have to’ was obviously rebuked by this gentlemanly investment banker who JUST WANTED A PRETTY WIFE DAMITT!

It was during this walk that he deemed it appropriate to wrap his long tentacles arms around me and go in for a kiss. What ensued was an awkward 35 seconds of me trying to loosen his grip while I politely giggled and continuously moved my head around in circles so he couldn’t plant a smooch on my unsuspecting lips. Then I beelined towards a cab and rode off into the darkness.”  Kelly, Government Official 



HA! I told you dating was a good experience. In all honesty, I do think meeting someone outside of your normal bubble as well as trying to explain to someone outside of your bubble who YOU are is good for us! BUT, it’s a jungle out there – be careful ladies and gents.

Curated lols - April Murphy. 

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