Terrible Date #321: The man with no plan

Olah Lovers!

I am having just the worst luck when it comes to all things sexy time! So much for my new years resolution of having a totally banging year! My first sexual foray for the year was a drunken mess and the second go round resulted in that most terrible of afflictions, the dreaded UTI. To top it all off, I was booked in for a nude modelling class the day I got the UTI so I had to reschedule (very lame). Funnily enough that class was rescheduled for this Tuesday just gone. But no Lovers, sadly this will not be a post about how exciting and crazy it was to be in a room full of thirty naked women throwing shapes and striking poses.

Why not? I hear you ask, a distinct tone of disappointment tingeing your usually sweet voice. Well Lovers, there’s many things you need to take with you when preparing to nude it up for ‘art,’ including a robe (fancy word for manky ten year old flannel dressing gown), water and just a touch of confidence. However, there is one thing you most certainly do not want to bring with you under any circumstances.

Your goddam period.

Seriously Lovers! What are the chances of Lady Red showing up right on that day? Not cool reproductive system, not cool.

I know some of you may be thinking, “but Claire, it was just the first day, surely you could have at least tried to get away with it?” And that thought did cross my mind Lovers, it really did, but the other thought that very soon followed was the image of me, arms thrust high in the air, legs gloriously akimbo, and then a drop of something slowly sliding down my leg…

Ain’t nobody got time for that.

So in an attempt to reschedule (again) I called the art peeps to explain the murder scene in my pants. I didn’t really have much hope however as now it looked like I was one of those annoying people who just wimped out on the day. As I expected, they couldn’t rebook me, but they did invite me to come along anyway and just do the class with my underwear on. Pfft, bitch please, I model in front of the mirror with my undies on every day, where’s the excitement in that? No no, if I was going to do this I was going to do it right dangnammit!

Soo, long story short, there was no nude modelling in my life this week (awww). Instead I thought I would regale you all with a truly horrendous date I experienced late last year!

Where to start? Ok well obviously we met on a dating app (where all truly horrendous dates are born) and he seemed really nice. Normal. Had his shit together.

Oh how wrong I was.

Unlike my usual get in get out technique of asking the usual questions and then jumping straight to ‘beers tonight?’ I actually talked to this guy for quite some time. Weeks actually. Our conversations were fun and something I looked forward to during long boring nights of watching shitty tv at home. Finally, finally though we organised a time to meet. Yay!

And that’s when shit hit the fan.

Literally the night before we were due to meet things just went so weird.

His name was Chester.

Now Lovers, at this point in time I had just been accepted for a job at a call centre booking women in for contraception and other appointments. Needless to say I was bloody excited as this was the first real job I had had that had anything even remotely to do with sex.

Woohoo! Bring on the implanon’s and IUD’s!

I communicated this excitement to Chester and, much to my surprise, he seemed even more excited than me!

Nice but slightly… odd.

When I asked him about it I immediately regretted it. He went on this incredibly long, incredibly intense rant about how his mother had had him at 14 and how contraception and terminations should be free and legal and how “we’re all pretty insignificant in this capitalistic society of greed and bullshit anyway.”

Well that’s… nice… I guess?

Seriously Lovers, nothing turns me off faster than politics. Not to mention people who use words like capitalistic society. Double not to mention when those words are communicated through Bumble, a supposedly carefree and light dating app! I mean c’mon dude, surely this is a conversation to have in person?

Anyways, I tried to lighten things up a little and get the conversation back on track to something a little easier, like “can’t wait for tomorrow, see you then!” Rather than the benefits of abortion and unsatisfactory parenting.

Chester did not take the hint. He said he was sorry for the heavy vibe but then literally a second later was like, “actually I’m not. This is reality, it’s real life, get used to it.”

You’re losing me Chess, you’re really losing me!

Then things got even weirder as the way he had phrased his sentence had me all confused and we spent the next ten minutes messaging, “what do you mean?” and then, “no what do you mean?” which made things awkward as ass. In the end I dropped it and told him I’d see him tomorrow. He finally replied with, “ok, looking forward to some wines and maybe a kiss.”

Now Lovers, in a desperate attempt to keep up comradery (and a little light ribbing) I made a joke. I said, “lol better make sure your beard is clean then!” and inserted many winky faces afterwards.

Not the wittiest of repartee, this I know. However, I feel his responses afterwards were a little uncalled for.

“That’s really disrespectful.” He replied

“Lol how so?” Came my response, desperately throwing in a lol anywhere I could to demonstrate my joking nature (which clearly had not been communicated through the initial message.)

But then he just went ridiculous on me.

“Ok, is your pussy shaven?”

Wtf? Too far man, too far.

I didn’t want to go any further so I pumped the breaks and took the blame, saying, “Ok I feel like I’ve upset you. I didn’t mean too it was just a bit of fun. So sorry, my apologies if I’ve offended you.”

All the while I’m thinking, Jesus if this guy can’t take one little joke about a dirty beard we are not going to get along well!

He didn’t reply. I have to admit I was kind of grateful that he didn’t. I had been in quite the good mood before our conversation; Friday night feels, new job, exciting date planned tomorrow, but he had effectively squashed that right out of me and made me feel completely shitty.

The date was cancelled.

In my head anyways. It was so clear now that we didn’t share any of the same views. I had accepted and even liked the fact that he wore pink a lot (including skinny leg jeans, a pet hate of mine), the fact that he was sensitive enough to walk away from a job where he was being bullied, and the fact that he wore women’s pyjamas because he liked how soft they felt on his skin. I kept telling myself, maybe this is the type of guy I need, someone tuned into their sensitive side, not so manly man like my usual dates.

But after the messages I realised that sensitivity seemed to come at the expense of a sense of humour.

Maybe you think I’m being too harsh Lovers, and in the past guys have labelled me as mean, but in my family, if you can’t take a joke you won’t last long. I’m just prepping them for the future!

So the next day I woke up feeling pretty bummed. I now had no date to look forward too and the guy who I had thought to be some cool, slightly eccentric gent had just turned out to be an annoying political hipster.


You can imagine my surprise when said hipster messaged me asking what time we were meeting for our date.


“I didn’t think we were still having a date after last night.” I replied. May as well be straight up with him, I thought.

“Yeah sorry, I was really tipsy and that subject is always kind of touchy for me. But I’d still really like to catch up. I’ll make it up to you, promise. ”

Hmmm, to believe him or not to believe him? That was the question Lovers.

Fuck it, it’s Saturday, let’s go on a date.

Worst. Choice. Ever.

Chester lived a fair way out of town, and when I say a fair way, I mean it took him two and a half hours to get to where we were meeting.

He was 45 minutes late.


Luckily where we were meeting was a dog park (it was summer, what’s better than watching dogs frolic while you day drink?) so I was able to entertain myself by watching all the pups run around and crash into each other as I sipped my mango beer.

Just when I was about to give up and go home I got a message from Chester saying he was entering the park.

Now you know that feeling you get before a date Lovers? The butterflies in your stomach, the slight tightness in your chest, all smushed together with the wild hope that maybe, just maybe, this will be the last date you ever need to go on?

Yeah, I didn’t feel that this time.

All I felt was the tiny girl that lives in my brain (often named intuition) attempting to jackhammer her way out through my skull, all the while screaming, “you idiot! I’m outta here girlfriend, you deal with this on your own!”

Selfish cow.

I took a long steadying sip of beer and lifted my head to look around.

And then I saw him.

Oh Lovers, it was so much worse than I had imagined. Chester looked nothing like his photos. In fact he looked downright homeless! He had long, scraggly hair that looked like it hadn’t been washed since the invention of shampoo (he had lovely short hair that suited him really well in all his damn photos) and wore a holey shirt with some random band logo on it. He clip clapped towards me in a dodgy looking pair of thongs, with an ancient backpack slung over his shoulder.

Scotty, beam me up now. Now dammit! I don’t want to do this!!

But there would be no beaming, and as I cursed the Star Trek gods to hell, I met Chester with a hug.

Luckily he smelled fine. Phew! Nothing worse than a bit of B.O on a date that’s already going down the shitter.

We exchanged niceties before settling on a bench and cracking open some fresh drinks. Chester had brought a twelve pack of Jim Beam and Cokes doubles. Jesus, how much did he expect to drink?!

I pasted a smile on my face and began to ask Chester about himself. I already knew a lot from our Bumble conversation, but it seemed like he enjoyed saving all the little surprises for me in person. Chester had no job, and no intention of getting one in the near future. Alarm bells starting going off in my head. I don’t need a rich man, not by any stretch of the imagination, but after some of the previous disasters I have dated, I made a solemn promise to myself that I would only date employed men from now on.

Things were not looking great for Chester.

But then he told me about his big dream. Chester was going to be a florist; he’d even enrolled in TAFE course. (However, said TAFE course wasn’t happening until next year as he needed quite some time to “work on himself.” I’m pretty sure that’s man code for “spend most of the day in bed wanking.” But I digress.)

I asked Chester about the course, about his passion for floristry and why he wanted to do it, eager to discover some sense of purpose in this strange man. Was he going to start a business in the end? Travel the world showing off his mad flower skills? Get an apprenticeship at some hip establishment and go from there?

No, none of those.

Chester would do the TAFE course and then, “I dunno, maybe do some shit for friends?”

Wow, what a goal.

I decided to change tack and ask what he did before this, hoping it was just a phase he was going through, an early mid-life crisis if you will.

But no, no luck there either I’m afraid Lovers. Chester had been in quite a few bands. Sounds cool right? Sure, if he had stuck with it at all. He looked at me dolefully and said, “yeah all my mates are pretty big now, touring and recording and shit. But I didn’t. I couldn’t really be bothered. I don’t care though, it’s like whatever.”

Uh huh.

None of this would have really mattered if Chester had had even an ounce of good personality. But he seemed to lack the basic niceties that go with being on a date. There seemed to be no real redeeming qualities in him that I could see. Was I missing something?

All this time ol’ Chess hadn’t asked anything about me, so I thought now would be a good time to fill in the blanks. I tried to tell him about my dreams to become a sexologist, my love for discovering all things fetish and just my general fascination with sex.

Chester however, put a stop to that kind of nasty talk quick smart.

“Look, I like eating pussy and all, but we don’t have to talk about it.”

I hate you.

I’m amazed at this point Chester didn’t see the utter disdain stamped across my face, but he kept on commenting on what a great date we were having.

In what universe was this a great date??

The mind boggles Lovers.

But it gets So. Much. Worse.

Don’t believe me Lovers? Tune in soon for part two of the worst date of 2017!

Claire xx















  1. Gina Daniele · May 14, 2018

    Oh nooooooooo I know where this is headed 😱😱😱😱😱. Run away run away

    Sent from my iPhone


  2. spaniel2u3John Louis · May 15, 2018

    Am I misunderstanding something or was he really complaining about not having been terminated? Did he explain what’s to stop him supplying the deficiency now?


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