The Top 5 Worst Dates I've Ever Been On

When I decided to be a dating and relationships blogger, I thought it was because I’d really seen it all, or least a huge portion of what was left to be seen. But today I realise that a year ago when I decided this would be a good idea, I hadn’t seen anything yet.

Last week as we celebrated the newfound citizenship of a dear friend, I energetically recounted the latest story of dating drama to one of my best friends and his girlfriend. They laughed enthusiastically (with the most infectious laughs you will ever hear) at my trauma, telling me multiple times I needed to sit down and pen a book recounting all my tragic experiences because I had some other kind of crazy-magnet attached to me. I laughed at the time, but went home and thought about it some more. It was true. I had a special knack for inviting the weirdos, inspite of all my vetting, my sky-high standards (not even) and my desire to choose a normal human being as even a potential date, forget life partner.

Then I thought, taking a book may take some time, but in the time being, I sure could write a blog post. With that in mind, I think now is as good a time as ever to share five of the worst dates I have ever been on. I hope they bring you some joy for no pain, no gain.

Top 5 Worst Dates of my Life

1. The guy with the hook-up calendar and exclusive penthouse

We’ve all heard of those guys who are successful, well put-together, articulate and good looking. I for sure have only heard of them because meeting a normal one of these men seems impossible for me. This guy was an Investment Banker at one of the world’s top IB firms (no names of course). He was exotic, half-European and half-South-American. He was about 50kg of excess muscle than I had imagined, his Hugo Boss suit (he told me the brand, obviously) stretching across his muscular arms. He showed up to the bar, ordered a $50 shot of whiskey, told me he was busy becoming a massive deal in the banking world and had no time for a relationship. What he did have time for though, was drafting a very intricate hook-up calendar to designate his sexy time days. He asked me for my e-mail address so he could send me a meeting invite to book me in (a month in advance at a time, mind you) and told me we could only hang out at his penthouse in case he ever ran into a woman he wanted to wife. He didn’t want chicks hanging off him apparently, because you know, that’s the first thing a woman would be put off by when talking to this guy. The cherry on top of his cake was that he didn’t like ‘brown girls’ but was happy to accommodate me because he had a preference for ‘Marilyns’ a.k.a women with an hourglass figure. Legit. I essentially told him I’d fall in love with him if I got involved because he was my ideal man. He believed me. I left.

2. The guy with the dead fish

Recently I went on a date with a guy who showed up with a dead fish in an icebox as a present for me. With a bow on it. In his defence, he was a seafood butcher at an exclusive restaurant (which I shockingly discovered midway through the date because he had told me he worked in ‘hospitality and food strategy’). For the first 10 minutes of the date, I really did try not to look absolutely traumatised that he’d brought me a dead Halibut as a gift, mostly because at this stage I was still trying to contextualise it. He then also made several awful fish puns and jokes, including ‘This fish is the freshest catch of the day, like me!’ and ‘What do you call a school of fish selling cookies? Girl Trouts!’ Yes fam, this really happened. Naturally I stayed because I am not a huge jerk, but when he invited me to come into the kitchen at work to see their live octopus tank, I had to make a call (-amari tehehe) and leave ASAP.

3. The guy who choked on the popcorn

This is an oldie, but one of my favourites. In mid-2015 in the midst of trying to re-stablish my dating credibility, I thought I’d it up the finest matchmaker of our time, Tinder, and go on a date with an intellectual, sexy and very tall lawyer at one of Australia’s top tier firms. Instead, I found myself on a date at my favourite bar (I only ever do first dates here because I know all the bartenders and security, safety first people) with a guy who met only one of the aforementioned criteria: tall. Not only had he grossly misrepresented himself in the photos as he was 15kg heavier than expected, he was also wearing a floral shirt with jeans, a blazer and a matching floral pocket square. Being no Jennifer Aniston myself, I have no problems with guys who have a bit of chub, because hello, we’re human beings, not magazine ads. Plus with his height, it looked distributed evenly enough. However, my forgiveness was seriously tested as we sat down to converse and he said several odd things such as ‘How deep do you think that stage is there? Could you fit people under it? Wouldn’t it be nice to be together forever and be buried where you meet someone?’ The highlight however came when he helped himself to a fistful of complimentary popcorn and obviously, choked on it. He then reached to take a sip of his wine to swallow the choking popcorn and ended up spilling it everywhere. He then pulled out his pocket square, cleaned it up, folded the handkerchief and placed it nicely back into his pocket. Top tier law firm, that’s all I can say.

4. The guy who had slept with everyone in the bar

Around the time of the popcorn choker, I also lined up a date with a guy who my friend A described as ‘Game-show guy’ based on his overzealous cover photo with his mouth open in fake surprise. According to A, it looked like he’d won ‘The Price is Right’ and warned me weird things were a-coming. Even still, as I am an optimist (and possibly a masochist now that I’m reflecting), I went on the date anyway as he was also a Consultant at a different tech firm and sounded like a nice person. As soon as we got to the bar and sat down to talk, he begun fidgeting. It was distracting and annoying and I felt like he was looking for the exit every time he looked behind his shoulder. I soon discovered that it was not me he was not interested in, but rather, saving himself from coping a major glassing to the face. When I finally asked him exasperatedly what he was looking for, he sheepishly confessed that he’d slept with not one, not two, not three, not four, BUT FIVE of the women in the bar and sure enough, hadn’t called a few of them back. They had now spotted him (and of course they were all friends, not the brightest bulb in the box) and were death-glaring him something fierce. He requested if we could leave and go somewhere else. I refused and told him to cop it like a man, SOLO, because I was leaving too. The best part of this story is a few months later, a CV ended up on my desk to review for a potential consulting candidate and lo and behold, once I did my recon work, it turned out to be this guy. I put it straight through the shredder.

5. The guy who I didn’t realise I was on a date with

Last but absolutely not least, a Consulting peer from a rival firm I’d met at a networking drinks when he accompanied my friend, asked me to a drink in the city on a Friday night. I didn’t think very much into it, thinking we were simply catching up as consultants often do to keep work options open and considering we’d only spoken twice, once at the event, once via e-mail. We met up in the same bar as always and the conversation flowed naturally. What started out as work chat quickly turned to exploring interests in one another’s lives, talk of families, friends and inevitably, relationships and of course, love. As we talked about terrible relationships and I recounted some of the above dates to him, he found it somehow appropriate to grab my hand across the table. I looked down in shock, then back at him and blinked profusely. This guy was 9 years older than me and I’d assumed he’d been dating my friend for over 6 months. I pointed this out to him and he looked back at me in utter surprise. He was not in fact dating my friend at all, but had been elaborately trying to get her to set us up for the last 2 months since the networking drinks. Once I got over my surprise, I told him I thought this had been a friendly catch-up to discuss work opportunities. He looked beyond devastated. At this point, he proceeded to unhook his fingers from mine and got up, leaving the bar and me with the bill. Needless to say, I was not impressed. This date actually had a lovely end because he did eventually apologise, offer to pay me back and take me out for a very professional drink. He is also now actually dating my friend!

So there you have it.

When I read back, there’s no doubt in my mind that somewhere along the track, I must be doing something vehemently wrong to attract this kind of attention. Nonetheless, it does make for absolutely hilarious content.

Let me also just end this post by saying, these dates above don’t include the guys who don’t show up at all, because I’d much rather an awful date than a Houdini. It also doesn’t include the guy with the pet rocks, because he’s in a league of his own. Make sure you catch-up on reading that one if you haven’t.

Till next time!

R xx