Storytime - Dating Disasters!

So, we’ve all got some dating horror stories, so I’m here today to share a couple of disastrous dates from my past with you that might make you cringe a little, might make you laugh or might just reassure you so it’s not just you. Trust me, it’s easy to think that it’s you when it happens, but it’s totally not. There’s not a person who’s ever dipped their toe in the dating world who’s not got at least a couple of occasions they wish they could forget. In fact, why don’t you share some of yours in the comments?

Ok, so storytime!

Back when I was about eighteen, I was still naïve enough to think that any man who asked me out could be Prince Charming and that life could be like a modern-day fairytale. I’ve not quite had all my optimism squashed out of me, but god, young me was like a dumb little puppy. A puppy who made some stupid choices back in the day.

Dating was a different game then. The online dating scene was just on the rise and social media didn’t exist. Gay life in my small town wasn’t exactly booming, so a monthly party night in a tiny dive bar was the best we had. On one occasion, I met a guy at one of these events where I thought I might try actual dating instead of the ‘mostly sex’ encounters that I’d been doing. Hey, I was eighteen, you’ve got to experiment!

So, let’s call this guy ‘John’ – I’m saying that because I can’t actually remember his name. It’s been a little while. He was tall, big, broad shoulders, tan, clearly worked out and very well dressed. He seemed pretty well educated and appeared pretty successful judging by the expensive clothes and accessories (not that I’m shallow – though maybe slightly when I was younger). He really semed like the full package! Hot, rich, intelligent, what’s not to love? Well, actually, probably not that much now, as what I can remember about his personality is practically the opposite of what I go for now. John invited me on a lunch date after we swapped numbers while chatting at the party. He was clearly trying to impress me, as he took me to a notoriously expensive restaurant in town that I’d only heard things about. I remember agonising about what to wear, finding formal occasions awkward but wanting to be dressed up for the place we were going. Being still around the age of teenage rebellion and being desperate to be edgy and individual (it was the early noughties, that’s how we rolled) I refused to conform and go with a shirt and tie, so I think I went with a cool t-shirt and my nicest leather jacket and some slightly dressier jeans. He might have liked me for my quirkiness for all I knew!

I needn’t have worried about the outfit too much, as it didn’t really matter in the great scheme of things. I arrived, early for once and incredibly nervous. We went in and everything was actually going pretty well. The menu looked good and he ordered some wine and let me know lunch was on him, as he did the asking out. Obviously being polite, I didn’t go expensive on the menu, so went for one of the burgers on offer. The wine arrived and he impressed me with some facts he knew about red wine, having been to where this bottle was from. I was enthralled by this attractive, classy, worldly man in his thirties (who, to me at the time, was an ‘older man’). Everything was going so well, despite my nervousness. I felt only mildly out of place, but I’d watched enough rom-coms to know that this was how a first date was supposed to go. He did a lot of the talking and then talked about some of the guys he’d dated (which should’ve been a warning sign) and then it came. He broke the spell.

In the middle of his monologue about his previous dates, he decided to tell me he normally only goes for Mediterranean or tanned muscle men. Cute, we all have a type, I guess. The problem was, I was clearly neither of those things. So I asked, playfully, “How come you asked me out?” followed by a nervous chuckle.
Then came his reply. “I thought I’d try a chubby, less impressive guy for a change.”

Wow. That was quite a reply. I looked at him in silence for a second, expecting it to be a joke and for him to laugh. Not that it would have been that funny, but I can take a joke. For all my youthful bravado, I still had the odd weak spot in my confidence and that had been right there. Sensing my confusion and lack of the right words, he doubled down on what he’s said and basically explained how it’s apparently ‘easier when you’re the hottest person in the relationship’.

So for me, any romantic feelings promptly evaporated and his audition was pretty much over. That was absolutely not how to impress someone on a first date. Now, I completely acknowledge that I could have reacted better, not that he deserved better, but if you’re going to insult someone while wearing a pastel pink blazer, it’s probably not a good idea to order red wine. Not one to enjoy wasting booze, while I thought of what to say, I quickly guzzled the rest of my glass and placed it on the table. He sat there beaming at me like I should be grateful to be in his company, so I rewarded him by slowly reaching across the table toward his hand, but instead of grabbing his hand, I took his freshly refilled glass. The food was just arriving at our table as I threw his wine in his face – and all over his ‘lovely’ pastel pink blazer. I grabbed the burger off my plate with one hand, picked up my jacket with the other and left, taking one last look at the red wine soaked table, slimy date and previously pristine and mostly white corner of the restaurant as I told the waiter “He’s paying.”

I left, not seeing how I could actually stick around. I’d put on a brave, or just angry, face but as soon as I was a safe distance away, I was more upset than I thought. I only managed one bite of the burger before binning it and going home to be alone. It wasn’t that great. Overpriced and chewy. Perhaps my date did have something in common with at least one piece of meat at the table that day!

The other dating disaster wasn’t nearly as dramatic, but still manages to surprise me even years later.

I’d been on an early online gay dating site and met a local guy in the chatrooms. It was quite rare to see someone near my own age, so we got talking. I was probably about eighteen or nineteen at the time and we hit it off and were chatting for hours. We met up in the chatroom another couple of times that week and chatted privately and swapped numbers eventually and then we arranged a date at a local coffee shop. I wasn’t going formal for a date again after the last one!

We’d spent ages talking about jazz music, since we both enjoyed it and he said he’d bring a tape to the date of a jazz musician he’d been telling me about. A tape. You can tell this is a good while ago! I was excited! This guy seemed lovely.

The day arrived and we were both nervous but managed to have a pretty good time. It was nice. Then came the time he had to leave and he reached into his pocket and handed me the tape. I told him I’d listen to it as soon as I got home and we’d chat soon.

So, I got the bus home and was looking forward to listening to the tape. Side one was great, so I eagerly turned it over for side two and was completely surprised.

On side two was not a continuation of the music I’d been enjoying, but a message. The worst part was I could tell it had been used before because of the clicking and sound change before and after my name was recorded into it.

“Hi, my name It was nice to meet you today, but I don’t think we’re going to work. If you could delete my number and not talk to me again, that would be great. Bye.”

So, not only was he ditching me BY TAPE, it was clearly a pre-recorded message that he’d used before! The biggest question was: Would I have still gotten the music if it had worked out? Did he bring two copies? One for a good date, one for a bad? We’ll never know. I never saw him again and I can honestly say dumping or being dumped in person is the only way to go. Tape was a weird way.

Fortunately, I’m a little more comfortable and experienced these days. Though there’s still a cute, nervous vibe on a first-time romantic encounter, but that’s how its supposed to be! Don’t lose that, no matter how many bad dates you go on! Now, I wonder if the rugby player I sent home wearing my lipstick last night will call…

So, there’s a couple of my dating disasters. No wonder, I’m more cynical these days! Why don’t you share some of your funny or weird ones in the comments!

Stay Safe, Stay Sane, Stay Vidalicilous x

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