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The most embarrassing first dates I’ve ever been on…

I was so scared to go on my first, grown up date. Boys had asked for my number while I was working behind the bar and I had always felt too anxious to ever pursue a date or even a text message. It’s awkward. You don’t know a thing about them. Your mind goes to the absolute worse like, ‘what if he is a Ted Bundy 2.0’ or, ‘what if we go on a date and it’s just complete awkward silence’.


I had recently watched an episode of love on the spectrum. And I had thought to myself, if people with major social anxiety and little understanding of social cues and situations can go on dates, then I, a confident 18-year-old can go on a date for an hour or two and hold a conversation.


I thought of a few tips to share that allowed me to overcome the anxiety I usually feel when getting ready for my first dates.


Firstly, ALWAYS choose something to wear that you feel confident and comfortable in. If you feel self-conscious or uncomfortable in an outfit, what you look like to the person you’re going on a date with will be at the forefront of your mind the whole time. Your outfit being the centre of your thoughts will make your mind foggy, making it difficult to think of more questions to get to know the person better. Or it may disadvantage the ability of thoroughly listen to the other person. All you will be able to think is, “is my stomach out too much, are my boobs out enough ;)… wow this wedgy is really far up there!”


Keeping conversation flowing with just two people for a solid hour is surprisingly quite tiring. It takes it out of you. Always have a good sleep before a first date. Your body needs to have lots of energy to be pumped and keen to meet and learn about a new person. Whilst your mind needs to be well rested, so it can concentrate on the person.


I always set ‘time limits’ for my dates. When I arrive, I always apologise and tell the other person that I can only stay for two hours and then I have to go to work or a family event. This may sound rude, but I do it so if worse comes to worse I always have a reason to leave. It also always put my anxious mind at ease when I’m on my way to the date, knowing if it goes badly, I can rely on the thought I only have to be there for two hours. And if the date goes well, then you can make sure to organise a second one! Side note: if the date doesn’t go well (and more will probably go badly rather than amazing) that’s okay! You don’t know the person; you don’t owe them anything.


And if you ever feel like your first date was awkward, didn’t go well or embarrassing, I would like you to read these following stories that have happened to me on first dates that will make you feel sooo much better about your first date experiences.


The first story wasn’t necessarily on a date but still equally embarrassing. I met my friends really, REALLY attractive male friends at knock off drinks the one night. Prior to meeting them I had eaten a leafy pizza (which was my first mistake, greens do not belong on pizza). After spending a whole three hours with these new, sexy men I went home happy with my conversation performance and chuffed with myself, knowing I had held hilarious banter. Once I had arrived home, I went to the bathroom, gave myself a Joey Tribbiani ‘How you doin?’ in the mirror, thinking I was so much of a catch, just to see a big bit of green leaf stuck in the middle of my teeth. It was then I realised maybe my banter wasn’t so funny. Instead, I was just funny looking. They were laughing at me, not with me…


Another time, I was on a second date with a guy. On the first date he had gone for the kiss (well, so I had thought) but I swerved, seeing as it was a coffee date, and I wasn’t going to run the risk of coffee breath. By the time the second date had come around, and we had had a few drinks, I had hyped myself up for a goodbye kiss. My thoughts were, if he had tried the first time, he was definitely going to try a second time, right? Well call me confident, because once my Uber had pulled up and we were saying our goodbyes, I went in for the kiss. It was like time had slowed down. By the time I had I realised he was going in for the kiss on the cheek and I was going for a make out kiss, it was too late. Even to this day, when I think about this moment, I watch it in slow replay in my mind from the people walking along the streets point of view. A slow motion, outer body experience of me looking like a fuckin baby bird and him as my mother bird trying to feed me, as my open mouth devours his pouted lips. After the worst of it is over in my mind, the memory speeds up to normal time yet I remember getting in that Uber so fast and making the driver speed off, slouching into the car seat feeling as embarrassed as ever.


The next story again wasn’t a first date but still an extremely embarrassing story that makes me cringe to think about. This guy, let’s call him Craig because no one below the age of 30 years old is called Craig and it would be creepy if I was talking to a 30 year old. Anyways Craig and I, had been talking for some time and would occasionally call each other to catch up. I had called him on my drive home from somewhere and he hadn’t answered. I was a little bummed so when I got home, I overshared to mum saying, “ohh i was driving home and I said to my phone ‘Hey Siri, call Craig’ and he didn’t answer which is a little embarrassing, but oh well.” Little did I know, when I was retelling this story to mum, my phone was sitting about two meters away from us, and it starts calling Craig again because it heard me within my recount say to mum “Hey Siri, call Craig”. Not only was I now embarrassed that he didn’t answer the first time. I now looked desperate calling him twice!


Finally, on another first date, a guy was very sweet and picked me up to take me out. During the car drive we were listening to his music when old school Pink came on. I was very impressed; I love old school Pink! But then I asked him if he liked her newer, over played song that is on the radio all the time called, ‘Cover me in Sunshine’. He said, “yeah I know it, but I forget how it goes, could you please sing it for me?” Me, a shower singer ONLY, then had to hum and speak the lyrics so he could remember how it went. He then proceeded to say, “no, sing it! I don’t know how it goes when you say it like that.” So, after sitting in this guy’s car for no longer than 15 mins he didn’t know what school I went to or that I have a pet dog but instead knew, I had a horrible singing voice.


So, I have had some very bad experiences on first dates, or just getting to know guys in general. However, I’m still alive and laughing at those experiences I’ve had. They haven’t stopped me from getting out there and getting to know new people. If anything, it gives me room for improvement within my first dates. First dates really aren’t that scary, and with those tips and tricks above, you will nail your first dates!


That’s my ramble.

Ruby x




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