First Dates That Were Also Definitely Last Dates

Illustration: Anna Sudit
Though there are many perks to being single, dating is not always considered to be one of them. Picking an outfit, the nerves, making tedious small talk, and that one chia seed you didn’t realise was stuck in your teeth all day are only some of the aspects that make first dates horrific.
First dates can definitely be exciting but most of the time, they’re as nerve-wracking and uncomfortable as a job interview – but with alcohol.
Naturally, no one hopes (or even expects) that it will go badly, but first dates are rarely romantic or easy-going. Dating is truly a mixed bag and for every great date, chances are you might have to endure one (or five) awful ones.
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The truth is, dating is a necessary evil that every woman must encounter at some point in her life. You might meet someone who won’t stop talking about their ex, or who repeatedly calls you by the wrong name. You might also go out with someone who calls himself a “coffee connoisseur” then takes you on a date to Caffè Nero and orders a white chocolate mocha. Trust me, that happened.
The truly terrible dates will leave you seriously considering a career as a nun. But for those of us who aren’t cut out for a life of asceticism, there’s a silver lining in knowing that if you’ve ventured into a date that’s a total waste of time or ends horrifically, at the very least you’ll have a topic of conversation to keep your friends entertained over (many) wines.
Bad, awkward or cringe first dates are almost an inevitable part of every woman's life; even TV and radio presenter Becca Dudley has had one. On the first episode of Freya Lingerie's new podcast When Life Gives You Melons, Becca recalls how on a coffee date, the guy pulled out a box of eggs, scissors, card, Blu Tack and pens so they could paint eggs – and it wasn't even Easter. "I will never forget that," she says, "and 10/10 for thinking outside of the box."
So in the name of sorority, and to let you know you’re not alone in the minefield that is dating, these brave real women share their stories of what could have been but, luckily, never was. Or in the words of queen Bey: “The best thing I never had.”
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Whitney, 30
I’d gone to get drinks with a guy and he was asking all the banal first date questions – what do you do, where are you from, etc. He asked where I went to school and I told him about my nine years of very liberal all-girls school education, at which point he asked with a brutish grunt if that meant “everyone was a lesbo”. I tried to change the conversation but he just kept prodding, wanting to know if I had ever hooked up with another girl, if we all "lezzied out together in the locker room". He literally would not stop.
So about three sips into my Moscow Mule, I made up some stupid lie and said I had to leave, and on the way home I posted an Insta story about what a Neanderthal nightmare this guy was. I guess he must have done some post-date internet stalking because he sent me about a dozen messages over the next three days telling me what a b*tch I was, that I was lucky he ever bothered with me at all, and that his suspicions of me being a lesbian had to be true because I’d rebuffed him. Dreamboat.
Bethan, 23
I have so many bad date stories it's ridiculous. But the best one was when I had a good date with a guy and he offered to walk me home. Once outside my house he told me that he had only come on the date to “see if he could get over someone” and proceeded to thank me for my time, saying that he “feels much better about himself now because he knows that he can easily date other women”. Couldn't he just have said “Nice meeting you” and then proceeded to ghost me? Because that would have been better than finding out I was just being used.
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Ava, 27
This American guy came over to my house with a bottle of rosé, and the date was totally going fine. Until we had sex. He only wanted to do it doggy style and we didn’t kiss once! But the cherry on top was when he had a look at some photos I had taken and said that “maybe if I tried really hard I could actually maybe do this for a living”, despite the fact that he’d only been taking photos for five months and I had told him I’d been working professionally as a photographer for 10 years and had a degree in it…
Ella, 24
I waited for this guy outside the Tube station for 45 minutes and when he arrived he was about four years older than he claimed and five stone heavier than his pictures. He talked about how his mum had passed away, which was really, really sad but a bit weird for a first date. He then mentioned cooking, and when I said I don’t cook he asked, “You can’t cook, or you won’t cook?” and I said it was a bit of both, to which he replied, “Well, you’re going to learn.” He then told me how he wanted to take me to his home country, and he really wanted to introduce me to his aunt (with whom he lived) and when I said no he thought I was being rude, even though I had known this guy for all of two hours. He then got really offended when I refused to have sex with him, but texted me the next day asking when we’d go out again…
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Lauren, 25
This story is actually quite tragic because it was the best date I had ever been on. What started as a coffee date turned into drinks, then dinner, then after-dinner drinks. When all the bars closed we sat on a park bench and talked all night, even had the most romantic kiss. He walked me home and we snogged outside my house for a bit. What I didn’t know was that he had just had a hernia removed from his testicles, and the kissing got him a little too… err… excited. So excited that one of his stitches burst! We had already made plans for a second date but he was so embarrassed I never heard from him again.
Barbara, 28
This was my first date with a guy who ended up being my boyfriend for five years. He asked me out for Valentine's Day which at the time (age 16) seemed really cute and not at all weird. We decided to go to dinner and then play mini golf. About halfway through dinner, he gets a phone call from his little sister who was spending the night at a friend's house but wanted to come home because she didn't feel well. So he left me at the restaurant and went to pick up his sister, therefore I decided to leave the restaurant and forget about the date. He then called me to apologise and said, "Let's go play mini golf but is it OK if my sister tags along?" Because I liked the guy, I decided to be nice and said yes. Things were going fine, then his sister ran over because she made a hole in one and about 10 seconds later, threw up on my shoes. He apologised and we all decided that it was time to go home separately. But the final thing he said: "I only have enough cash for me and my sister. Can you pay for yourself?"
To hear more *awks* first date stories from Maya Jama and Vanessa White, listen to the full podcast at freyalingerie.com/melons.
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