The Love Diaries: ‘I Squashed A Decade of Dating Into Two Years and 11 Dates’

Welcome to our series, The Love Diaries – a space for you to share your experiences, advice, fairy-tale endings, setbacks and heartbreaks. We’ll be hearing from industry experts giving practical advice alongside Capsule readers (You!) sharing your firsthand experiences with love – everything from finding love, to keeping love, to losing love.

If you have a topic you’d like to discuss, share your thoughts, experience or advice about, drop a line to [email protected] with ‘Love’ in the subject line. All stories that are published will will a Dermalogica BioLumin-C Moisturiser, valued at $119!

Today, we hear from Jane* who was single for almost all of her 20s and decided to join the dating apps in her early 30s.

I went on a first date with a man who had long, beautiful hair and a long, beautiful beard, so obviously I nicknamed him Hagrid. We had one wine, no food and a three hour date. I was so hungry while I was driving home, I somehow accidentally drove my company car into the wall of the KFC Drive-through. The orange paint scraped along the side was a dead giveaway and, mortifyingly, I had to sketch it out on a workplace health and safety form the next day. Oh and I never heard from him again.

The first Tinder date I ever went on was with a man who was the worst kisser I ever experienced and I say this with learned experience, because I made out with him for two hours in the hopes it would improve. Naturally, he still ghosted me but he clearly lives close to my CBD flat, because I see him and his girlfriend at our local supermarket all the time, always when I am on day one of my period and dressed as such. Still, I hope she likes a wet mouth.

“He once texted me, ‘thanks for sending me such a sexy pic of your tits’, which is a great text to receive from your boyfriend when you haven’t sent him a naked photo.”

Neil was handsome, British and an A-Grade terrible boyfriend, but I was so distracted by the first two factors it took me a long time to realise the third. We would date for a year, off and on, in which he would cheat on me so blatantly that he once texted me, ‘thanks for sending me such a sexy pic of your tits’, which is a great text to receive from your boyfriend when you haven’t sent him a naked photo. It’s even more embarrassing to admit that he still ended up breaking up with me, only to keep texting me for years afterwards until I finally saw the light (a therapist) and blocked him on every imaginable form of contact.

Great text chat over a dating app leads to some of the most surreal dates of my life, with a man who was more of a strange collection of facts than he was an actual human being. His sister made capes for a living, and when I met her, not only was she wearing a cape but also a velvet shower cap. I think they must have been trust-fund babies because they did not exist in the real world. He had a tattoo of a banana peel on his arm. He once ‘accidentally ended up living in China’ without realising how. And for his art degree, he recorded an entire album of covers by singing them as different barnyard animals; notably, Islands In The Stream as sung by a pig.

After meeting a handsome youth in a bar and dating him for a while, he ended it with me because he had ‘met a nice girl from church.’ Turns out, he was very religious which was a real surprise to hear after six months of dating him, I’ll tell you.

I went on a date with a guy from a dating app who had been an absolute delight over chatting and then, in person, proceeded to lecture for two hours about how I ‘didn’t know enough about opera.’ Okay… I’m sorry?!

Two weeks later, he broke up with me for ‘not living up to his expectations.’

Simon worked at my local library (classic rom com material! Hurrah!) and spent the entire date talking about the Dewey Decimal system, which is an interesting thing to talk about in this, the age of computers. There wasn’t much of a spark but it did make things slightly awkward when I then went to request books and realised there were so many self-help/mental health books under my hiring history 🙁

I reunited with an old friend from my early 20s who had been open about having a crush on me for years, only our timing had never worked out. Both single in our early 30s, we decided to give it a go and he wrote a long message on my mother’s Instagram post of me holding a ceramic turkey (!) about how happy he was we had a second chance at love. Two weeks later, he broke up with me for ‘not living up to his expectations.’ See ya, Steve!

We had one of those dream first dates where you talk for three straight hours and then when he dropped me home, we made plans for the next date. There had been a lot of funny horse-related jokes made throughout the night because he was flatting near a race course and I attempted to carry that on the next day. Banter!! Instead, I managed to send a text that read, somehow, that I was implying he wanted to have sex with a horse. (Well, that’s definitely how HE read it, even though it was truly not my intention). I showed my male flatmates our communication and they agreed I was never going to hear from him again. Which I didn’t. (Maybe the joke was a little too close to home??)

Once I dated a guy who insisted we watch Saw on our second date and then broke up with me the week after, which was very cool because I had Saw-related nightmares for months and absolutely no good memories to balance them out with. Still, that was a red flag I should have paid attention to.

We dated the first time we matched on a dating app, it didn’t work out and we both moved on. When we matched again a year later after both being back on the dating apps (always a humbling process), we went for a very long, four-hour date where we had absolutely no sexual chemistry but instead had very open and candid chats about how hard dating was and how we just wanted to settle down with someone we loved. It was a very lovely ‘date’ which confirmed that dating is a highs and lows process for everyone, no matter who you are or what stage of life you’re at. It can be easy to be cynical about men when you’re a single woman (see above) but, really, everyone has a bad track record until they don’t. And dating really is the best way to figure out what works for you (and what really, really doesn’t).

Want more dating stories? Check out ‘The 14 Weird, Wonderful & Disastrous Dates I Went On Before I Found ‘The One’

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