The Love Diaries: “The 14 Weird, Wonderful and Disastrous Dates I Went on Before I Found ‘The One'”

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].

This week we hear from Anna* who chronicles three years of dating.

I had always been someone who went from one long monogamous relationship to the next. But, in my early 30s I suddenly felt like the dating world had changed. For a start, there were now five thousand apps and the days of just striking up a flirty conversation in a bar seemed over – now it was all about spending evenings scrolling through profiles and making split-second decisions as to whether to swipe left or right.

I found the apps exhausting and exhilarating over the three years I spent (on and off) on the apps. Here’s a snap shot of who I dated – from the ones who I lasted on a date with for mere minutes, to others that lasted for months (but clearly shouldn’t have!).


He ordered a very complicated cocktail, I got a gin & tonic and he asked if I “always played it safe?” Not a great start. The entire date was awful, so I said I was meeting a girlfriend for dinner. He asked if he could come too – then tried to kiss me as we left. Neither of us messaged each other again.


We had SO much great banter on line, I couldn’t wait to meet him. Except, he was going on a work trip and when he got back, I had the flu. For three glorious weeks we messaged and text each other furiously, with witty, flirty messages. Finally, we set a date, and…. it was a disaster. There was somehow zero chemistry and we could barely say a word to each other. I wondered if perhaps we were both just nervous after the lead-up, and I never got the chance to figure it out because he never replied to my messages.


Ken was approximately 15 years older than his profile and when I tried to mention this he acted shocked that Tinder must have changed his age somehow. I left as soon as I finished my chai latte.


Mike was twelve times more handsome in person and next thing I knew, I’d had three rosès and spent an hour making out with him – very publicly – at my local pub. I thought we’d had the best date of our lives – then he ghosted me. Heartbroken. Plus, I couldn’t go back to my local for quite some time.


Jacob was hilarious over messages but I couldn’t tell from his pics if I’d feel romantic about him and was gun shy from the Tony experience, but I agreed to meet up. He was hilarious in person – and smart and kind and everything you look for. We went for two more dates and had the best time but, bizarrely, I felt nothing – even after he kissed me good night. I decided to give it one more go but couldn’t manufacture feelings. I asked him if we could just be mates and he said he was so mortified he didn’t know what to say. We haven’t been able to make it as friends.


Two hours into my date with Pete I realised that he hadn’t asked me a single thing about myself – we had (or rather HE had) only spoken about himself. An hour later, nothing had changed so when he messaged the next day to say we should do it again I sad thanks, but no thanks. 


David was super tall, dark, funny, and confident. Within moments of matching he sent messages and we arranged a date at his local the next afternoon. One date led to another and before I knew it we were regularly seeing each other and things seemed easy… until… two months later I met a friend at his local for a drink… and David was there on another Tinder date. Goodbye David.


Paul was fun and gorgeous, but… not the brightest bulb. But still, we kept going on dates (because, fun and gorgeous!), until he said to me one night that he didn’t think I was emotionally available and our relationship wasn’t progressing because of it.


Alan was a friend of a friend who thought that we would be perfect together, so I agreed to meet up. Interestingly, Alan suggested we meet for breakfast before work one day. He just happened to suggest my favourite place, so despite having some hesitance about the whole thing, I started to wonder if I was being a little harsh. But then we sat down and things right away felt awkward. I was ready to order food, but he just wanted a coffee, so I did the same and made a mental note that I would need to leave early to pick up something to eat on my way to work! And then… the conversation just felt stilted and awkward and weird and he talked a lot about his new job. He probably thought it was a good way to impress me, but instead he just came off arrogant. Feeling like it had been a bit of a waste of time, we said goodbye, stepped out onto the street and he went in for a hug, then awkwardly tried to go in for a big open-mouthed kiss, on the busy street, at 8.30am, after a mediocre date. I declined a second date.


Matt looked super familiar and then I realised we went to university together. Why didn’t I spend more time with him back then? Matt was funny, smart and easy to hang out with… until,  three months later he called it quits. How come? He said he had been “holding back in the bedroom” and was actually super into role-play, being dominated, whips, S&M and didn’t think we’d be compatible in that way… I wished we’d had this conversation MONTHS earlier.


About 10 minutes into the date, he described Jacinda Ardern as “not his Prime Minister” and had the gall to call her “Cindy” and from then on, everything he said sounded twinged with misogyny. Couldn’t get out of there fast enough. 


Michael and I had great banter, so I started getting my hopes up, particularly when he suggested we meet up AND the place just happened to be one of my favourites. Then he casually asked, “Hey, how tall are you?” and I told him, to which he replied, “Oh sweet, I’m 6 foot so that’s perfect.” However, upon meeting Michael – in flat shoes,  I must add – it became very clear that he was not six foot. This didn’t bother me in the slightest, but it did bother me how much it clearly affected him. Soon into the date he asked me if I always wore high heels and I pointed his attention to my ballet flats, which is when he accused ME of lying about my height. “There’s no way you’re 5’9” if you’re nearly my height and I’m 6 foot!” he said. I was clearly taller than Michael and he was clearly smaller than 6 foot. “Is this a problem to you?” I asked, to which he said he “didn’t like liars”. I went to the bathroom but instead paid for my drink and left the bar.


Tom was a busy guy, with a busy job and children he had joint custody of – in fact, it hadn’t been too long since he and his former wife had split. He said that in reality the marriage had been over a lot longer though and he felt like they’d split – mentally – years earlier. Things were obviously tricky while he learned to navigate the new co-parenting situation, so I gave him A LOT of leeway and tried to be understanding about meeting up at slightly odd times. This turned out to be a massive mistake, when five months later I learned that part of what was making him SO busy was that he had another girlfriend too. FFS.


Luke was definitely not my type. For a start, he was much younger than guys I normally date and he was American and was only going to be in NZ for a little while. BUT he turned out to be the best palette cleanser imaginable. He had that Southern charm and called me Ma’am at times, opened doors, bought me flowers and hung on my every word. Maybe because I knew it had an expiry date on it, the whole thing was much more exciting and perfect than it would otherwise have been, but it was EXACTLY what I needed.

Want to share YOUR dating diary? Send your story to [email protected]

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