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Three Dating Disasters: Lessons in Love

A few years back my friends convinced me to give online dating a spin; it had worked for some of them and I had been single for some time so I decided there was no harm in seeing what fish were in the online sea. Safe to say my first three dates were absolute disasters! Perhaps I rushed in too quickly, was overly keen to see who was out there or perhaps I just didn’t know what I was doing. Either way I learned something from each disaster, and I’d like to share that wisdom with you now.

The Princess

My first date and very probably my first big mistake, I thought ‘The Princess’ was absolutely stunning, and when she agreed to a date together I was so excited that I didn’t stop to think. It wasn’t long into the date when I realised we were from very different backgrounds and had very little in common. She was a privately schooled ‘Daddy’s girl’ and was upset from the beginning that I hadn’t selected a nicer (read: more expensive) restaurant. Needless to say we didn’t see eye to eye on many topics of conversations and her assertiveness was at times difficult to manage.

I learned several things with ‘The Princess’, firstly not to get caught up in people’s appearances (which I should have known already!) and secondly to spend a bit more time studying potential date’s profiles to avoid such a disastrous mismatch in the future!


The Intellectual

For the second date I followed my own advice and I contacted someone who I felt had a really interesting profile. This wonderful lady was a recently qualified lawyer, a keen reader and an aspiring philanthropist – she seemed utterly perfect. Unfortunately despite all her credentials and hobbies, ‘The Intellectual’ was a bit of a snob. We had some great conversations, but her unwillingness to enter into conversations about things she deemed ‘low-brow’ was infuriating. Worst of all she was so keen to talk about her own achievements, leaving me little chance of getting a word in edge ways!

In the end, although the date wasn’t as terrible as my first, it was clear that we weren’t a good match. I learnt another valuable lesson from ‘The Intellectual’ – you can never tell everything about a person from their profile. Even people that look like they’d be a great match on paper can lack chemistry in person.


The Liar

My third date began so promisingly, with a series of messages that spanned a whole week in the run up to the date itself. Our conversations were bristling with chemistry and a fantastic shared sense of humour (one of the qualities I find most attractive). When it came to date night I was so excited to meet the first person I’d felt I had a genuine connection with. This individual worked in the same industry as me, loved the theatre and music but also could appreciate a joke based on a terrible pun – I was in potential heaven. Unfortunately I learnt the hardest lesson of all with ‘The Liar’ – not everyone is 100% honest online. The tough part is that there was nothing particularly wrong with her; in fact she was quite lovely, but I couldn’t move past the fact that she had lied (or exaggerated) about certain things.

We did share a sense of humour, but she didn’t work in the same industry, she did enjoy the theatre, but she hadn’t actually seen half the shows she had claimed to have seen. It made the whole evening very confusing and at points awkward and in the end I couldn’t help but feel a bit let down. I reinforced in my mind the lesson of being honest, even at the earliest stages of a relationship; it’s a lesson I hope other people choose to follow.



Dating is a fantastic experience and the world of online dating is making it easier than ever to find potential partners. It’s not only a huge amount of fun, but also a great chance for some personal growth. There will be ups, and there will be downs; I can only assure you that the downs won’t be for nothing and will leave you a stronger, more resilient adventurer in the search for love.

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