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5 Important Lessons I Learned From My Worst Date Ever

Courtesy of Funny or Die
Courtesy of Funny or Die

Rushing from the cab into the inner city bar we’d arranged to meet at, I quietly cursed myself for not having planned ahead more and arrived on time. My tights had snagged, my door keys snuggled out of sight between the sofa cushions and a spring rain downpour had made a warm afternoon into a curly-haired girls nightmare. Oh well, I’d made it. Soon I’d be small-talking my way into forgetting it all anyhow…

It seemed I was first to get here after all. So I sat down and ordered myself a Spritz and waited for my date to arrive. And then I waited. And I waited. And an hour later I wondered why I’d waited at all. You see, when my date arrived he wasn’t what I expected.

His profile said 30 but he was visibly pushing 40. The thick hair of his profile photo was replaced by balding and tufting. ‘Smart is the new sexy’, I’d thought when I read the words ‘Mechanical Engineer’ in his profile, but after some awkward introductions I’d found he was in fact unemployed. None of these facts were sinful in isolation but the fibbing left me cold.

Thirty minutes later, over the noise of a now busy bar, I could hardly hear my date speak at all. Not that he seemed to have anything left to say. So, unable to hear my own voice, I became nervous and defaulted to the first subject that came to mind: Cats. ‘Oh God yeah, I love cats. Let me see… my first cat ever was called Jasper…’ It didn’t last much longer after that.

So there you have it, no one died, there were no false-teeth or embarrassing invitations to part-take in strange sexual practices, but it was dull and somehow so much worse. As we left with no plans to meet again, I wondered – ‘What went wrong here? Was this his fault… or mine? What could I learn from this?’

  1. A little planning doesn’t hurt
    Everything that made me late was actually of my own making. If I’d put my keys somewhere safe, booked a cab in advance and packaged a spare pair of tights I wouldn’t have had to rush myself, making me feel even more pressured. If I’d been tasked with planning this date again I would pick a different venue too as in the daylight, this trendy urban bar was actually a bit of a dive.
  2. There’s really no such thing as ‘fashionably on time’
    Whether you’re late or he’s late, it’s not ‘cute’, ‘teasing’ and it doesn’t show that you’re ‘in demand’, it’s just tedious. We all end up late sometimes but just like you wouldn’t be late for a job interview you shouldn’t be late for this.
  3. Don’t feel you have to fill every silence
    While it really is a good idea to have a few conversation starters in mind, such as ‘what do you like doing in your spare time?’ a complete breakdown in conversation probably means there might be a lack of chemistry. If your date does nothing to help you keep a healthy flow of conversation, then don’t feel obliged to either.
  4. Keep your profile up to date
    Hopefully it goes without saying but an online dating profile should show who you are right now, not who you were ‘at your best’. I’m as bad as anyone for this, but a new profile photo helps you find each other in a crowd and avoid uncomfortable scenarios. And admit it, you need to actually be attracted to your date!
  5. You can’t win them all
    Sometimes it’s not really necessary to work out the what if’s and buts, but simply to accept a bad date for what it is. If we were meant to have great chemistry with everyone we’d never find monogamy. And yes, I’d learnt more about what I don’t want than what I do, but also how I can make sure I’m the best me for someone else also. Here's hoping my next date goes a little smoother as a result!

Find more dating tips and follow my adventures at my toyboy and cougar dating blog.

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Lucy is a member of Team Toyboy Warehouse. She’s on a mission to challenge old and obselete views about dating and empower people to go after what they really want. Check out more blogs from her about dating at www.toyboywarehouse.com

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