Two months after our only date, he asked me to pay him back

My friends and I still laugh to this day about the worst date I’ve ever been on. 

In 2017, I was about to turn 50 and had recently become single for the first time in my adult life. The idea of trying to meet someone new was as exhilarating as it was scary. 

And so I decided to get back into the dating saddle – through apps. I felt the highs that came with casual flirtation, swiping left and right, and the trepidation when it came to meeting someone for a first date and working out how I felt being let down or indeed letting others down. 

I’d been on a few dates by the time I met Simon* and I was seriously feeling back in the real world. I had enjoyed walks on the bach, coffee dates and one or two evenings out for dinner. 

I was drawn to Simon’s profile as he looked to have an active social life; his photos showed him with friends having dinner, on a boat dressed in casual wear and I just felt that he might be an interesting person to know.

When chatting, he appeared to be a lovely, kind man, so when he popped the ‘shall we meet’ question after a few weeks, I felt butterflies in my stomach. 

He’d been so funny and pleasant, I immediately agreed and we set the date at a fish restaurant in town I’d been wanting to try. 

But when I arrived, he wasn’t quite what I expected. He was really quite slim and shorter than I imagined. While not immediately my physical type, that didn’t get in the way and I was still open to getting to know him. 

Over dinner, we talked about our work, about what plans we had for the summer holidays – the usual kind of small talk of getting to know a stranger. 

I’d hoped that he would ask me about me a little more, however, as he clearly liked to talk a lot about himself. 

As the evening progressed, I realised that we had very little in common other than that we both enjoyed seafood.

There was nothing particularly wrong about the date – it was just mediocre at best. I would compare it to feeling like I was taking a client or new member of staff out for dinner.

When the bill came, Simon reached out and picked it up, proudly declaring that he would pay for dinner. 

I left a note with the money saying ‘No wonder you’re single’

Normally, as a lady of a certain age with somewhat traditional values, I would have let him. But, with my new independent lifestyle, I had been offering to go Dutch on all my dates. Especially as I knew this man was not for me, I said I would pay half. 

Still, full of bravado, Simon insisted. 

‘I am a gentleman and I won’t hear of you paying for the meal. I invited you to dinner and if you paid it would be an insult to me’, he continued. 

So I relented, graciously. As he walked me to my car I prayed he didn’t ask to see me again – I really didn’t want to say no under the circumstances – and mercifully he didn’t. 

As I closed the door, gave him a quick wave, and pulled away, I felt relieved that I could draw a line under that unsuccessful date. 

But it became clear the next morning when I received a ‘good morning’ text from him that he clearly felt the night went better than it did. 

My stomach sank when he offered a time and place for a potential second date. 

As gently as I could, I thanked him for a lovely evening and a delicious meal but said I didn’t feel that we had a great deal in common, so there wouldn’t be a second date. 

‘Why?’, Simon replied after a brief period of silence. 

I politely reiterated that I sadly felt we weren’t compatible and that I was at an age where I didn’t want to waste his time or mine. 

To that, he wished me well – and me to him – and he appeared to accept it. 

Or so I thought. 

Two months later, completely out of the blue, I received a message from Simon saying he had been thinking about me and asking whether I would reconsider a second date. 

I was shocked to hear from him after all this time, it wasn’t expected at all. 

I declined his kind offer and wished him all the very best. Nothing could have prepared me for his reply. 

‘Then I think you should pay for your half of the meal that we had, as that is only fair’. 

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I had an allergic reaction and threw up while totally nude on my worst date

I was completely taken aback and asked if he was joking, to which he said completely seriously that he felt duped into paying as he thought we were entering into a relationship. 

I was initially shocked; I re-read the message and then found myself laughing. I relayed the message to a friend and she was more horrified and annoyed by it than I.

Still stunned, I told him I had left the full amount of the bill of £80 with my security office at work for him to collect. My friend said it was a disgrace and told me not to do it but I felt that ignoring him may meant he kept messaging or being annoying.

Incredibly, he came and collected the money, hopefully seeing the note I left with the money saying ‘No wonder you’re single.’ 

Thankfully, after that, I never heard from him again. Sometimes I still can’t believe it even happened. 

But that’s just one of the pitfalls of dating later in life – my advice for those doing the same as me is to always know your worth and be responsible for yourself.

Oh, and always go Dutch!

So, How Did It Go?

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