This guy couldn’t afford to split the bill on a first date. By date three he’d bought the restaurant.

Jack had been waiting for his date with Tonia for weeks. Asking girls out didn’t come naturally to him. He’d always been the shy kid who asked his mates to do it for him. But after a recent health scare Jack was in no mood to wait. He stuck his neck out, risked embarrassment and secured his prize.

On the day of the date Jack was anything but calm, and this had nothing to do with romantic nerves. He’d spent the past 48 hours chasing up clients for payment. As a freelance writer this sort of thing was a regular occurrence, but Jack was perilously close to his overdraft limit. Thankfully, the client promised that payment would be in his bank account by the middle of the day.

Satisfied he could afford to pay his way, Jack turned up to the date to meet his new paramour. Tonia looked fantastic, and the restaurant he’d chosen was the perfect setting for their first encounter. It was quaint, it had a reputation for great food, and it wasn’t too busy either. There had been rumours the place was about to close due to lack of business, but Jack always thought the only thing it lacked was decent publicity. Either way, if it was going to close, at least he’d managed to take Tonia here beforehand.

The date could not have gone any better. Tonia was great company, the meal was delicious, and a drinks date was planned once they’d settled the bill. Tonia was a headstrong, independent girl who insisted on splitting the check evenly. Jack agreed, but when he tried to pay his card was declined. The waiter smirked. Tonia was sympathetic, but Jack was livid. His client had lied to him. He’d ruined the first good date he’d had in years. Riddled with awkward thoughts, Jack felt as if a shadow had been cast over the entire evening. Tonia liked him a lot, but Jack couldn’t look her in the eye after what had happened.

A few days later Jack’s payment finally did come through, at which point he threatened to quit working with his client for good. After breaking down, rather unprofessionally on the phone to this client, he ended up divulging the story about his date and how his card was declined. On hearing this, the client, of course, felt terrible for being the reason for Jack’s embarrassment. He then offered Jack the job of a lifetime at his very large, thriving Marketing company.

Jack politely declined but after a few emails back and forth, he had an offer which he simply couldn’t turn down. He had a much higher basic salary plus commission on new clients. Jack knew he could bring his clients over from previous jobs he had done and he was right.

That next few weeks, he received his new salary, his commission payments AND all the backlog of payments from his previous job. He had a missed voicemail from the restaurant cancelling a table he had for the weekend due to closure. Then he had an idea.

By Friday of that week Jack had signed the papers and took Tonia there to celebrate. The meal was delicious as usual, and the waiter bent himself over backwards in an attempt to be more polite. As his new boss, Jack could’ve fired him, but he’s not that kinda guy. He knew how hard it was to pull down a job that pays so badly. The tip Jack left made it clear that there were no hard feelings on his part.

Jack and Tonia’s third date ended with a kiss and with Tonia insisting on going dutch, despite Jack owning the bloody restaurant! She’s a keeper for sure. As Tonia visited the bathroom, Jack sat back and contemplated what had happened to him of late. Jack was never a rich man. He couldn’t afford to go crazy. But his life had changed forever.

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