Fortunately, he met the "love of his life" just a few short months.
However, his membership was automatically renewed without his knowledge.
He was taken aback to learn that a debt collection organization was trying to get £358 from him.
The events in Simon's life are hardly unique. The Citizens Advice Bureau (CAB) reports that each year, hundreds of millions of pounds are wasted on subscriptions that go unused. The majority of respondents in a recent survey placed the blame on automatic renewal.
It's easy to get into the "subscription trap" and end up paying for services you don't need after signing up for a free trial and forgetting to unsubscribe.
The government of the United Kingdom is moving in the direction of restricting the methods used by major internet shops to try to lock consumers into subscriptions.
It proposes new regulations that would oblige businesses to notify their subscribers via "reminder notices" whenever their subscriptions lapse.
The proposed changes have not been welcomed by all. Disney said that the government was trying to "micro-manage" the business practices of subscription streaming services.
Companies in the United States have been warned by regulators that some practices, such as hiding auto enrollment letters, are illegal under US consumer law.
This month, Amazon became the most visible target in that struggle when the United States sued it over allegations that it deceived customers into signing up for automatically renewing Prime subscriptions and made cancellation difficult.
For 18 months, I shelled out just $6.99.
There is a rising market for subscription services, which are offered by an increasing number of companies. A lot of them give away freebies or discount coupons if you sign up.
However, according to the BBC's interviews, some subscribers feel trapped after forgetting to discontinue their service at the end of the free trial period.
John, for instance, told the BBC that he had forgotten to terminate his 30-day free trial of Amazon Prime Video, even though he had already started paying for the service.
I'm really disappointed that I wasted £6.99 per month for 18 months.
A profitable business strategy
Claire Holubowskyj, a research analyst at Enders Analysis, argues that automatic enrollment is a no-brainer for large corporations like Amazon.
She argues that corporations can increase their customer base through either continual investment in product improvement or through subscription, the latter of which is a "easier route."
After a single purchase, customers are committed to continuing to use the product, guaranteeing recurring revenue at little to no extra cost to the business.
According to Ms. Holubowskyj, there has been a change in the consumer mentality in recent years, and as a result, we have become accustomed to making monthly payments for goods and services. "It's the standard practice now, and there's a lot of value for customers, especially with technological software, where updates are typically included in the price."
However, if a subscription model provides clients with freebies or discounts, then it's not all negative for them, and many businesses do send renewal reminders.
"ensure consumers get a fair deal," according to the UK government, is the goal of the proposed Digital Markets, Competition and Consumers Bill.
However, Citizens Advice argues that it should go even further, suggesting that companies be required to have customers actively opt in to continued service after a free trial period ends.
Consumers' wallets are under stress, and the government must recognize that. Executive director of policy and advocacy Matthew Upton said, "This has to be the beginning of reforms, not the end."
John says he appreciates efforts to make it more difficult to be automatically renewed into a subscription, but he is concerned that he will fall into the trap once more.
"It was such a trying experience; I'm still very anxious about it. It's absurd; these businesses put profits before people.