throwaway_abc
The answer that I came up with: the company will charge less each failed date. This way, after a certain amount of dates, they will theoretically lose money by having you as a customer. This incentivizes them to get you a good match before then. On the flip side, the initial price should be high enough such that it is in the users interest to see if it will work out rather then giving up easily. Lastly, if the previous date request is months before the current one, the company can say that the previous date was a success and start over.
The only problem that I dont know how to deal with is the user whose goal isnt to get a date, but to harm the company. My guess is that some sort of feedback from the dates can asses whether or not this is indeed happening.
It should be your choice. If you choose not to go on a date, thats on you, the dating ring's work has been done. If, however, you accept the date and they dont, there is nothing you could have done and should be set up with someone else. From the dating ring's perspective, that should be fine too because work was done for value (i.e. the party that declined the date got their value). This also goes well with your second statement.