October might be too soon, it's best to offer this to a gentleman you've seen a few times.
I have another conundrum of sorts as well. I have tickets to a musical in October. I thought it would be nice to share with a gentlemen on a extended date. I wouldn't include the cost of tickets as that would be my treat, and yet I have no idea how I would offer this.
It's a nice idea though, I hope you attract clients who would appreciate the thought you're putting in this.