Thank you for creating something and trying to help people in one of life's most important activities. I want you to know that everything after this is coming from a place of genuine respect and support. My preemptive apologies for being blunt.
"The two of us had that sinking feeling in our early 20s that we’d missed our best opportunity to date," is a bad sign.
First, you were in your early 20's! Grow, learn, break a heart, get your heart broken, travel, read, get fired, start a nonprofit, experience life. Why were you so caught up in finding your optimal date while some of the best (i.e. most painful) growth opportunities were passing you by? I am not sure you have the perspective or life experience to be counseling people on something like dating.
Second, dating is not a game you can "win." One of my favorite professors ever, a statistics genius with possibly a touch of Aspergers, explained to our class one time how dating is like science. A "failed" experiment is knowledge gained about the world! A "failed" relationship is a chance to learn about yourself, others and relationships. The only way is to try.
Third, this is creating an arms race of banter instead of allowing people to genuinely connect. There's a famous OK Cupid article demonstrating why being your most authentic self is actually beneficial to your dating life (https://theblog.okcupid.com/the-mathematics-of-beauty-51bd25...).
There are a number of other reasons I think this is not a good way to spend your time, as a business, as a life pursuit and as a thing that detracts from the world, but I'll stop here so I don't sound like a complete jerk. I would strongly urge you to reconsider. Mostly, I think you just need time. Again, kudos on making a thing.