I used the online dating sites pretty heavily when I was younger and still single. (I'm married to a woman who I met via OKCupid, as a matter of fact.)
I think like many things in life, you only get out of it what you put into it. If you approach the sites with the "kid in a candy store" mentality (which MANY men and women do), it turns into a way to flip through hundreds of photos to pick out only the people you find the most physically attractive, and to see how many of them you can get to go out with you. A whole lot of people who really tried to leverage the power of the dating site to find you better matches gets squandered or trampled on by all the people "clicking the pretty pictures". (After all, why waste hours taking numerous personality profile tests, writing a complete "bio", etc. -- if all of it was ignored by the majority of people anyway?)
Realistically? I know I'm not a bad looking guy, but I'm not a "head turner" either. I think I rank somewhere solidly in the "average" category on looks. So if we're only competing on a selection of photos alone, I'm going to be consistently left in the dust by guys 10 years younger than me, guys who go to the gym at least 3-4 times a week, etc. That's fine with me though, because I wasn't looking to date models who walked right off of photo shoots either.
So what happened for me is that I actually had some of my most enjoyable dates with women I met on Craigslist personals -- where half the time, they didn't even share a photo. I just went by what they wrote and how they wrote it, to determine if they seemed intelligent, relatively honest, and if we had some things in common. None of these dates led to anything serious, but they felt "genuine". Both of us were going into it pretty much blindly, with "blank slates" as expectations. And even when there was no chemistry, we were able to walk away as friends who just enjoyed a really good dinner or a few games of billiards or what-not.
When I put in the effort to really read through detailed profiles, compare "compatibility percentages" based on tests we both took, and contact people who shared mutual interests and beliefs over on sites like OKCupid? I generally got no response at all. I really think most women on there were just overwhelmed with a large number of initial contacts from all the guys who just said, "Ooh.... sexy photo. I'm gonna chat her up!", and/or got sucked into behaving the same way on the site.
When I finally met the woman I married, it was only because I'd already given up using the web site and left my profile sitting out there for months. I got an email notification that she had sent me a "Woo!", so I signed back in to see who did it and what their story was. That's when it turned out she lived in a different state, but had gotten so frustrated by the lack of communications with people taking the site seriously that she kept expanding her search outside her city and eventually to other states. She liked what I had to say in my profile, so sent me the "Woo" rather than wasting time writing a big letter for nothing (like had so often happened to her previously).
Tindr wasn't even a "thing" yet back then, but when I read about it as a new dating app, I realized it captured the essence of how most people were really using all of these other sites to begin with. Why bother taking quizzes or writing a lot of content? Just show the sexy photos and let people hit on each other....
Attaching THAT to a personal assistant is going to be relatively pointless, IMO. But a site that makes a serious effort to collect user info and preferences, that actually gets USED by serious individuals who want to fill all of that out? That could work.