So what would work well?
The most intelligent way to date would be to have a matchmaker, a yenta. She would meet in person every man and woman she introduced. Men and women would be placed into two categories: paying clients and those who simply want to be put into her database. She would introduce paying clients to other paying clients and paying clients to non-paying clients. The only introductions she would not make are non-paying clients to non-paying clients (otherwise, how could she make any money?). She would carefully weed out those who are rude, flaky, ridiculously picky, not serious about wanting a relationship, clueless about how to pursue a relationship, emotionally unavailable, don't know what they want, or who don't follow through. She would insist that all clients abide by a code of conduct as to manners and that every client follow through quickly. (One such service in LA requires the men and the woman to call each other within 24 hours of being introduced.) Those that did not abide by this code of conduct would be dropped.
She would ask penetrating questions to determine what you really want and then introduce you to a few guys. After the first date, she would get detailed feedback from you as to what you liked and didn't like, thereby allowing her to more carefully calibrate whom she introduces you to next. She would get feedback from the guys, so that if you're making the same mistake over and over, she would coach you. ("Samantha, don't ever wear that green dress on a first date again, every guy hates it.") As your relationship with a guy develops, if there are obstacles the two of you are facing, she could serve as a sounding board.
The only problem with this approach is that it would be expensive. To do it right would cost about $5,000 per paying client per year, since there would be so many non-paying clients. Those who could not afford that, however, could always be non-paying clients, willing to be introduced to paying clients.
The key is that the matchmaker really does introduce paying clients to non-paying clients. Otherwise, the paying clients are getting taken, because there will always be 100 times more non-paying clients than paying clients.
Aren't there such services like that already available in Boston?
There is one service that advertises itself as catering to the high end which runs very good ads. From what I've heard, they don't deliver. They charge a lot of money and claim they will introduce you to anyone they know who they think will be suitable (whether or not they are a paying client), when in reality if they meet someone who is not a paying client, they focus on converting that person to being a paying client rather than introducing that person to their paying clients. In a typical year they might introduce you to 6 or so people, none of whom will be more of a "bulls eye" than someone you might meet off Match.Com.
I have heard that in New York and Los Angeles there are such services that do it right, such as Samantha's Table (on which the current TV show, "Miss Match," is based). (The Sunday New York Times had an article on these kinds of services. See "The New Arranged Marriage" by Melanie Thenstro, February 13, 2005, p. 34.)
So what about starting such a service in Boston?
I've met two people who wanted to start a dating service and I told both of them about my idea. Neither one has any entrepreneurial drive, as far as I could tell, and starting a business is always challenging at best. I question whether Boston is large enough to support such a service, since there are only so many people that can afford the fees necessary to run such a service properly. But if you're interested, give me a call. I'd be willing to be the strategic brains behind such a business, but I don't want to run such a business.