A cottage industry is springing up around the web that does make one think hard about whether the solution lies this way. There are dating coaches; like other kinds of life coach, they offer training in how to date. They train you in the finer points of flirting, fashion, communication, self-esteem, evolutionary biology, psychology, dancing, and so on. We'd rather link to the Wiki on this one than any particular date coaching service, for fear of appearing like an endorsement.
But the concept of a dating coach is not that new at all. It goes all the way back to 1897, at least, with the play by Edmond Rostand. Cyrano helps his friend Christian win the heart of Roxane, using his own wit and charming words to be spoken through Christian's handsome face. While in this case, Cyrano is secretly in love with the lady himself and so is not doing it for money, the principle is the same.
It makes sense that life coaches would specialize in this department and there would be a market for them. Who among us hasn't asked another's advice in matters of love? We ordinarily turn to our friends and acquaintances for anything from "Should I wear these shoes?" to "Does he really like me?" A dating coach makes sense in that regard - why not ask an expert?
Yet we can also see where the stigma comes from. There is controversy over this practice, where it's associated with the "speed-seduction" subculture. This isn't necessarily anything like that, though. Done right, it can be a solution for people who are desperately lacking in social skills in an increasingly digital society where nobody has the time to really study people anymore.