Jacob Macalister attempts to earn his way through college by guiding young men and women through the dangerous world of dating and relationships. He starts by estimating the chances of a girl accepting an offer of a date by a guy. In the process, he enters the realm of romances and relationships. Some relationships, he is paid to salvage, though it may be impossible. Other relationships, he tries to redefine or let the person down easy, if such a thing is possible.

All the while, he is seeking a plain but virtuous girl to call his own.