The law relating to “offer” and “acceptance” is seemingly simple when it comes to stating it, but less than straightforward when it comes to applying. The reasoning in this area of law is artificial, contrived and “backwards.” Rather than deductively applying the definitions of “offer” and “acceptance” to real world scenarios, courts seem to be deciding cases first by deliberating upon a host of considerations specific to the domain in which the case arises—and seem to stick the labels “offer” and “acceptance” on to the fruits of these deliberations afterwards. This article seeks to give heuristic short-cuts to anticipate a common law judge’s approach to “offer” and “acceptance” cases by focussing on the “tacit knowledge” used by lawyers to negotiate questions arising around these issues. It also seeks to get to the heart of why applying “rules” in this area yields poor results.