In today’s challenging healthcare market, affiliation can be a wise strategy. However, it should not be entered into lightly, and old assumptions and critical success factors do not necessarily apply. Explore conventional wisdom about healthcare affiliations, identifying those aspects that still apply and those that must be debunked in light of current environmental circumstances. Attention will be paid to all phases of the affiliation planning process, including making the initial decision to “take the plunge,” finding a lifelong partner, creating a strong foundation for a lasting marriage, and starting off on the right foot after the honeymoon.