| Darrin the Bold | |
 | |
| First Appearance: | A Most Unusual Wood Nymph |
| Last Appearance: | The Return of Darrin the Bold |
| Portrayer: | Dick York Dick Sargent |
| Species: | Mortal Warlock (temporarily) |
| Occupation: | Feudal Lord |
| Family: | Darrin Stephens (descendant) Frank Stephens (descendant) Tabitha Stephens (descendant) Adam Stephens (descendant) |
| Significant Other(s): | Serena (dalliance) |
| Residence: | Castle in Ireland (fourteenth century) |
Darrin the Bold is the ancestor of Darrin Stephens. In the fourteenth century, he kills Rufus the Red. In retaliation, a wood nymph, Gerry O'Toole (who is Rufus the Red's true love) places a curse on Darrin the Bold and all of his descendants. The curse is lifted after Samantha time-travels into the past to undo the deed.
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