Several versions of their legend exist. By most accounts, Gilbert was a sailor (who may have served under the pirate Peter Easton). He and Sheila met when the vessel she was on was seized by Easton and his crew, or when Sheila was rescued from her pirate captors. Either way, they fell in love and chose to make Carbonear, Newfoundland their home.
Please keep in mind that the story of Gilbert and Sheila is folkore, rather than documented history. The now popular story was based on family tales from part of the Carbonear Pike family, but the true original story now seems lost to time. If any part of the legend is based upon real people, it seems unlikely that their names were Gilbert and Sheila since no evidence has yet been found to prove that such a couple existed. That said, I have begun collecting information regarding the story of Gilbert and Sheila, as their legend alone makes an interesting contribution to the folklore of Newfoundland.