Stede Bonnet's love life is completely non-existent and an utter tragedy to behold - At least, according to those closest in his life.
Thus they're compelled to do what any group comprised of an ex-wife, co-workers turned friends through sheer proximity, and assorted significant others of aforementioned co-workers turned friends would do: Set up five blind dates that Stede Bonnet has no choice but to go on.
Stede keeps on showing up ridiculously early to these dates, but at least the bartender is friendly.