I really don’t think they will.. That scene on the bridge in episode 8 really felt like a goodbye. The creators of Black sails have alluded to max turning into a much darker character next season so we shall see where that goes. But I really feel like their relationship has run its course and there needs to be a new romantic interest.
It’s our sailing time.
Black Sails - 1x08 - Eleanor Guthrie
"Told you I was certain about my information regarding the Urca; unfortunately, you and I failed to take into account the weather.
The Urca de Lima wrecked at sea last night, dashed by the storm.”