In the pilot, Ward says to Coulson, "Is that who I think it is?" Ward had not met or worked with May before Coulson formed the team. Ward had heard stories about "The Cavalry" (as it seems everyone had). Except for Fitz and Simmons, no one else on the team knew each other previously.
I'm pretty sure that the end of The Well (episode 8) is supposed to be the first time May and Ward get together. The beginning of this episode makes it clear this has to be at least the 2nd time because Ward says something about doing the same thing as before - leave separately, stagger arrival times, etc. My thought was that this ep doesn't take place very long after the last one, so I'm not sure that they've hooked up a lot. It certainly seems possible this was only the 2nd time. And I think Ward said at the end of The Well that overnights aren't standard. I'm not sure I believe that they're hooking up on the plane.
Bottom line for me: I'm happy it isn't Ward and Skye getting together - at least not at this point. Everyone could see that coming from the pilot and I'm glad for the curveball.
