Tag to Season 2 episode 1, "Shadows".
In retrospect, he should have known it was going to be anything but easy. Not the getting back into fighting form, if he flattered himself when he said his skills hadn't atrophied in his confinement, it wasn't by much. Besides, he had a lot of free time on his hands these days. There were worse ways to spend it.
No, it was reminding Skye she could trust him that was difficult. In fairness, he'd played his part as a HYDRA mole very, very well, and he knew he'd scared her after Providence. He'd miscalculated, and he regretted it. "Once burned, twice shy," wasn't that how the saying went?
When she finally appeared, Grant was ready. Sort of. He'd underestimated the effect speaking with her would have on him, the swoop of his stomach and the tightness in his chest. Oh, she was all business, but Grant made a point of the social niceties, of promising his loyalty and all the truths he possessed. Skye cut him off more than once, but she seemed to need the information on Creel and HYDRA communications in a hurry, and Coulson was almost certainly watching. That was fine - Grant had plenty of information tucked away inside his head, and throwing Coulson a bone for opportunities to talk to Skye? An easy choice.
He wasn't sorry for having withheld the information about her father until now. She wasn't interested in what he had to say, and he couldn't make her listen. He was just going to have to convince her. Anyway, as desperate as she was to learn where she'd come from, he'd been sitting on it thus far. A few extra days wouldn't hurt.
There were questions he anticipated. "How do you know this" was relatively straight-forward, but "why didn't you tell me" would be trickier. The rawest, ugliest truth is that it wasn't important to him before - up until Garrett's death, that was where Grant's loyalties had been. Garrett didn't feel like Skye needed that information, so Grant didn't pass what little he knew over. (Whether Garrett even knew he had the pieces Skye needed was a separate question entirely. Grant suspected not, Coulson played Skye's past pretty close to the vest, but then again Garrett had other things on his mind so he might not have cared.)
Obviously that wasn't an answer he could give to Skye. He'd have to think on it, now that he'd seen her again, figure out the best way to phrase it so it wouldn't cause her pain. He'd promised to protect her. That included protecting her from distressing news.
XxXxXxXxXxXxXxXxXx
Arms folded, Coulson watched Skye walk away from the freshly blanked wall of Ward's cell. Sighing he turned to May. "She's not happy with me for sending her down there."
May snorted. "Did you expect her to be?"
"No, not really."
"Well then."
Coulson straightened. "All things considered, I think it went relatively well. Let's hope we don't have to do that again for a while."
"You don't really think we'll be that lucky, do you."
"Nope. But I can always hope." May hummed and turned to walk away. "Hey," Coulson said. "I know you don't like it either, but we don't have a whole lot of options."
"I don't disagree, but I don't think that this is the best way to go about it."
"I know. Check on her for me?"
"Of course."