It wasn't awkward at all in Jack's book. He was after all quite uniquely qualified to understand this sort of thing. The only thing that was awkward, really, was his resemblance to Malcolm Merlyn, and he was grateful that she seemed able to look past that to accept his comfort, at least for the moment.
"Yeah, I know," he said sympathetically, fishing out a clean white handkerchief as she moved away and offering it to her to mop her face. "It's a scary thing to have to face, and no-one's ever prepared for it. Do you know how far in your future it is?" There was no-one he recognised in that picture, to give him a clue as to relative dating.