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The first time Jack kissed the Doctor, neither one really realized it.
It had been an awful day. When they got back to the TARDIS, Jack was asleep on his feet.
The Doctor was carrying Rose. Before he took her to her room, he firmly instructed Jack to get a shower and go to bed.
The little kiss the Captain pressed to his cheek, too exhausted to express his gratitude in words, didn't even register with him.
Until the next night, when Jack went to bed with just his usual cheerful "g'night," and the Doctor felt a pang of loss.
The first time Rose kissed Jack was on a dare. Jack had been teasing her about her repressed century, and she pressed her lips to his simply to prove him wrong. She thought she'd shock him by running her tongue over his lips, but his response made her the one to yelp.
Jack apologized, as did she. The Doctor just shook his head, grumbling about stupid apes not realizing the vastness of cultural progress three millennia could bring.
The first time the Doctor kissed Rose, it was to comfort her when she thought herself too old-fashioned and backwards for them.
The first time Rose kissed the Doctor, and the first time Jack kissed Rose, none of them remember. Probably late some night, curled up on the couch, between mugs of hot chocolate and silly movies.
But Jack will always cherish the memory of the first time the Doctor kissed him. Rose had gone to bed; Jack was sitting in the library by himself, drinking too much hypervodka and thinking about Gray.
A cold hand taking the bottle, a firm kiss on his lips, and a chiding "Bed, Captain. Now."
Funny how little it can take to make one feel loved.