The First time he had attempted to tell Q was shortly after they had met. Bond found his attitude attractive, as well as his intelligence and body. Not that he could see much of his body in the coat he was wearing. James wanted to tell Q before he went to Skyfall, but nerves got the better of him. He thought that maybe he was still too in love with Vesper to say it to Q. But he immediately shook that idea from his head; he was well and truly over Vesper. Perhaps he was just afraid, since the last person he had loved betrayed him, and as a result, committed suicide. Instead of saying it, he just pushed the feelings back and carried on dealing with the mission at hand, and told Q to lay a trail of breadcrumbs for Silva.

The Second time he had attempted to tell Q was after he had returned from Skyfall. M might have been dead but he had never felt so alive and he thought that now would be the perfect time to tell him. James felt like he would just burst if he didn't do it today. Just as he was about to, there came a crippling worry that Q might laugh, or find it inappropriate to tell him something like that after M had died. Perhaps Q might think he was joking or it was too soon, Q might not even feel the same way as he. So instead, he just made a joke and walked away, mentally kicking himself for bottling it.

The Third time he had attempted to tell Q was just before he left for a mission. James had no idea how long he would be away, or even if he would return home in one piece. Q was explaining how to use some pieces of new equipment to James; he noticed how a lock of hair would sometimes fall out of place, and how he always smelled like Hugo Boss and that his glasses had his finger prints on the lenses. His breath smelled like Earl Grey, he must have had a cup about fifteen minutes ago. James loved the little details about Q that reminded him that he was more than just a letter, more than just a Quartermaster. He was a person, with thoughts, feelings and habits. The words could have easily slipped out of his mouth, but he couldn't say it. Instead, he bid farewell and left.

The Fourth time he had attempted to tell Q was a few months later. They had gone out to dinner to celebrate a job well done. Both of them wore their best suits and nicest smiles. Both of which Bond loved on Q. James took the liberty of ordering them both a beer with their meal. Q was so nervous that he knocked over his beer and managed to spill it all in his food. James couldn't help but laugh, and then the words came out without having to even think about it.
'I love you.'
There were a few moments of silence. Q looked over at him across the table then leaned over to kiss him.
'I love you too, 007.' Q sat back in his chair and started to mop up the spilled alcohol. 'Oh the amount of times I've tried to say it and failed.' He laughed and James laughed too, knowing exactly how he felt.