Jack finished off his second whiskey and ordered another. It took him a while to build a buzz, and it never lasted long, but in this case that would likely work in his favor. The last thing Adam needed was a confidant as drunk as he was.
"But you care for her," he said, with a knowing nod. "Sounds rough. In that case, a riddle sounds as eloquent as a love letter. You should send it. Tomorrow, maybe." Tonight, he had a feeling any 'love letter riddle' would end up being a maze with a heart at the end.
The question gave him pause. He had to weigh how to answer it, and the hesitation was probably indication enough that the subject carried a great deal of weight. "I have," he said. "Once." He downed half the whiskey, nearly stopped, and then just drank the rest. He felt very aware of the pair of rings hanging against his skin under his shirt. It had been the first thing he'd checked for when he woke up from being dead in his belongings. The autopsy was the first time it had been removed since he put it on over a year before.
"You want my honest advice?" he said, looking over at him. "You can send her all the riddles you like, but don't wait too long. Don't be afraid to talk to her directly about what she means to you. People...we take them for granted. We think they'll be here forever, and then they can be gone in a moment." His eyes were intent on the empty glass of whiskey, narrowed slightly in thought. "You'll only end up alone, and measuring every grief you meet with probing eyes. The regret, it isn't worth holding back for. I understand - Daryl, she sounds like a complex woman, the sort that may take some time to bring around, but something happened last night, didn't it? I wouldn't waste that. You've been presented with an opportunity, so whatever you're going to say to her - make it count. If you care about her, whatever your other feelings for her, she should know it."