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"How do you feel about drowning out sorrows?" He looked at James in quiet shock. For one thing, his crush was wanting to have a drink with him. For another, since when did James Olsen have sorrows?
"I know what my sorrows are. What, uh... what sorrows exactly do you have, sir?"
James just laughed and replied "Bottoms up."
"What are you doing, man?" He had to ask. He knew it would hurt giving his crush girl advice but he couldn't just stand by and watch him fall. James didn't deserve that. James deserved to rise above not fall below.
"Having a drink with a friend."
"No. With Kara." This was the last things Winn wanted to talk about but it was clear James was hurting. James just looked at him with a confused expression and he realized James would just keep denying unless he outright said it. "Why did tell her you were happy about her and Adam?"
"Because she likes him." James said it like it was the most simple and obvious thing in the world and in the end he supposed it was. After all he was doing the same thing with James right now. But apparently James wasn't done because he added, "and that's what she wants me to say, man. Come on."
"No!" Even if he couldn't be with James himself he would make damn sure that James was happy. Even if it meant he had to give James the push he needed to be with someone else.
"Look, look... Dude, I've been stuck in the friend zone so long that I'm just thinking about buying some investment property here." First it was with Kara. Now it was with James. Honestly he should listen to the advice Alex gave Kara. Stop listening to the girlfriend problems and be the girlfriend. Or in his case, boyfriend. But he couldn't help it. His self esteem was low enough to think that his feelings didn't matter as much as everyone else's and he just wanted the people closest to him to be happy.
"But you, you could be with her, and you know it. Literally, all you have to do is say the word. So why don't you?" Part of him, the selfish part, wanted it to be because James liked him. Not Kara. Not Lucy. Not Superman. Not anyone else. Him. But he knew that was false and would always be false no matter the circumstances.
"Winn, I'm in a relationship." All he could do was shake his head and get ready to give an epic monologue to try and convince James to let himself be happy for once instead of doing and being what he thought he had to.
"Look, dude, I know that you care about Lucy, you don't have to convince me, I get it. But nobody want's to be in a relationship with someone who wants to be with somebody else." God knows that was why all his attempted relationships failed.
James just nodded and contemplated his words. He clapped his hands together and said, "Good talk."
James agreed and started to leave, talking the drink with him. "Leave the bottle."
He really needed to drink and clear all the thoughts out of his head. He really didn't want to spend tonight pinning even more than he already had. He watched James go and felt his chances of ever being with James vanish completely. He sighed and took a big swig out of the bottle before returning to work once again.