Jack's been in love with his best friend for thirty years but he gave up hope a long time ago that Will would ever love him back. It hurt sometimes (when he allowed himself to really wallow about it, that is) but Jack mostly ignored his feelings because his friendship with Will was the most important thing and he didn't want to lose him (which he was absolutely convinced would happen if the truth ever came out). The incident with Michael sent Jack into a panic - thus why he went on the defensive just a bit - but he hated that Will got hurt in the end. That was one of the few times he hated being right. And of course, Michael hit the nail on the head with the accusation, making Jack wonder if he was really that obvious. He'd ask Karen and Grace if he wasn't terrified it'd get back to Will (which it no doubt would). And while he did have genuine feelings for Ben, it was intrusive thoughts about his best friend that led him to accepting a proposal from a guy he barely knew (which ended just as quickly as it began, thank God).
Karen's voice interrupted his musings, catching Jack so off guard he flinched. "What's going on in that mind of yours?" she asked him.
"You zoned out a while ago and it was scaring us," Grace informed him.
"Nothing. Just about the latest sales," Jack lied.
Karen and Grace exchanged glances, which aroused suspicions. "Yeah, we're not buying that." Grace, surprisingly, didn't want to push Jack because she too also worried about the outcome of any possible revelations.
Karen had overruled her, however. "When are you finally going to tell that man you're in head over heels in love with him?"
Jack's eyes widened and he wished he had a drink in his mouth so he could spit it out (sue him for having a flair for the dramatics). He laughed. "What the hell are you two ladies talking about? Are you drunk?"
"Always, but we're not talking about me, honey." Karen smiled triumphantly at him.
"You've been a little off lately and it took me a while to figure out why. Did Michael bring all that shit back up?" Grace correctly guessed.
Figuring there was no use in denying it, Jack finally nodded. "I'm not saying anything about it and neither are you. It's been thirty years. Something would have happened by now if it was going anywhere. And Will doesn't feel the same way about me - we've established that multiple times."
"It can't be worse than crying in the frozen foods aisle, right?" At least Grace hoped so.
He rolled his eyes. "No - this time we just have thirty years of friendship behind us! God, Grace! And you too, Karen? Really? How dare you betray me like this!" Maybe they were buying this?
No such luck, courtesy of Grace. "Cut the theatrics. It's not working at all, but I think you already know that. Sweetie, this is clearly killing you and you need to be honest with Will."
Karen took over from there. "She's right. Jackie, you're only hurting yourself now. I hate seeing you like this." She only wanted what was best for him; to see Jack happy. And that involved finally telling Will the truth.
"Why are you two meddling, and can you please get your own lives?" He really wanted to punch something now because they wouldn't leave him alone about this.
"Because we care about you, Jack," Grace told him.
That's when Jack finally realized this wasn't his apartment and he could leave so he stood up and walked out the door without saying a word to either of them, heading back to his apartment. Once he got bored because there was nothing to do, he wandered back over to Will and Grace's about three hours later. He stopped dead in his tracks the instant he stepped inside because everything got quiet. "What's going on?" he asked nervously.
"Nothing. Nothing is going on," Will answered, clearly lying.
Jack's heart started thumping in his chest as he started suspecting Karen and Grace had ratted him out. His palms sweating, he made his way to the couch and sat down, blood rushing in his ears. "Good to hear."
But the girls clearly weren't about to let this go. "Will," hissed Grace.
"Talk to him," Karen stage-whispered.
Jack wanted to flee but he couldn't move. "I don't know what you three have been discussing while I was gone but I hope it was about our dinner plans!" Even he cringed at how desperate and panicked he sounded. Acting on instinct, he stood up and tried to bolt but Will stopped him.
"We need to talk."
Jack tried to joke it away in hopes of defusing the situation. "Are you breaking up with me, Will? I didn't even know we were dating!"
"Don't do that. Be serious, Jack," urged Will.
The look on his face meant business, scaring the shit out of Jack even more. "I am, Will! What are we eating tonight?"
"Should we go?" Grace whispered to Karen, loud enough for Will and Jack to hear.
"No," Karen answered her, hoping they wouldn't have to deal with a fallout of epic proportions. She was rooting for a happy ending for them because they deserved it.
"You're in love with me, aren't you?" Will folded his arms and waited expectantly for an answer.
"Of course not, Will! Honestly, I can't believe you're even asking me that question. The answer is no. It will always be no. And that's the last time we've ever talk about this. If I didn't know any better, I'd say you were in love with me." Jack scoffed, hoping none of them could see through his obvious misdirection.
Will shook his head. "No, I'm not letting you get away with it this time."
"Why are we even talking about this in front of Grace and Karen? This is a private conversation, ladies! We don't need you here," Jack deflected.
They refused to budge and Will continued to stand his ground, ignoring both women. "I have a question for you, Jack."
Jack eyed him warily. "What is it?"
"Are you tired yet?"
Jack couldn't help it - he laughed just a bit. "Low blow, Will Truman."
"Answer the question - aren't you tired, Jack?" Will pressed yet again, already knowing the answer.
Jack steeled himself for the rejection and looked Will directly in the eye. "Yes," he admitted, the world dropping out from underneath him.
Will's mouth dropped open at his confession, and Jack didn't even wait for a response - he turned around, fumbled with the doorknob for about fifteen seconds longer than anticipated, and proceeded to bolt the whole way out of the apartment building. This story wasn't going to have a happy ending, which he had known from the beginning. Will and Jack's relationship had just been irrevocably changed no matter what.