The thing is, once Michael puts the idea in his head that Jack is in love with him, Will can't stop thinking about it, even after their conversation. He can't figure out why either - why can't he stop going over the last thirty years of their friendship in his head? And of course, his mind goes to that night at D'Agostino's all those years ago, when Jack confessed his love and tried to play it off as a test. But was it a test? And why is Will questioning everything now? Jack isn't in love with him, and he's not in love with Jack. Besides, things have settled down since their talk. It's best to leave things as they are and ignore whatever the fuck is going on in his mind right now. Their conversation the other day after his break-up with Michael should be the end of it - it's always best to leave the past in the past, something he should have learned before getting back together with his ex-boyfriend. "Will!" shouts Grace, interrupting his train of thought.
He flinches and looks up at his best friend. "What?" he asks her, slightly irritated.
"Why have you been staring into space for the past ten minutes? I paused the movie and you didn't even say anything," she points out, worried about her best friend.
"Nothing. And why'd you pause the movie in the first place? We should get some popcorn." He's aware that he's changed the subject rather abruptly and hopes she hasn't noticed.
No such luck - Grace only glares at him. "Will, something's wrong, isn't it? Please tell me what is it - maybe we can talk it out." She just needs him to open up to her.
The sheer thought of telling Grace what's been repeating on a loop in his head for the past few days makes him panic. "Grace, nothing is wrong. If there was, I'd tell you, okay? Now let's get popcorn," Will tries, hoping to dissuade her from bothering him about this again.
A skeptical Grace sighs and stands up, heading towards the kitchen. "I'll get it out of you soon, William Truman," she vows. Grabbing the popcorn out of the cupboard, she unwraps the packaging and sets it down on the microwave, pressing the timer. Something's been off with him since the break-up with Michael (she doubts that's what's bothering him) and she can't figure out why - she'll get to the bottom of this and doesn't care how long it'll take to pry the truth out of him. But letting it go for now, she dumps the popcorn into a bowl and returns to the living room to continue watching the movie.
Will zones out several more times but Grace doesn't dare say another word to him about it.
Two weeks later, Will is falling apart at the seams. The others have noticed something's off but he can't bring himself to talk to any of them. Why can't he stop thinking about Jack's possible feelings for him? He's one of his best friends - that's all they are and ever will be. What's the sense of wondering about what ifs? If they had ever tried to date in the past, it likely would have ended badly and ruined their friendship. The same is still true now. He doesn't even want to be with Jack so there's no use continuing down this path.
Jack sips his drink, continuing to wonder why Will's been acting so weird lately. "You need to relax," he tells Will, patting the couch.
The last thing Will wants to do is get drunk and spill everything to Jack but he also needs to let loose and finally relax. So he sits down on the couch next to Jack and grabs his drink. "Thanks," he tells him.
"Hey!" an outraged Jack shouts, glaring at him before standing up and walking to the kitchen to make another drink.
"Sorry! I'll let you have my next one," Will promises.
"You better," Jack shoots back.
The two of them get drunk off their asses and watch TV all night, and it's the most fun Will's had in a long time (he doesn't want to think about why and ignores it in the days following).
Grace finally snaps and decides to confront Will about whatever's bothering him just six days later. "What the hell's going on with you?" She's worried about him and is panicking that something's wrong. It's freaking her the fuck out, not knowing what's he's going through.
Will laughs and it rings false in his ears. "Nothing's the matter with me."
"Will, really? Have you listened to yourself the past few weeks? You're scaring me."
He sighs. "It's nothing, Gracie."
"Don't lie to me - you know better than that. Maybe you'll feel better if you just tell someone?"
He knows he has to bite the bullet on something and decides to tell her a half-truth. "I've just been thinking about my life - relationships, mostly - since Michael and I reconciled and broke up again. It brought back some shit. That's all." Will really hopes she buys it.
She does but Grace can tell that's not all that's bothering him. "I'll be here when you're truly ready to talk," she tells him, pulling Will in for a hug.
He melts into it, so thankful she's in his life and won't push him for once. This is something he needs to work through on his own and once he does, everything will go back to normal. "Thanks," he murmurs.
"You're welcome." She pats his shoulder and then the two of them leave for work.
It isn't until three weeks after that, when Jack's telling an asinine story that makes Will laugh so hard he can barely stand it that he finally figures out why he's been freaking out for over a month. He instantly stops laughing and freezes. Jack, who had been enjoying telling his story, eyes his best friend in concern. "Uh, Will? You okay?"
Will waves off his concerns. "Yeah, I'm fine. Just realized I forgot to turn off the fridge before we left the apartment?"
Jack cocks his head in confusion. "What?"
Panicking, Will can't even think straight. "Did I say fridge? I meant stove?" He tells Jack goodbye then flees back home, only to find Grace sitting in the living room, feet kicked up on the table and eating cake.
"Did something happen? You're pure white," she observed.
"Fuck," Will mutters repeatedly for about five minutes before Grace gets fed up and shakes him to get his attention.
"What happened?" she presses, hoping no one's hurt or dead. Her mind's whirring about worst case scenarios.
Will bites his lip and afraid to say it out loud, plunges ahead anyway. "I'm in love with Jack."
Grace's mouth drops open and she gapes at her friend. "What? How? When?"
"That's exactly what I'd like to know!" He waves his arms around and collapses in a chair. "Michael thought Jack's been in love with me all this time, and I couldn't stop thinking about it. He did confess his love for me thirty years ago and then tried to play it off as a test but come on. And Jack denied it, of course, when I confronted him, but what if he was lying? And I was laughing at one of his stories, and it hit me like a sucker punch. I'm in love with Jack," he confesses in a rush.
Still reeling from his confession, Grace peppers Will with questions. "Are you sure? Are you going to tell him? This is so exciting!" she squeals, surprising even herself. Why is she so happy about this? She can't figure out why but Will's her main concern right now so she brushes aside her own feelings for now.
"Yes, I'm sure. I just said it twice!" he shouts.
Grace rubs her ear, glaring at him. "Okay, Will, calm down a bit, okay? You don't need to freak out about this. Just tell him the truth," she encourages.
"He doesn't feel the same way about me. And how am I supposed to bring this up after our conversation? We agreed that we'd stay friends and wouldn't ruin our relationship."
"But that was before you figured out your feelings for him, Will. That changes everything. Take the initiative for once in your life and confess your feelings. It'll work out," she tells him, pulling him in for a hug.
Will calms down just a bit and can't focus on anything else for the rest of the night.
Disregarding Grace's advice (for now, at least), Will pushes his feelings for Jack aside and buries himself in work. Surprising her two friends, it's Karen who winds up confronting him. "Grace told me about your little problem," she says, sauntering up to his desk.
"Grace!" Will hisses. "I told you that in confidence."
"Oh, please, Will. I was about to burst, especially since you're still in a little bit of denial."
"I am not in denial!" He's just ignoring his feelings in a multitude of unhealthy ways (like eating a shitload of junk food).
Karen lifts his chin up so she can look directly in his eyes. "Honey, Jack's never said a word to me about this but that boy is head over heels in love with you. Don't you dare hurt him," she warns, deadly serious.
"He's head over heels in love with me?" Will repeats, slightly dazed.
She rolls her eyes. "Do you ever listen to a word I say?"
"Sorry. But you want both want me to tell him."
"Will, this is killing you keeping your feelings locked up inside. Get the fuck out of here now and tell him," Grace responds.
Will's hands are starting to shake and he sits on them for a few seconds to still them. "Are you sure?" he presses Karen.
"William! Go tell him now," she orders, frustrated with his behavior. She - well Grace, that is - hasn't gotten any work done the past few days because they've been so worried about Will.
"Fine!" He puts his hands up in the air and then leaves in a hurry. Fortunately, he hails a cab right away and then rushes up the stairs once he gets back home. He repeatedly knocks on Jack's door, trying to keep himself calm.
Opening his door, Jack only stares at him in confusion. "What's going on? Shouldn't you be at work?" he asks as he lets Will in.
"Yes, but Grace and Karen sent me over here to talk to you about something important."
The two of them sit down on the couch and Will grabs Jack's hands. "I need to know - are you in love with me?"
Fear flashes across Jack's face so briefly that Will wouldn't have been able to recognize it if he hadn't been looking for it. Jack rolls his eyes and laughs scornfully. "Haven't we already been over this? Are you feeling okay, old man? Do I need to take you to the doctor to have you checked out?"
Will snorts. "Jack, I want you to listen to me very carefully. I'm not asking this to hurt you or for you to lie."
"Okay? Why are you asking me again?" Jack asks, confused and trying not to get his hopes up. He can't go through this again - one more rejection might actually kill him.
Will bites his lip and decides to finally say it. "I haven't been able to stop thinking about our relationship since Michael brought it up." He grabs Jack's hand and squeezes it, the action comforting him just a bit.
"Why? We're better off as friends," Jack lies, his hopes finally starting to rise.
He sees right through him and grins. "It's taken me such a long time to realize this but I'm in love with you, Jack. That's why I've been so on edge and weird lately."
In a little bit of shock, Jack's voice cracks and he has to clear his throat before he speaks. "Say that for me again."
"I'm in love with you," Will repeats.
Jack can't help but tear up. "Wow. I hoped over the years but I'd never thought I'd hear you say that to me. Am I dreaming?" he asks in awe.
He shakes his head. "Nope."
Jack surges forward and kisses him. "Hi," he says excitedly.
"We definitely need to kiss again," Will tells him. "Just to see if we're a good match."
He laughs. "I'm in. Who knew we'd end up here after I ended up crying in the frozen foods section at D'Agostino's? I had hope at first but it gradually faded away. I wanted you in my life any way I could get you because I didn't want to lose you." A tear slides down Jack's cheek and Will wipes it away before he kisses Jack once more.
"Can we come in now?" Grace yells through the door.
"We're dying out here!" Karen cries, buzzing with excitement.
The two of them laugh. "Come in," Will says and isn't surprised when they burst through the door.
"Were you eavesdropping the whole time?" Jack asks, already knowing the answer. When they both nod, he only laughs. "How could I be mad at you for that when I'd do the same in your position?"
"I'm going to get ordained and marry you someday soon," Karen promises, swooping in for a hug after Jack stands up, still holding Will's hand.
"Don't get too far ahead of yourself. We only just admitted our feelings for each other," Will tells her, even though he has a good feeling about where this relationship is heading.
"You two have known each other for thirty years. I don't think anybody's rushing into anything." Grace is so happy for them she wants to cry (but she holds back because this isn't about her).
Will and Jack have to catch up on thirty years of missed moments and they're not about to waste a second. So they kick Grace and Karen out, and make out against the door for a little while.
It's taken them a long time to get here but Will and Jack have no regrets about the speed of their relationship. They needed to grow up and have a lot of experiences in life before they could come together to make this work. They're definitely enjoying this new turn and can't wait to see what the future holds for them. And of course, Grace and Karen are their cheerleaders, supporting them every step of the way. Their lives are pretty fucking amazing.