Jay is sitting in his apartment having a beer with Will. Normally he'd like to say he's enjoying this brotherly bonding time, but not tonight. No, tonight, Will is trying to convince him to go on a double-date with him. Actually, 'begging' would be the appropriate term. Some girl Will met at the hospital agreed to go out with him if she could also bring her single friend along. Naturally, Will figures he can rope him in. Jay wants to believe he's hesitant because he hates blind dates, especially doubles, but deep down he knows more of it has to do with Hailey. Which is stupid when you think of it because him and Hailey aren't together, have never been. Why should he let his feelings for his partner interfere with meeting other women!? He takes a big gulp then, knowing he doesn't want to contemplate that thought for much longer.
"Oh c'mon, it will be good for the both of us! Stop being such a stiff!" Will pleads.
"It's just not my thing man. I don't even know this girl, why would I want to go out with her? And with YOU there, seriously?"
"Because she's attractive… and at this point you haven't gotten laid since the first 'Avengers' movie came out!" Will jokes.
"Very funny… I am perfectly fine with being single right now."
"Yea right, if Hailey came waltzing in that door now and confessed her love for you, you'd practically put a ring on it before you could get the words out."
Jay gives him a death stare. He still does not want to discuss his relationship with Hailey with him. His feelings are complicated enough as is. He's certainly not going to confirm, or voice them to his brother.
"Not this again, Will. I told you, Hailey and I are friends, can we please leave it at that!?"
"Alright, whatever. But y'know, maybe seeing you with another girl will make her realize you are in fact, still interested in women. Jealousy is a powerful drug."
Jay rolls his eyes at that, but he must admit he is a bit intrigued. He can't help but wonder how Hailey would react if he was dating someone. He's well aware of how he reacted to her being with Adam. Still, it's not his style.
"Will, you're like a 17-year old sometimes, y'know that?"
"I'm just saying… anyway, c'mon Jay, I need this, do it for me!"
"Just tell this girl you're not into double-dating, especially on a first date. I'm sure she'll understand… who brings a friend along anyway?"
"She said her friend was going through a tough time and that she'd feel guilty going out and having fun without her."
"Oh great, you're really selling it now Will!" Jay jokes.
"Look, you do this for me and I swear to never bring up the Hailey thing again. You go on living in your denial world without my prying!"
Jay seriously ponders Will's request this time. It's frustrating enough sorting his feelings for Hailey on his own, let alone when Will tries to question him five times a week about it. What's the worst that can happen, it's just one date? Hell, maybe he'll actually like the girl and can move on from constantly wanting to be with his partner. He knows in his heart that's not going to happen, but a guy can hope, right? It's not like Hailey is going to be making a move on him anytime soon, or ever! He can enjoy himself in the meantime and get Will off his back.
"Okay, deal!" Jay extends his hand to shake Will's.
"Pleasure doing business with you!" Will smiles, clearly pleased. Jay sincerely hopes this won't be a mistake. He takes another long sip of beer as Hailey crosses his mind again.
Hailey studies Jay as they sit in the squad car for an extra overtime shift. It's been weeks now since her and Adam broke things off, and if anything, her feelings for Jay have gotten even more confusing. The two of them are still spending a good amount of time together, and she just can't seem to shake the feelings off. It was one thing when she was still with Adam, at least she could pretend that he was the guy she was truly interested in… but now, she practically has no distraction from it. And it's certainly not like her and Jay has dared to address the elephant in the room aloud. She's actually starting to question if she should broach the subject one day, just to get it off her chest finally. But for the life of her she just can't seem to get ready to.
"So I had another interesting conversation with Will last night." She hears Jay say to her.
"Oh yea? What now?"
"He wants me to go on a double-date with him and some girl he met at Med." He says, and for a moment Hailey swears it looks like he's gauging her reaction to that.
Seconds go by and she still doesn't know how to respond, feeling a massive wave of jealousy spread through her. Why should she be jealous? It's not like her and Jay are together, and it's just a date. He had to see her with Adam all those months. Besides, it's like she's been trying to convince herself these past couple years, they're partners… and they shouldn't cross that line, especially with romantic entanglements. So why is she so disappointed? This could finally help settle whatever feelings they're burying deep down and clearly avoiding.
"Oh? Well, that's certainly interesting… did you tell him you would?" she finally responds.
"I did, yea. After much debating, I finally agreed, but I'm still not sure I want to. What do you think I should do?"
"Jay, I don't think it's my place… it was one thing with Camilla telling you what to do since it involved the job… but I probably shouldn't get involved with your average dating life." She says, really hoping to avoid the subject altogether.
"Your opinion means a lot to me, Hailey… and I just thought you might have some other input I'm not seeing…" he says to her hesitantly.
She wonders if he's trying to make her catch that double-meaning, but for her sanity at the moment she does her best to not over-analyze it. While they very well may need to talk about them one day, on the job and stuck in a car is certainly not the time or place.
"I mean, it's just a date Jay, right? What's the big deal?" she says while looking down, picking at her finger and avoiding his eyes.
"So you think I should go then?"
"Maybe, if you want to. At the very least, it'll get you out of depressingly drinking shitty beer with me for a night." She tries to make a joke, and they stare at each other smirking. Their gaze lasts for a while, and Hailey contemplates saying something else, but hesitates. Jay waits, expecting more, but when he doesn't get it he finally just nods back at her.
"Guess you're right. I'm making a bigger deal of it than I should…" he finally responds, slightly melancholy.
Hailey doesn't know what to say anymore. It's all just too complicated. Her heart wants to scream at him and tell him to go out with her instead, but her stubborn head knows she can't. She thinks that Adam would kill her right now for missing this opportunity to have that talk with Jay… but that's how they always differed. Adam loves wearing his heart on his sleeve, and as for her, she'll do anything to keep hers trapped in a hoodie. Luckily Jay takes pity on them both at the moment and changes the subject completely.
"So you still down to meet everyone at Molly's tonight once we get off?"
"Yea, we probably should. It's been too long…" she says, this time her voice laced with a double-entendre. They sit there quietly for the next hour, neither wanting to reveal any more than they already have. The tension between them obviously getting more palpable by the day. They're nothing but consistent at least, Hailey ponders sadly as she stares out the window.
[A/N: Apologies for an angsty one, but I need this to help set up something in a future chapter. Hoping the show gives us some good Upstead moments when it returns to loosely base things on before I epilogue this particular story. Well, if I'm being honest, I'm just hoping for more Upstead moments in general leading to them getting together by season 7, haha! Thank you again for all the incredibly kind reviews & continuing to read, it means a lot!]