Prompt # 13: "It's Midnight, where the hell were you?"
Hailey and Jay were finally relaxing on her couch and watching TV after a long day of errands and Hailey packing for their trip in the morning. The two were finally going on a much-needed vacation, heading up to northern Michigan right on Lake Huron first thing in the morning. To say they were excited was an understatement. Jay however seemed a little bit off for the past few hours. At first Hailey was chalking it up to wound up eagerness to go, but now she was getting slightly suspicious. His leg was shaking, keying her in to all kinds of nervous energy.
"Hey, everything alright? You've been acting a little strange since dinner." She finally questions.
"Yeah, of course. I'm going on vacation with a beautiful woman tomorrow, for hopefully 7 days of nakedness, what could be wrong?" he boyishly smirked and did his best to deflect.
"Well, you're sure of yourself, aren't ya? Who says I'm spending all that time naked?" she raises her brow, but smiles.
He leans in to kiss her softly and she gladly obliges. Their heart rates are racing when they finally pull back. "I was just hoping to make some new memories for when we're old and grey together."
"Alright, I can promise you 5 days of naked time, 6 if you play your cards right. Speaking of, we should get to bed, we're waking entirely too early for me tomorrow." She gives him another quick kiss as she stands from the couch reaching out her hand for him to join her.
"I'll be in in a bit. Want to catch the end of this A's game."
She gives him an odd look but doesn't push too much. "Since when are you into West Coast baseball?"
He laughs it off, his leg twitching again. "I'm not, but Ruz got me to place a bet on this game with him so I just want to see how it shakes out."
"Alright. Well, don't be too long, you're cutting into naked time!" she teases with a wink and starts to head upstairs.
Once she's out of sight, Jay starts checking his phone again and pacing the room. He's ready to have a full-on freak out. All of his texts have still been unanswered.
"C'mon Vanessa, what the hell are you doing?" he mumbles to himself in frustration.
A few days ago Jay had entrusted Vanessa with a gift he had for Hailey that he planned to give her on their trip. Apparently Vanessa had "guys" too and she ensured him that her engraving one was the best around for the price. She had promised Jay that he could get it done well in time before him and Hailey left. But Jay was losing his patience as it was supposed to be ready yesterday, but Vanessa said he got backed up. She swore to him she'd have it after dinner tonight. Now it was almost midnight and he's ready to lose it. He wants everything to be perfect and this isn't a great start. Another few minutes go by when he decides to check in with Hailey, maybe she's heard from her roommate. He heads upstairs to her, well at this point it might as well be their room and finds her in bed, the small lamp light on as she scrolls through her phone.
"Hey, you heard from Vanessa recently? It's getting pretty late." He tries to ask casually while standing in the door way.
She gives him another odd look. "She's a big girl, I'm sure she'll be home before the night ends. You sure you're alright?"
"Yeah, sorry, just noticed the time and realized she never responded to the sports betting group text." He hopes explains his wondering question off.
"Oohkay. Well if I hear from her I'll be sure to tell her to reply. But hun, why don't you come to bed? You've got a long drive tomorrow."
"The game's almost over. I'll be up soon, I promise. I'll even buy coffee in the morning."
"Well I think I'm gonna turn in. Getting kind of tired. I hope they win."
"Thanks babe. Sweet dreams… of me!" he grins hoping to ease her worry and suspicion and earning himself an eyeroll.
Back downstairs again, he's ready to kill Vanessa. He's an excellent detective, they'd never find the body. The stupid baseball game is even almost over at this point. He swears this is the last time he's using one of her guys. FINALLY a few minutes later he hears the front door being unlocked. He's up from the couch at lightning speed and practically sprinting towards his coworker. Vanessa looks shocked as she almost plows right into him.
"Jesus Halstead, ever heard of personal space?"
"It's Midnight, where the hell were you?" he demands softly to not wake Hailey, but it may as well have been a yell with the tone of his voice.
"Chill Dad! I was waiting for Leo to finish up the final touches. He did a great job, she's gonna love it." Vanessa says as she hands him the prized jewelry.
Jay finally lets out a breath he didn't know he'd been holding and allows his nervousness to ease some. "Thanks! Sorry, I just want everything to be perfect and you were cutting it so close I was starting to fear I wouldn't have it for this trip."
"Nah, I'm sorry. I should have texted. He wanted to give this his full attention, so he had to finish up a few of his other jobs before getting to it. No way would I have let him keep it past tonight. I know how important this is to you."
"Yeah." He says simply, a small smile forming on his face.
"So you think she suspects? She hasn't mentioned anything to me, which is good."
"No. Although after tonight, I can only imagine what she thinks. She knew something was up with me bouncing off the walls waiting for you. I told her we bet on a baseball game."
"Yuck. I hate baseball. But she knows how much I love making an extra buck, so I'm sure you're fine. It is late though, you probably should go join her in bed. Big week ahead." Vanessa winks at him.
"Thanks, Mom!" he replies, teasing her back from before. "Also, I'll have you know I missed out on naked time with your roommate due to waiting for you."
Vanessa gives him a look of disgust, even though she's secretly thrilled for how far the couple has come. "TMI, Jay! Have a good vacation. I expect pics!"
They smile and nod at each other as Jay makes his way back upstairs again. Vanessa wasn't wrong, it will certainly be a big week ahead…
It's day three of their vacation and they've had an absolutely amazing time so far. The house they rented was right on the lake and the area was the perfect amount quiet and busy for their taste. It was the perfect relaxation away from bustling Chicago, but also had enough to do to keep them occupied and restaurants to go to appease the foodie's in them. They were thrilled they chose there instead of spending more money to fly somewhere. And Hailey had been making good on her word, there had been days of nakedness already. The trip was going so well that Jay didn't even have time to think of being nervous for what was to come later.
Jay insisted that they pack food and go on a sunset boat ride since they had rented it for the week. Him and Will had both got their licenses years before. He's glad it could come in handy now. The further he drives out though, the more nervous he starts to feel. The weight of the jewelry Vanessa had engraved feeling like it was burning a hole in his pocket. All of his worries started to ease though when Hailey started to smile widely, taking picture after picture of the scenery. She had never looked more stunning to him than in this moment.
"This is beautiful!" she exclaimed, turning to face Jay as he idled the boat.
"Yes it is!" he looked at her straight on with heat and overwhelming love in his eyes.
"Jay…" Hailey whispered, still blushing even after them being together for almost a year now.
"What? I can't tell my girlfriend she's beautiful?" he chaffed.
"Of course. And you're not so bad yourself. We're just not normally so mushy."
"Yeah, but tonight's a special occasion."
"Oh?" she eyed him curiously. "You're not going to suddenly tell me you never really learned to drive a boat are you?"
"Funny." Jay said while fiddling with his hands, getting a little nervous again as he got closer to her.
"You're acting weird again. Is there another sports bet I don't know about?"
"No." he exclaimed while laughing and wrapping her into his arms as they both looked off at the setting sun. She leaned her head back into his chest and they stood quietly for a couple minutes just enjoying this time together.
Finally Jay spoke again. "I want you to reach into my pocket."
"What? This isn't some awkward come-on is it?"
"Just do it!" his voice light from his smile as he speaks near her ear.
She obliges and reaches her right hand into his front pocket, feeling a small box. She gasps once she pulls it out and nearly drops it in the water.
"Jay!?.." she exclaims questioningly.
"Open it." He says calmly and watches her eyes well up with tears when she does. He finally turns her to face him fully and grabs the box from her hand. "Hailey, these past years being your partner at work have been the best of my life. And this past year of being with you whole-heartedly has been better than anything I could have ever imagined. You've made me a better man. You've finally made me whole. And I want you to be my partner in life for the rest of our years. Marry me, please?" he finishes the final part while getting down on his knee and extending the ring just as the sun has almost fully set.
Hailey's eyes well up even more and she's not sure how she's managing to still stand right now. She never would have guessed she'd have this in her cards one day, but Jay's proven to her that even someone with as damaged of a past as her is worthy of love. As their team always claimed, they fixed each other. So she managed the only response she could and finally got the word out… "Yes!"
Jay stood up beaming as he placed the ring on her finger and she pulled him in for a passionate kiss. He was definitely getting all 7 days of "naked time" for this. After a few breathless minutes, they finally pulled apart slightly; both admiring their hands as he held hers up with the ring shining.
"Oh, wait, I almost forgot. You have to look at the inside of the band." Jay murmured against her lips as she slipped off the ring again to peer at it.
Inside there was an engraving that made her tears fall even more.
I'd Follow You…
[A/N: Welcome to the 5th edition of the prompts list. This one comes thanks to requests by: "Rvb92," "JediA," and "guest." While I had thought this prompt would be great for 'Angsty Upstead' or 'Sexual Upstead' I figured there's others for that, plus this idea with Vanessa popped into my head & it's different. Hope it didn't disappoint. Thank you for reading and always being such a fantastic audience. Stay safe!
*The list of prompts are at the bottom of the first chapter if anyone wants to request one]