Prompt: You've got a date tonight and you asked for advice on what to wear but I'm so in love with you and damn you look good in the outfit I picked out for you.

Nothing felt right.

She'd never been the kind of girl who had to buy a new outfit for very occasion, and yet, after throwing yet another dress down on her bed, April was seriously considering it.

This felt like the worst part of trying to put herself out there again - the trying to make sure she looked perfect and confident and the right level of sexy, without trying too hard. It was kind of exhausting, and she hated it. She'd never had to try so hard with Jackson, because their relationship had kind of come out of nowhere in a way. There had been no putting on her nicest dress and a full face of make up in the beginning - just that night at the boards and an eventual fast-forward to a wedding.

She let out an exasperated sigh, looking down at the discarded dresses on her bed and trying to reconsider one of them, as she was slowly but surely running out of options.

Jackson makes his presence known at her open bedroom door, raising an eyebrow at her. Presumably he'd heard her numerous sighs and sheer frustration over the past half an hour, and wondered what the hell was going on. "You okay?"

"Yeah...yes...I'm fine. I just...I have a date tonight and I don't know what to wear, and Arizona isn't responding to my texts!"

He blinked a few times, gulping and wondering what the right thing to do here is. He'd always been good at calming her down, but they'd agreed to have boundaries (even if they were living together and that made things complicated at times), and discussing her dating life recently had made him feel...weird. (but definitely not jealous.) "She's probably in surgery?" He tried to assure her, noticing the pile of dresses on her bed - a few of which looked familiar to him.

"I know but...I could really use her help right now. I don't know what I'm doing here, ugh, maybe I should just cancel!-"

She was spinning out, Jackson couldn't help but notice, so instead of wandering off down the hall, he decided to swallow his pride and enter the room, examining the array of dresses on the bed. There was maroon one he hadn't seen before, the green strapless number that she'd worn to Bailey's wedding (that had driven him crazy), and a navy blue one with pink flowers on it that was very her. He picked it up and handed it to her, "Wear this one."

April looked at him with a somewhat confused expression, wondering why he was helping her given how awkward their dating conversations had been, but grateful for the help nonetheless. "Uhm...thanks. I'm gonna...get ready then."

Jackson nodded in response, awkwardly leaving the room and shutting the bedroom door behind him so that she could have some privacy, before making his way to the lounge to put on a game. That usually helped to distract him.

An hour went by before April re-emerged from the room wearing the dress he'd picked out and with her hair perfectly curled, and he couldn't help but feel sick when he realised why the dress had looked so familiar to him. It was the same one she'd worn when they'd gone out for dinner before getting divorced, and he'd remembered how he couldn't avoid checking her out when she'd left early to answer a page. It looked just as amazing on her now as it had then, and there was a part of him that couldn't help but wish it was him having dinner with her again. (but again, he definitely was not jealous. Just...confused.)

"Okay, I'm heading out. Thanks...again, erm, for your help," April commented awkwardly, "Call me if you need me? You know, if anything happens with Hattie."

"Right, yeah, of course, no problem," He replied just as awkwardly, feeling himself stumbling over his words, "Have...fun?"

April just nodded, grabbing a jacket before leaving, and Jackson finds that the game on TV is no longer an adequate distraction for whatever it is he's feeling.