Won't Happen Again

6

Prompt from anon: Will and Erin talk about Jay's past (and yes Erin gets her payback... sort of)

/

It had started out as dinner and somehow ballooned from there. Now he was apparently taking her to the theatre as well. When he asked why she'd want to do all this with him instead of her boyfriend she'd laughed. "Jay can't eat Indian and he'd rather write parking tickets for a week straight then go to a musical." 

What he couldn't understand was how his slightly possessive little brother was so cool with all this. It hadn't been all that long ago that Will could wink at Lindsay and get a rise out of Jay, something Will lived to do as often as he could being one of the few joys of having a little brother. But when Erin emerged from the room all dolled up Jay had hummed appreciatively and complimented her sincerely.

"You're really okay with this? Me taking your girl out on a date?" Will asked Jay disbelievingly when Erin went back to the bedroom for something she'd forgotten.

"Better you than me," Jay laughed, remembering how his stomach felt the last time he'd eaten Indian food. "Besides it's not a date, it's payback. And you deserve it," Jay reminded him.

"I don't know, doesn't seem all that bad," Will shrugged.

"That's because you haven't paid for it yet," Jay chuckled knowing Erin had picked the most expensive Indian restaurant in the city and front row seats to the show.

"Come on Dr. Halstead, we have reservations to keep!" Erin called, coming out of the bedroom. She stopped in front of Jay. "You still working that concert tonight?"

"Yup, I'll text you later but I'll probably get home around the same time as you," he said leaning in to give her a lingering kiss, making Will roll his eyes and look away.  "You look beautiful. Have fun," Jay added then pinned his brother with a look. "No funny stuff, be a gentleman or you'll be in that cardboard box," Jay threatened.

Will smiled. There was the possessive little brother he knew and loved. But truth be told he had no plans on crossing any lines tonight. It was pretty obvious to anyone how solid Jay and Erin's relationship was. He was happy for his brother, if not a little envious at the moment. Besides as beautiful as she was, Will couldn't see himself with a girl that could kick his ass.

/

"So?" Will asked as the waiter took their menus away and went to fill their order.

"So?" Erin asked smiling back at him.

"What's new," Will chuckled at the awkward start they were having. It occurred to him if it weren't for Jay they'd probably never have cause to have a conversation, let alone a friendship or dinner date.

Erin laughed, "This shouldn't be this awkward."

"No, you're right it shouldn't. I'm just surprised this is what you chose as payback."

"Like I said, I love Indian and Jay can't stomach it and he hates musicals and I've been dying to see this one. I could have gone with a girlfriend I guess but I was kinda banking on you hating it as much as Jay and having to suck it up," Erin admitted. "Besides a free night out is always a plus for me."

Will nodded, "Well it definitely wouldn't be my choice of theatre show but I am looking forward to dinner," Will confessed. "Things seem really good with you and my brother," he observed, continuing the conversation.

Erin smiled, the dreamy heart eyes Will noticed she always got when someone spoke about Jay around her were on full display. He wondered if she realize she did that.

"They are, really good actually." She beamed.

"He seems really happy, actually to be honest, I've never seen him like this. I was worried about him for a bit there but he seems like he's in a really good place now. I'm sure you have no small part in that." Will complimented her.