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So he started planning out the best date and time to propose to you. He probably looked a little crazy to his siblings as he set up a cork board in one of his many safe houses with ideas and dates.

Dick was the only one that thought his planning was sweet, everyone else thought he was stressing out about your answer. And maybe in a different time he would be but after three years of you staying and reassuring him that you wanted him he was sure that you would say yes.

He had the ring custom made with your anniversary etched on the inside of the band and a garnet in the center alongside two small diamonds. Dick and Roy had helped him pick it out, they argued most of the time but in they end helped, three months before he planned to propose.

There were multiple phone calls from his brother and best friend to hype him up in the two days before he planned to propose. He had outwardly scoffed at them calling him to tell him that you would obviously say yes but inwardly he appreciated the support.

When you walk out of your shared bedroom he almost gets on one knee there. You look radiant and Jason almost forgets his whole plan. He restrains himself because him proposing before dinner wasn’t planned.

First, Jason takes you to the bookshop where you met and has become a semi-frequent date spot.

It’s a small hole in the wall shop that really only people know in the upper east side know about. He knows the owner, an older woman named Meredith whose family had this shop for generations, and she was extremely excited to know that you two were getting engaged. She keeps it a secret for him but does give him a discount on the books you end up buying.

He really enjoys watching you read through the backs of books with a slight pinch between your brows. You eventually end up getting two since you couldn’t decide between them.

After you finish up at the book store he takes you a couple blocks down to an Italian restaurant that he knows is a front for the mafia but makes the best cannolis he has ever had so he lets it slide. You talk about your work, friends and anything else that comes to mind and Jason is happy to watch you talk.

When the check is dropped off by a gruff looking guy who gives Jason a knowing smile you reach for it and Jason lightly smacks your hand away from it.

“Nope.” He states simply.

“Jay-” You go to protest with a frown on your face.

“Nope!” His voice increases in volume as he takes the bill away from your hands.

You give him a huff and an eye roll before giving in. Jason feels particularly accomplished as he walks up to pay the bill.

Once the bill is settled Jason leads you back to your building and up to the roof.

He had some help decorating the roof since he was with you for most of the day. Steph and Cass had taken point on that because Steph had told him that his taste was tragic, Cass had agreed before pulling out Bruce’s credit card that she swiped off of him somehow.

“Jason.” You gasp softly at the lit up rooftop decorated with pillows and blankets for stargazing. “This is beautiful.”

He runs his hand over the back of his neck in embarrassment, “I just came up with the idea, Steph and Cass set everything up.”

You squeeze his hand softly, “You still thought of it and that’s what matters.”

Jason takes a deep breath, reaching for the ring box in his pocket. “I also have something else.”

You get a confused pinch between your brows that evens out into shock as Jason gets down on one knee.

He goes to say the long speech he had planned, the one where he told you how much you mean to him, how you love him the way he is, how you make him want to live again rather then just survive. Jason had pondered what to say for months.

But now as he look up into your shocked face and teary eyes his brain stutters to a stop.

“Please?” Jason breathes out, no other words in his mind.

“Yes.” You sob and throw yourself into his arms. “Yes! Oh my god Jay. Yes.”

Jason holds you with a smile on his face that’s so wide it hurts because you love him when he has a plan and even when he doesn’t.

Mary when clark showed his map of the backrooms