Five would drunkenly propose to you all the time. He also pranked you on April 1st, but that was just a joke. You always thought it was just the alcohol talking, but alcohol always lets loose the thoughts that people think when sober. You always would find it funny when he would "propose". He would get down on one knee and grab the closest object to him, which was sometimes a book or a bottle of alcohol, and propose to you with it. He'd call you "his new Delores". You'd always laugh and shake it off, telling him to try again when he's sober. You never thought he'd actually do it.
From the first time Five had made eye contact with you, he knew you were the one. The one he wanted to spend the rest of his life with. He wanted you to be his wife, but didn't know how. He heard about all of his drunken tries. He wished he was that confident sober. Five kept thinking of ways to do it. He couldn't really think of anything. Until one day...
The two of you were in the kitchen and you had said that one of your friend's boyfriend had proposed to her and he did it where they first met. A light bulb went off in Five's head. He was going to propose in the Academy. But first he needed a ring. He had asked Klaus and Ben to come with him. He figured Klaus and Ben would know what you wanted because the three of you were best friends. The minuet Five walked in, he lost Klaus, shocker. He found him by some rings. He was furiously pointing to one with a small diamond and a simple band.
"THIS ONE! She mentioned she liked simple and this is as simple as it gets!" Five looked down at it. He knew that it was THE ring. With the approval of Ben and Klaus, he bought it. He know just had to plan how he was going to do it.
He sat in the big living room and thought about how he wanted to do it. He thought that maybe he should just bring her in here and drop down on his knee and propose. He thought that was stupid and scrapped that idea. He kept trying to think when Klaus ran in. He was out of breath and was bouncing from foot to foot.
"Flash mob proposal." Five furrowed his eyebrows.
"What?"
"She said that she wants a flash mob proposal." Five looked at his brother in confusion. "Oh my god! Flash mob proposal! You do this crazy song and dance number in public and by the end you propose." Five, he doesn't know why, but he agreed to do it. He started to plan it and then realized something.
You get really anxious when all the attention is on you.
He knew that plan was a lost cause then. He then decided to do it at a fancy restaurant. Simple and boring, but it would do. He took you out on a Saturday to a really nice and fancy restaurant that Allison recommended. When he walked in, he got so nervous. His hands fidgeted and he couldn't calm down. Halfway through dinner, you got up to use the bathroom. He took that time to try and calm down. By the time you got back, he backed out of his idea.
It was a week after, Five was sitting in his room when the alarm sounded. It was time for another mission. Every academy member was ready and waiting for Five. He didn't know why, but he grabbed the ring. He sat next to you on the way to the mission, which was a robbery. When all of you arrived, you snuck in and started fighting the robbers. As you were fighting a robber, one of his buddies pulled out a gun and pointed it at you. Five saw this and right as the shot rang out, Five teleported over to you and then teleported the both of you away from the fighting.
He hugged you close and made sure that there were no bumps or bruises on you. He then grabbed on to your hand. You looked at him confused until he pulled out a ring. Your eyes widened as he put it on your finger. He looked up at you with hope in his eyes.
"Marry me?"
"Bout time, old timer." You smiled and walked away to kick the ass of those robbers, especially the one who tried to shoot you. As you guys got back, the mission being complete and you kicking the ass of the shooter, all of you separated to their respected rooms. Klaus said he'd see ya later, that he had to yell at Ben for punching him in the fight instead of the robber he was fighting.
You walked into your room and smiled down at the ring at your finger. Five appeared behind you and pulled you by your waist, close to him as possible.
"You never really gave me a definite answer." You looked up at him and smiled.
"What?"
"Yes or no, honey."
"Rings on, ain't it?" With that, Five pulled you closer and kissed you. You, of course, kissed back and couldn't wait for the day you two say 'i do'.