(New order! Oldest to youngest.)

Darry:
You guys live together already. He always makes coffee and then wakes you up. He told you he had gotten you a mug. When you saw the bottom of your drink you grinned and then looked at Darry, who was kneeling in front of you with a ring.

Tim:
It was your anniversary, and he decided to take you on a walk. He led you to this cleared out area, full of fairy lights and such. He got down on one knee and proposed to you, right as the sun set.

Two-Bit:
You were having the worst day ever, and called to tell your boyfriend of three years. In about an hour he showed up at your house with a box donuts. The two of you sat down at your counter. You opened the box and got wide eyed. He pulled a ring out of his pocket and grinned his goofy grin.

Steve:
You guys had been dating for awhile, so he saved up his money to take you on a cruise. You were just having fun and talking as you walked around. He suddenly stopped you and asked you to be his forever, in front of a large crowd.

Dallas:
You guys got tired of Tulsa, so you snuck off to New York around Christmas time. You were walking and playing in the snow when suddenly he asked you to elope with him. He had nothing planned and no ring, but you said yes.

Soda:
For his birthday, the two of you decide to carve pumpkins since it's almost Halloween. You sit on opposite ends of the table so you can surprise each other.
You work hard on yours, carving out a heart and his name. When you both turn your pumpkins around, you get wide eyed seeing his pumpkin said, "Will you marry me?"
He got down on knee and proposed, and of course you said yes.

Johnny:
The two of you were decorating the Christmas tree in your new house together. When you were finished he pulled out the last one. You tried to hang it up, but he stopped you. He opened it and  got down on one knee.

Curly:
It was Christmas and you spent the night at his house. You had given him his present, but he refused to give you yours I until later. That night, he took you for a walk and got down on one knee. "Merry Christmas, babydoll. Will you give me the greatest present of all and he my wife?"

Ponyboy:
You and Pony both loved reading, and one day he decided to buy you your favorite romance novel. He set it out on the counter like this. When the pages are unfolded, the chapter says, "The Biggest Commitment."