The first time that Draco asked Hermione Granger out was when they first met at the train station. He first saw her standing there waiting for the train and he thought that she looked lovely with her frizzy bush and rosy cheeks so instead of getting to know her or even asking her name, he walked up to her and asked her out in which Hermione promptly said "No thank you".
The second time that Draco asked Hermione Granger out was in potions class in second year. He knew that she was a mudblood and he knew that he was friends with the boy-who-noone-should-give-a-crap-about but neverless he asked her to go out with him to which she said no to without even looking at him.
The third time was outside at the lake. He saw her reading there and he didnt know why. Maybe tradition but he asked her out and she looked at him like he was crazy and told him to stick his question where the sun didnt shine. Draco was happy. He was making progress. At least she was thinking about his butt.
After her fourth refusal two weeks before the Yule ball, he was even more determined to make her go out with him. Even if he only entitled himself one ask per year.
At his fifth year at Hogwarts, he was scared that his father would find out about him courting a mudblood... even if it was once a year... for like a minute. But he still asked in a whisper in the hall and she whispereed back the same response he got every year, one of refusal.
Sixth year was tense. Voldermort was back and Hermione was busy with the horcruxes and Draco was scared. But even so, when he found her crying at the back of the library one month into school, he put her arms around her and asked her to go out with hi even though part of him hoped that she would say yes for his own greed, but he knew that yes was a better choice to keep hem both safe. Apparently Hermione saw that too and whispered a teary "No thank you, but thanks for trying". Either that or maybe she wasnt ready or didn't like him... but he banished that thought from his mind. After all, he was going to have to do this every year until she said yes so, why stop because of a hairless slimy old man?
It was now seventh year. At graduation. All the students came, even the Slytherins. They had to graduate after all. Draco lived with the shame of even associating with Voldermort and being a Death Eater. But the past was the past and he could do nothing about it. He still havn't asked Hermione her yearly question yet since he was almost always at the manor and her and her nitwitted friends were off saving the world. He felt horrible for not saving her from Bellatrix last year. He just couldn't. His family was everywhere. He just couldn't and even though she still left with scars, she survived and Draco was grateful for the little things. He couldn't bring himself to approach her this year. People would think that he was trying to get into good graces with everyone just for being with part of the people who saved the world. She was laughing across the room and met his eyes and smiled. She excused her self from her friends and started to walk over to Draco. Draco was wondering what was happening and before he knew it, she was in front of him, smiling the cutest most bashful smile he had ever seen anyone have. She then shyly held his hand with both of hers. Now everyone was looking and him. And her. At them. The whole ballroom went quiet and he wondered if she had went completley bonkers. She talked first asking "You havn't asked me this year yet. Why?" everyone was wondering what she was talking about but dracoo could only see hermione. He then whispered " Would you like me to ask?" And she smiled brightly and nodded her head and replied " I was afraid that you wouldnt do it this year. You know what they saw, seventh time the charm". He grinned widely as Hermione giggled nervously and he swept down and proceeded to capture her lips with his.