Theodore found the game that was often played between Pansy and himself challenging and Theodore as most males often were, was that of a competitive sort. It was within reach, he likely got tired and grew bored rather quickly, but when it was just out of reach, he never seemed to be able to give up and Pansy was one of those girls that always seemed 'out of reach', not that he wasn't confident enough to bag one of those girls, he had bagged plenty of those sorts of girls up until the news that his parents had placed him indefinitely with Pansy.
Now if Theodore had ever said he had never thought of Pansy in any sort of romantic or sexual sense, he'd be a liar. Theodore prided himself on being one of the most honest people that was known, even if the truth hurt. If you couldn't handle the truth, you shouldn't have came looking for Theodore to start with, that was just how he was. Theodore had thought of Pansy in such ways when she was frolicking about with Draco but such feelings had ceased due to his personal dislike of Draco. Now, Draco had really dug himself and his entire family into a hole all of their own, their social stature amongst the wizarding world had dropped to where they now stood equal to the likes of the Weasleys. Even with wealth, you can't buy your way up the social ladder, not when you've failed as a Death Eater and then went traitor, leading the very thing one had always fought against.
Now if anyone spoke of Draco, nothing respectable came along with the name, instead he was merely more of a joke than he had been before all of this political junk had ensued.
Draco now was at the top of the social ladder amongst Slytherin but when their inner circle went for guidance from a new leader, Theodore hadn't wanted a part of him. Sure, he could have stepped up and guided the blind, became the so called 'prince' but Theodore hadn't ever wanted that and he had always made that clear to everyone, only now, he not only was at the top of the ladder, he now had the female to go along with it. Sure, Pansy played games, he had learned to play along and enjoy every moment of it. She certainly kept him on his toes, a quality that Theodore liked as there was never a dull moment between them.
"I know you're not like the others, why do you think I'm so over-joyed that my parents picked you? I'm certainly not like the others and that in itself is a well thought out match. We certainly don't need public displays of whoreish-ness to prove anything as we've always been above that sort of thing."
Theodore reached out and took Pansy's hand in his own and led her back to the window ledge, sitting down and placing her on his lap in a seated position. He knew she'd likely not remain there, and he'd perhaps get the usual death threat or Pansy's infamous glare of doom, none the less, he thought that look and the threats were amusing and well, Pansy made it look better than anyone else ever could.
"Humor me for a moment, my lovely wealthy widow. What do you want to do after schooling? Not what your parents want, but more so what you want?" It was an honest enough question in it's own right.
"And will you be doing such before or after my untimely death with tainted tea?"