(Note: The bar scene events are from MoonlightAtDusk's fic, "Where is My Mind".)

If there was one thing that Miles Hollingsworth III could never turn down, it was a challenge.

Esme Song was not only just that, but she raised the bar when it came to living on the edge and Miles relished it. If it was one thing that both Maya and Tristan had in common was that they played it too safe. His ex-girlfriend didn't care that the gun that he pointed at Zig's head was a fake. His ex-boyfriend didn't believe that the weed habit was under control and instead he actually had the gall of ambushing him with a damn intervention. No, Esme not only embraced his recklessness but encouraged him to push his boundaries into chaos while laughing at it in her charming way as if it was nothing at all.

Sure there were times he wanted to dial it back. He felt pangs of guilt whenever he caught Frankie in the outskirts of his field of vision staring at him with a worried look on her face. She knew that something was going on. But the lesson of crossing him was painfully learned the last time she and Hunter had decided to meddle. Tristan didn't survive the chopping block and he was no longer a part of Miles' life. One more wrong move and then herself, Hunter or even Winston were at risk of joining him in exile.

But whenever his conscience was strong enough to convince him to scale things back a notch or two, Esme always knew how to push his buttons and fan the flames to reel him back in.

"Don't be such a square."

That was exactly the remark in her haughty tone that propelled him to embark on their latest adventure at the Trap Door. He may not have had any ID, but that did not stop him from diving over the bar and grabbing a bottle of whiskey while Esme was flirting with the bartender. High out of their minds, they danced for hours. And when she was being cold because he pissed her off, she decided to cut his intake for the night and head home. That was when he sought out to hold on to his high elsewhere. It didn't take long before he found a source, and all he had to so was say yes when the stranger in the bathroom asked if he wanted to have a good time. He didn't think twice as he dropped his pants and the mystery man popped a foreign cocktail of pills in his mouth. The rest of the night ended in a blur which resolved in waking up in the woods right next to school grounds with only his boxers remaining on his bottom half.

Such an unsavoury adventure still wasn't enough to stop him from looking for other ways to cut loose. He thought he'd start the day with a couple of enchiladas with Esme in tow, but Tiny had other plans. Miles had no recollection of sending said nudes, but there was no reason why there shouldn't be an encore. In his current lucid state of mind, it was the only thing that made sense. But being the idiot that he was, he tripped over his own two feet and fell head first against the cold, unforgiving ground. The pain was enough to cause him to pass out, but before his world turned black, he heard Esme's oh-so-familiar laughter. Yet it was far from charming. Hearing someone finding joy in another person's agony was monstrous.

Now here he was lying in a hospital bed with a wad of gauze pasted on his forehead to cover the stitches. He could hear his mother's heels clicking across the hall while she paced in front of the door. Unable to distract himself with mindless gaming apps on his phone that was out of reach, Miles had no choice but to think about where his actions have led him. And how he was far from being happy. Wrecking havoc with Esme was just a smoke screen to hide how messed up his life really was. It was actually those who were present at the intervention who had cared for him then and still care now. Well, all but one. Maybe it wasn't too late to change his ways.

The time had come to make things square with all the people that he had hurt before they decided to turn their backs on him for good.