Judging by her pink cheeks and lowered gaze he'd bet a galleon that she wasn't fine, though he was loathe to push her. Best to tread carefully then. "If you're sure." he said slowly, witholding a frown as he realized he was still holding his pencil and his book aloft on his knee. He slotted the charcoal drawing pencil inside the spine of his cartography book, using it as a makeshift page holder, like he did for basically all of his books before placing it on the sill. He grabbed his meade and took a slow sip, still observing the Ravenclaw that had perched on the ledge with him.
He wasn't sure what about his invitation she'd accepted but he was now curious. She seemed really... doll-like and demure to him and he wasn't sure if that just came naturally or if she was putting up some sort of facade. "Desolate was less gentle than melancholic." he admitted quietly. Trust a Ravenclaw to argue linguistic semantics when describing their general state of being, he thought wryly. She was right, though. Melancholic didn't work if you knew the reason you were sad. Every other description he had seemed invasive and rude, though, and he hadn't wanted to be. "Pretty but sad." he mused deciding that maybe a compliment would lift her spirits, if only a little.
"Yea its just getting started. It gets a bit rowdier the more people indulge in drinks and games, usually." he said, amused, as he flickered a blue eyed gaze towards the Ravenclaw. She was pretty, he could see the allure that had drawn Donnelly in, at least, though he was still incredibly curious. He'd never dated anyone younger than him - they were usually all either his age or older. (Usually older, actually, now that he thought about it.) He didn't like to be put in positions where he held an advantage and it seemed to him the fifth year girls were all a bit... naive he supposed. Gentle and ridiculously pretty, to be sure, but he'd still end up feeling like he was taking advantage somehow. Like Hy, for example, who seemed easily swayed and manipulated. It made him queasy thinking about it, really, and so he'd steered cleared of the 5th year girls as a whole (he'd been completely preoccupied by Orlaith, anyway, so it hadn't mattered).
But he could definitely see the draw. "Yes. To both." he said, a little bit of laughter in his voice as he spoke, and took a peak outside. "Rowdier than this, even. Try not to worry so much about everything. Some people are bound to be miserable no matter how much fun you plan something or how meticulous you are about hosting." he offered, knowing from experience, and having learnt at the hand of his mother. "You've provided the the essentials to a good party anyway. Music, drinks, food, and a healthy boy to girl ratio." he said with a bit of a grin, as he spotted the aforementioned snogging couple take their little tryst inside finally. Took them long enough. He hoped they had some fun. "I always run out of my mothers parties, and those are a blast too. Sometimes its nice to get a breather before you dive in headfirst into the chaos." he added with a bit of a sigh. He wasn't someone that enjoyed being out of control. He liked having his faculties about him and staying sharp and observant. It'd always been like this for him and so it was difficult to give in fully to a party like this.