Immediately following his traumatizing experience in the staff room, Riddle came to the realization that perhaps a date with McGonagall could lead to unforeseen benefits. He knew that there were plenty of talented witches, very likely with purer blood, who would be easier to convince to join his movement, but McGonagall was quite the tempting prospect in multiple respects. Firstly, he knew from their school days that she was a truly remarkable witch; he had been in the sixth year NEWT transfiguration class a year early and she had been his only real competition. Clearly a woman who made Lord Voldemort work to keep his place at the top of the class was valuable.
Another crucial point in his conquest was that it would strike a significant blow to the damnably omniscient fool, Dumbledore. He had consistently been the professor to whom she had turned to for help, not just in transfiguration, but in other more personal matters as well. The fact that he hired her so quickly was ample proof of his fondness for her, rather akin to Dippet's for Riddle himself. Furthermore, when brought completely completely into hiis own allegiance, McGonagall could serve as a most excellent spy on his behalf, as Dumbledore would be loathe to believe his favorite student capable of such blatant treachery.
And finally, she had worked with the Ministry for some time. Clearly she was disillusioned, or she wouldn't seek a lower-paying job after title and position without a very good reason.
"Yes, it's pretty much foolproof," he said aloud, "although timeframe remains to be seen." And filled with his familiar sense of smug complacency, Riddle retired for the night.
The weekend arrived quickly, but not quickly enough for eager students hoping to start Christmas shopping early in the month. As one of the adult escorts, Riddle was required to assist with checking the students for banned items, upon exiting and entering the castle. After a straggling Ravenclaw third year, who seemed to think Probity Probes a foreign and hilarious concept spent a quarter hour dodging one, was successfully dispatched, Riddle had a few moments left to plot before his date with McGonagall. Lousy Ravenclaw kid was probably a mudblood.
He recalled that she had mentioned she was staying at the Hog's Head for the duration, as Hogwarts was rather far from her native part of Scotland. Note to self: Do not confuse her with the Irish. He preferred his face as it was. Perhaps he would pick her up there and improvise, since he hadn't actually told her to meet him anywhere and she hadn't seemed overtly eager. The appearance of sincerity, Riddle realized, was crucial, and he became more aware of his inability to make a planned event seem spontaneous. Interaction with Dumbledore was ample proof of his inadequacy in that area. Not to mention he hadn't been in the dating sphere for the past five years since he'd gone underground…he hoped he wasn't out of practice.
Accurséd romance. A foreign concept, but he'd have to make it work.
As he walked, a ways behind the other teacher chaperones, he tried to dredge up what little he knew about her from their interaction at Hogwarts, nothing very useful coming to mind. He cursed quietly. Passerby would have seen a young man, head bowed, grumbling to himself in a way that wasn't strictly sane. Try again. She was in dueling club, on the Quidditch team... he may have danced with her a couple of times at the Slug Club parties... Nothing particularly useful came to mind. He felt rather inclined to capitalize on what little remnants of a school crush remained, if there were any.
Ah well. Conjuring a bouquet of roses got him two horcruxes, so it was proven to be effective. It was worth a shot again. It was a shameless cop-out, he knew, but what else could he do?
He arrived at the Hog's Head and entered, shaking snow off his cloak. He looked around the room searchingly, until McGonagall entered his line of sight. As he walked over to meet her, he was painfully aware of Slughorn, oak matured mead in hand, following his gaze and then brazenly grinning at him with a humiliating lack of subtlety; it wasn't exactly diverting anyone's attention. Cursing McGonagall for being a brilliant witch and thus rendering her services necessary, himself for subjecting himself to this masochistic torture, and Slughorn for loudly whispering to the barman complete with illustrative gestures, Riddle reached her after a walk of shame that seemed altogether too long.
He offered her his arm. "You look nice," he murmured quietly, lest someone other than McGonagall hear him. Slughorn's not getting any crystallized pineapple this Christmas. My mind is made up. He meant it, as well. Her hair was twisted up into a French knot, and she was wearing very airy, sage green cashmere robes. The gust of cold air the open door allowed in brought a pink flush to her face.
"Likewise," she said, glancing over him. "Amazing what a difference leaving that precious catalogue behind makes," she added, taking his arm.
Riddle's face soured at the comment. For a moment he considered laughing loudly, announcing "now Minerva, not here, can't you wait? It hasn't even been five minutes!" but stopped once he considered potential effects on his reputation, instead saying, "Shall we?" quietly and walking with her to the door. Slughorn elbowed him as he left, eyebrows performing a bizarre tumbling routine of suggestion. Riddle repressed the urge to hex Slughorn, Obliviate the rubberneck bartender, and apparate away to Albania. To make matters worse, McGonagall seemed to be aware that he was up to something, or at least noticed he wasn't calm, and delighted in his discomfort. Her little smile certainly couldn't only be because of the Christmas tree she was looking at.
It wasn't too late to escape to Albania...
He composed himself once outside, pausing once they were no longer visible to Hog's Head patrons. "I brought you flowers," he said quietly, conjuring a bouquet of roses.
Hell, it worked before. Why not again?
"Very pretty," she said, lifting them to inhale their fragrance. Riddle, not averse to invading people's minds, gathered that her favorite flowers were hyacinth, so as the blooms reached her nose, he transfigured them. Yes, he was showing off.
"Nice," she said, beginning to smile. "But I'm afraid they have the texture of rose petals." She smirked at his disbelief. "No matter, Tom, transfiguration isn't really your specialty, although for a nonverbal it was rather good. How did you know these were my favorite flowers?"
Occlumency isn't really your specialty... Riddle thought snidely. "Shall I say intuition? They suit you," he said instead.
"Intuition for a mundane detail like that?" She raised her eyebrows. "I find that...creepish."
"I think the word you meant to say was 'sweet' or perhaps 'unusual.'" Riddle replied. "Did you have any place in mind?" He asked, changing the subject.
"Personally I'd rather revisit Hogwarts, but you'll need to escort students back, right?" He nodded. "Then let's just tour Hogsmeade and catch up."
"We can see Hogwarts afterwards if you like, but you'd be wasting all of your Saturday on me," he said, fixing his eyes on her intently. Cheesy, but tolerable.
"Well, I'm about to waste half, so what does the rest matter? I'll see the school again, at least, even if I don't have a tour guide of my choice." She took his arm without invitation this time. "So how do you find teaching?..."
They continued for the rest of the date in this manner, stopping for a coffee along the way. McGonagall, Riddle decided, was like a cat. Not just any cat; a tabby cat that would pretend to be placid and trusting, but really, once it entered your home it would take over so that even the tea had cat hair in it, and the cat would be judging you all the while, as if it were your fault.
Riddle did not like cats; they were far too independent as pets and he couldn't really talk to them. If not a snake, a subservient dog would be his animal of choice. And it just added to the irony that McGonagall was on the list of recently certified animagi, and a cat at that. As if his life wasn't trying enough.
Dumbledore's name came up in the conversation frequently when it strayed toward transfiguration, eliciting complementary remarks from McGonagall and irritation on Riddle's part. Clearly, she was heavily influenced by her Transfiguration mentor. "Now Tom," McGonagall said suddenly, "Discussing magical theory is as enjoyable as ever, but you've hardly told me anything of what you've done since school."
"Unlike you, I haven't had the most interesting of jobs, but I could bore you with details of artifacts from Borgin and Burke's should you so desire.."
"Really. You and I both know you aren't one to let your mind idle. I doubt it's physically possible for you." Riddle chuckled.
"Ah, Minerva. You always were so astute." To the point of being insufferable. "But I simply can't help it if your life is more interesting than mine. And that was a rather mundane detail to remember about me, wasn't it?"
She laughed. "I suppose so. And do you find me creepish now?"
"Certainly not. I don't think it's physically possible for you." Smooth.
She smiled and pushed him playfully. "I'll remember that and take full advantage of it later."
"Please do, and don't leave me out of the equation." Riddle replied with what he knew was rather obvious flirting.
They continued on in companionable silence, following the homeward bound group of students to the gates of Hogwarts, where Riddle was forced to endure what seemed like an eternity of checking students for banned items. Confiscating love potions, dungbombs, and giant firecrackers was stressful enough, and Slughorn wasn't helping, with his booming declarations of "love in the air" and "you're a very lucky man, Tom" and the like. A request for him to lower his voice from the "smitten" gentleman in question resulted in a low, constant stream of incessant prattle that was significantly worse, causing his chins and mustache to quiver in a most repulsive manner. It was rather disgusting.
Despite the less than stellar events of the day, Riddle was pleased to see Dumbledore's surprise at the image of Riddle and McGonagall walking closer than strictly necessary across the darkening grounds as he left her at the gate.
"I leave on Monday. I think I can safely say I enjoyed myself, and I'll be sorry to leave." McGonagall said, turning to face him at the gate.
"I'm glad to hear it, because starting next year, this will be every weekend." She smiled.
"A bit presumptuous, aren't you?" She pressed a kiss to his cheek. "Good night."
"Can you really blame me? And you've all but said yes." He raised her hand to his lips. "Good night, Minerva." He was clearly off to a glorious start. "Perhaps I'll see you during a break."
"Hopefully. But like you said, there's still next year."
En route to the Great Hall, he was accosted by Slughorn. "Tom, old boy, would it be premature of me to congratulate you?"
Tom raised an eyebrow. "Whatever for, Professor?"
Slughorn chuckled. "I've been around a while Tom, and I can see things. That girl is so besotted, you're a fool to play dumb. Not to mention you aren't convincing anyone with that 'aloof' act. I can tell you aren't immune to Minerva either. Who could blame you? She's very pretty, Tom..." Way to completely misread the situation, Slughorn.
"I assure you, I just wanted to catch up." Annoying though Slughorn may be, Riddle was secretly pleased. Slughorn's erroneous interpretation proved he was quite the actor.
Slughorn winked. "I won't say anything! But I'm glad this clears up those rumors about...well. Everyone has quirks Tom, but are those catalogues really necessary? People were starting to wonder."
Tom pinched the bridge of his nose in frustration. "Those rumors were completely unfounded. I'm happily single. Why does everyone think it means something?"
"I feel inclined to disagree with 'happily single'," Slughorn said, beaming. "What a loss to women everywhere. You know, I was just telling Scamander.."
Will he ever shut up? And as far as the catalogue, this settled it. He'd charm the books to look like Magical Law for Beginners or perhaps an encyclopedia. Let's see who questioned his reading material now.