Mistakes were Made
Harry dragged himself out of bed, incoherently begged a hangover cure off of one of his dormmates, and made his way to get ready for the day.
When he eventually came back from the bathroom, he found the dorm empty and an oddly large black owl pecking at his window. Harry didn’t ponder why the owl was there instead of the great hall at 9 in the morning, which was his first mistake. His second mistake was opening the window and watching the owl fly away after taking the letter. His third mistake was opening the letter, which contained the following message for Harry’s still slightly incoherent mind,
Dear Harry Potter, I hope you receive this letter well as you wake. I was completely unaware of your feelings until you sent that letter to me last night. I have to say, I'm quite flattered.
Wait, what? Harry paused his reading to think. Last night, his housemates had convinced him to do something, what was it again? Something about sending a letter, but to who and what about?
It was a moment more before Harry connected the dots. They had convinced him to send a confession letter to Ginny and he had actually done it. Was this her? Had she responded? A small voice in his head said that it wasn’t her handwriting but he disregarded it as he continued to read.
It must have taken much courage to admit such a thing, what inspired you so, I wonder? Was it that pesky Gryffindor bravery, liquid courage? I assume the latter because of the fumes practically drowning the, what shall I call it? A love letter? Nevertheless, I have included a copy, in case you have forgotten. I find it quite impressive you managed to send it so far while intoxicated, but they do say some people are the truest they can be when they are ‘drunk’. But I have taken much of your precious time. I await your response with bated breath.
Harry was slowly becoming less convinced he had sent it to Ginny the more he read, he knew the spell his housemates had given him could go far but if he didn’t send it to Ginny, then who? The spell was made to send letters to those who you are most attracted to in every way, so who else other than her? He continued to the end of the letter.
With Love,
Tom Riddle, AKA You-Know-Who.
Harry decided then and there, that it was a future Harry problem and he would worry about it later.
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Though he did end up reading the original letter he had sent to Voldemort, or did he prefer Tom? Either way, Harry didn’t want to respond, but after a week of no reply, the other man seemed to take it as a challenge! He started showering him in extremely thoughtful gifts, good advice, and his favorite sweets! How did Tom Riddle know his favorite sweets!?
Except, when he did respond, he did it drunk, Again. At first, it wasn’t bad, a curt sarcastic response, but as he started to get more intoxicated, he revised it. In the reply he sent, he had started flirting with the dark lord and thanked him for all of the amazing gifts, because of course he did. He wanted to drop dead when he found the same black owl at his window with another letter.
Tom had, of course, seen this as a go-ahead to up the ante, and after another week of presents, and flirting, he asked him out on a date. Somehow, his dormmates were convinced it was Ginny doing all of it and pressured him into accepting, and the insanity of it all he did.
That’s how he ended up with a date with his sworn enemy, the Dark Lord, Tom Riddle.