Lizzie Borden
Liz, as she prefers to be called, is a classy lady. She will require that you take your shoes off upon entering. Bring her chocolate, she loves that. The two of you will then sip tea, (her favorite drink), and talk excitedly about the upcoming Presidential election, in which Benjamin Harrison will take on (and eventually lose to) New York's Grover Cleveland. She may speculate at the possibility that Grover Cleveland could become the first President to be elected to two non-consecutive terms. It will be quite interesting, she'll say. At the end of the date she'll murder you with an axe.
Mark David Chapman
This date will end quickly after he finds out you're not important.
Charles Manson
Your date with Mr. Manson will be a complete surprise to you when instead of showing up personally, he sends a bunch of his friends in his place. Dinner will be ruined when they mutilate your food. Hey! That steak wasn't cheap! But thats ok, you love that Beatles song they keep singing. The date ends when they write weird things on the wall with your blood.
Jack the Ripper
No one knows for sure who Jack the Ripper was, but many speculate that he could have been a doctor or someone with anatomical knowledge. The point is, regardless of his identity, he is from England. This means he is classy. He may whisk you away to a theatre to see a play converted from one of Charles Dickens many novels. Afterwards, the two of you will walk romantically along the Thames river, make casual small talk, look at Big Ben, parliament, etc. Maybe you can stop in at a pub for a pint! Oh, Jack the Ripper, you are at heart, a romantic. When you get back to Whitechapel, he will strangle you and remove your organs.
Lee Harvey Oswald
This date will be quiet, because, (and you'll find out), Mr. Oswald is a quiet man. He doesn't talk much, but you can tell that he is very smart. Maybe the two of you can discuss your favorite aspects of Russian history. You see, Mr. Oswald lived in the then Soviet Union for quite some time. Don't get into a politics argument with him though! Mr. Oswald is a Marxist! That's ok, he's very polite about it. At some point during the date, he'll excuse himself to use the restroom, which is located on the second floor of his home, behind you. You'll be angry at him for shooting you, but also realize that it is almost mathematically and statistically impossible for him to have committed the crime given his location in the home in relation to yours! You begin to ponder conspiracy theories but it doesn't matter; you're dead.