Because men have been trashboys throughout time.
Going into the date, I know that Paul Revere works as silversmith as his day job (because obviously it's really hard to monetize being a Founding Father). I will romanticize this and tell him over and over that I think it's cool that he is COMPETENT. But it will turn out he went to Brown to study silversmithing and built surreal asymmetrical sets for a production of "Hamletmachine." Late in the evening we'll go to Paul's studio and I’ll have him engrave me a silver baptism cup with the words "Teen Witch." I will consider the night a success but when I try to take it to the next level, he will freak out and stop answering my texts.
I’m first attracted to Napoleon because I think a short guy might be more open-minded to dating someone with looks that veer from traditional beauty standards. His intense belief in himself inspires me to believe in the worth of my own ideas, so I stop constantly writing down a joke, deciding it's stupid, and questioning every life choice I’ve made for the past six years. But pretty soon he realizes that the extreme drive I claim to have clashes with the way I regularly spend five hours watching “Pretty Little Liars” and then another five hours reading fan theories about it on the Internet. He calls it off, and a year later, marries a girl who’s not only shorter than him, but also extremely petite, so he doesn’t have to use his experience with height discrimination to love her despite her nontraditional beauty. He just feels big and powerful in comparison.
I will be really excited for this date because Ben Franklin is my exact "type": a funny guy who is more successful as a writer and confident but not actually attractive. I will feel like I'm in a power couple, which I crave because I'm a female Sagittarius. If things go well, I imagine he will give my career a boost and I'll achieve my dream of having people gossip that I'm only where I am today because i abused my sex appeal. But the date will go south almost immediately because he will not be able to stop riffing and anytime he says something funny he’ll immediately tweet it. I'll steer the conversation towards a discussion of Hillary vs. Bernie Sanders but it will quickly become clear he doesn't understand politics beyond what he can express in a one-liner. By the end of the night I’ll realize it's not even worth it to make out with him to confirm that I am desirable and just go home.
After a string of awful Tinder dates with investment bankers, I’ll be immediately taken with Robespierre’s speech about income inequality at the bar after our mutual friend’s improv show. I’ll feel refreshed to find someone who shares my values, and ignore that he lives off a trust fund and can’t handle his opinion being challenged. One day a few months later, he’ll mention he thinks it's pointless for women to try to get rights in the current political system instead of just overthrowing the whole thing. We’ll argue to the point that he yells, “When you’re like this it makes me want to cut your head off." I’ll be like, “Whoa,” and he’ll be like, “I'm sorry, that was too far, I don’t want to cut your head off for disagreeing with me. It’s just an expression." And I’ll be like, “Is it?” Then he’ll give me a piece of vegan nut cheese, and we’ll start talking about how vegan nut cheese isn’t trying to taste like real cheese. It’s just its own delicious thing.
I will be a little wary of this date because James is serious and doesn’t whittle wooden eggs for creative expression. But it will be the best date I've ever been on. We'll go to the Met and he won't try to teach me about white male artists that I have already clearly stated I know about. Instead, he'll point to a random carving in the antiquities wing that I’ve walked by a thousand times and say, "I think there's this belief that people who lived in the past were somehow not as smart as we are, but if you gave me my whole life to carve that elephant, I couldn't do it." At the bar afterwards, he’ll tell me about how he wrote the entire Constitution while all the other Founding Fathers were getting turnt and I'll be like, "I GET IT. I wrote my Mock Trial team's entire arguments as part of my weird symbiotic friendship with a hot popular kid named Jeff Sprague." We'll hook up and I'll be SO EXCITED and Gchat my best friend about it for two hours afterwards. The next week I'll find out he's dating a girl named Dolley.
Otto von Bismarck
I’ll pursue Bismarck after learning everyone in our freshman dorm reviles him. Feeling misunderstood in my college environment, I’ll hear that he’s a sociopath who only uses people to achieve his own ends, and assume he too must just be misunderstood. My desperate need for any positive attention will drive me to become his closest confidant after he gives me compliments about my writing, even though they are interspersed with insults about my body, and also my writing. Though alienating, his manipulative ways do allow him to quickly gain power, and also have me let him call me “Sugar Tits.” After one too many times being summoned to bring him soup while ill, and then being kicked out when someone he wanted to have sex with was coming over, I’ll decide I’ve had enough. We’ll break off ties, and though when he reaches peak power as Iron Chancellor I’ll sometimes wonder if maybe I should have just Hillary Clinton’d him to the top. I’ll mostly still think it wouldn’t have been worth it.