The Characters
Lindsay Peck (24)
(Again) Think Jo March of Little Women meets Molly from Booksmart. She’s headstrong. She’s independent. She might not want to admit it, but she’s looking for validation from other people.
Lindsay is a promising young bachelorette who can’t wait to fix you. Right, except, she’s not really ready to admit about the bachelorette part yet because she swears if she can only string the right words together, she can get Colin back if given the chance to do so.
When there’s nothing to control in life, Lindsay finds something to control. At her kindergarten graduation her teacher asked her what she was going to be when she grew up, and she looked out at the audience of parents and said, “I want to be king”. You heard her, not queen, king. When asked why, she said, “So I can tell people what to do”.
Her bluntness may have been cut back through her years of perfecting her social presence, but on the inside she knows when she has a goal, she can get to the finish line. Always with the next step planned, this whole time travel thing isn’t working out all too well for Lindsay.
Not only is she caught in the nightmare of a break up, but she has to get through it in a world she has to figure out how to live in and now she also has to prevent Romeo and off brand Juliet from kicking the bucket. Well, she doesn’t have to. But if she doesn’t, who else will? If only
these 1590s fools would listen to her…
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Casting Inspiration: Haley Lu Richardson
William Shakespeare (31)
Nick from New Girl meets another Jo March type but this time sprinkle in some Jim from The Office. He’s ~complex~. He’s the type of guy whom you might find walking through the woods for inspiration and then getting upset and frustrated because it’s-not-working-but-it-worked-for-others-so-why-isn’t-it-working-for-me?
William is one of the characters who changes from timeline to timeline, but he stays a man in his early thirties who has the same personality in each time. William isn’t the most emotionally aware person in the group therapy session. He’s not great at thinking in the long term because making decisions one by one is easier for him, but he can’t always refuse the chance to do nothing, as that might be the easiest way out.
In following episodes, Lindsay will be drawn to him for his ability to establish an immediate relationship with her, but the frustration comes when she realizes she has to reevaluate how she connects emotionally with him each time, because boy is he a tough cookie to crack there.
Ever the independent soul, if William didn’t feel a pang of loneliness, perhaps he would be single forever, but he sees something in Lindsay that he is always drawn to. Call it star-crossed, but they always end up working together.
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Casting Inspiration: Tom Hiddleston
James (65)
James is Atticus Finch meeting Dumbledore in a comedy club. He loves to laugh and loves people, but he’s got a strong moral compass and is deeply set in realism. He wants to help others. He works in the bar, so he gets the gossip from around town.
James' is sort of an emotional support for everyone around him. He looks at Lindsay as someone he can take under his wing, but because she’s like an anxiety-ridden baby bird, he has trouble holding her there. He’s sort of like everyone’s dad.
If James took the Enneagram test, he’d be a 1 for sure. And even though he’s older, he gives off a young and able energy. No one stops him from helping anyone because he’s old, but if they tried, he might get upset for one of the only times in his life just to shut that down.
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Casting Inspiration: Bryan Cranston
Romeo (25)
Romeo is very prideful and stubborn but also a little dumb. Think a himbo like Jason Mendoza from The Good Place meets the entitlement and gusto of Gaston from Beauty and the Beast.
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Outwardly, Romeo is a bit of a player, but internally, he struggles with wanting to help with bigger issues in the plot.
He likes to think that he can do anything he puts his mind to without help from others, and when he finds that he cannot, he goes through lows that involve him becoming very lazy and moving to the metaphorical couch, losing faith in himself and the situation.
Romeo wants to feel valuable to society, but more so, he wants to feel valuable to others and to the woman he loves. He feels his self-worth is directly tied to his actions and accomplishments and how well he does them. In this first episode, he’s not shown off as much, but his character will be fleshed out much better in future episodes with future versions of his character.
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Casting Inspiration: Roshon Fegan
Joyce (23)
Piglet from Winnie the Pooh meets Alice from Alice in Wonderland. She’s the kind of character that will go down with the ship each time, because her loyalty is all she has to hang onto. She becomes competitive and arrogant when stressed. She has all the patience in the world, but that doesn’t stop her from being able to be sassy. But honestly, that sassiness scares her a little bit, almost like each time she stands up for herself it’s a front.
Joyce is drawn to Lindsay each time they meet because she has a want to be progressive in her heart, but she stops herself because of her surroundings. She refuses to be a product of her time, even though she kind of is.
At her heart, Joyce is very loving. She would love for everyone to just get along. She’s what you imagine your childhood teddy bear feels because they’re always there for you. And she will always be there for Lindsay. Or Romeo. Or anyone who depends on her. Because maybe then she will find that she can depend on them too. Maybe.
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Casting Inspiration: Helena Howard
Colin (24)
Oh boy. Definitely not based exactly off of and quoted directly from my ex.
Colin is a confused young man. When he loves, he loves with his whole being. Entirely. Fully. But the problem arises when he finds himself dependent on Lindsay for validation in his life.
So who is he? He doesn’t even know. He breaks up with Lindsay because he needs to ~find himself~ but he does so in such a sloppy and broken way that it sends her in a spiral.
Across the timelines, he shows up, and he always has an immediate attraction to Lindsay, but when they come to know one another, they’ll find that they will always be meant to be friends and that’s it. And it’s true. Their friendship is so incredibly strong and supportive. By the end of the season, Lindsay realizes this.
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Casting Inspiration: Justice Smith
Anne (39)
Anne Hathaway is a strong independent woman who doesn’t need a man in her life. Yet she’s married to William Shakespeare.
She’s got the attractive nature of Princess Diana and the confidence and boldness of AOC. Yet she has a soft spot. I’m thinking Meg from Little Women. She wants to be
in love. She always has. But sometimes, you have to pull yourself up by your bootstraps when you find yourself in a marriage that lacks the attentiveness you imagined.
Poor Anne.
Throughout the season, different versions of her show off her more forward side, but she remains strong and steadfast throughout.
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Casting Inspiration: Cobie Smulders
The Drunkard/Drifter (35)
What else can be said than what is implied by the name? The Drunkard/Drifter sits around for comedic effect, but he is so much more.
He has an oddly knowing and settling aura about him, like with a word he could deescalate any situation. In every timeline he’s portrayed a drunk or some kind of unmotivated bystander role.
He doesn’t appear to have a great memory because he is often intoxicated or out of it somehow, but it’s hinted that he knows Lindsay and that he recognizes her each time she jumps to a new time.
The Drunkard/Drifter is somewhat of a wise old man, but this wisdom is not often expressed due to him not being a person Lindsay feels she can talk to, a product of her own judgements.
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Casting Inspiration: Robert Sheehan
