theodore

Everything below here is optional! The main challenge is only 12 generations, I just couldn’t help myself and ended up adding in a few more songs 🥲 You can challenge yourself to do all the generations, or use these to replace any of the generations you see above.

Basic Rules

Play on any life span you want but I recommend playing on Normal life span.

You are encouraged to play with female heirs. Of course, this is optional!

You are discouraged from using money cheats. Some generations have stories that are related to their social class— so try to stay true to the story as much as you can.

You can live wherever you want unless the generation states otherwise.

Feel free to customize each generation’s race and sexual orientation

Unless specifically stated, each generation has to finish their aspiration and career.

Even if most of these books are classics, I wrote this with a more modern take on it. You don’t need any mods or CC to fit the eras’ aesthetics— but if you want to, you totally can!

⭐ means there’s a recommended mod for this!

☽༓･*˚⁺‧͙

Generation 1: Elizabeth Bennett 📚 Do not consider me now as an elegant female, intending to play you, but as a rational creature, speaking the truth from her heart. 📚

It is a truth, universally acknowledged, that all Sims 4 challenges must start with an heir. In this case, that’s you, which is surprising because everyone else in your life has decided that you are plain, especially when compared to your other two sisters. Lately though, you start to sense that you’ve been getting more attention from your neighbors. One particular Sim hasn’t been able to leave you and your family alone… and you don’t like them at all, not one bit. Well… maybe just a bit.

Aspiration: Successful Lineage 

Traits: Family Oriented, Hot-Headed, Bookworm OR choose/roll for the last trait

Career: Journalist

→ Master the Writing skill. → Live in a rundown family home passed down by your parents with two sisters until you are married. → Have a negative relationship with a neighbor. → Reject a proposal from your work boyfriend. → Build a relationship with your neighbor after you reject the proposal of your ex. → Have a scandal involving one of your sisters that your neighbor supports you through. → Fall in love and marry this neighbor then move in with him. → Have two children.

☽༓･*˚⁺‧͙

Generation 2: Emma Woodhouse 💗  It is very difficult for the prosperous to be humble.  💗

Growing up, you were always the sheltered one. Your father was very protective of you, and therefore never let you out of his sight. Of course, that didn’t stop you from becoming well-loved by the entire town. You were known for throwing the best dinner parties and befriending everyone your father and mother knew. Needless to say, this got to your head a bit. You weren’t arrogant, you were confident. In everyone’s eyes, you could do no wrong. Well, everyone except your childhood best friend— who was never afraid to call you out for being a bit clueless at times. 

Aspiration: Neighborhood Confidante OR Party Animal

Traits: Self-Assured, High Maintenance, Music-Lover OR choose/roll for the last trait

Career: Romance Consultant or Lawyer

→ Master the Charisma and Piano skills. → Host at least 5 gold-star dinners. → Have a childhood best friend who’s a bit older than you. For example: When you’re 17 (end of teenage years), they’re already 20 (start of young adult years). * → You can’t have good friends who are your age until your childhood best friend ages up into a young adult. → Make a new friend that you treat like a “project” until you two fall out. Choose if you two will reconcile in the future. → Profess your love to your childhood best friend during a heated argument. → Marry your best friend and live with your mother and father in your childhood home until your parents die. Have one child. *It goes without saying to only get with your childhood best friend when the two sims are both young adults 🙂 No super uncomfortable age gaps, please.

☽༓･*˚⁺‧͙

Generation 3: Scarlett O’Hara ✨ “Tomorrow, I’ll think of some way to get him back.” ✨ All your life, you grew up spoiled. Your mother and father were so in love, and you almost expected to have a story as romantic and easy as theirs. However, when your high school flame elopes quickly with someone else right after graduation, you start to spiral. No longer able to get things your way, you begin to self-sabotage and jump from relationship to relationship. Deep down you know you should stop and smarten up but frankly, my dear, you don’t give a damn.

Aspiration: Soulmate— you fail this 

Traits: Materialistic, Genius, Jealous OR choose/roll for the last trait

Career: None until your divorce then become a Manual Laborer + Barista

⭐ Recommended Mods: Healthcare Redux Mod, Extreme Violence Mod

→ Don’t master any skill. → Have a high school flame who elopes with someone else. → Elope immediately with someone else. Have them die tragically.* → Marry another person quickly who you have bad compatibility with. Get negative romance with them right before they pass.* → Marry a third time. Have them catch you in a compromising moment with your high school flame, which leads to a divorce that leaves you with nothing. → End up working two part time jobs to keep your household running. → Have 4 kids with your 3 husbands (you can cheat for twins, if you want). *You decide how they die. I recommended having mods like the Healthcare Redux and Extreme Violence in your game for realistic roleplay reasons— but if he gets tragically eaten by a Cowplant that works too! 🙂

☽༓･*˚⁺‧͙

Generation 4: Jo March 🧾 “When the first soreness was over, she could laugh at her poor little book, yet believe in it still, and feel herself the wiser and stronger for the buffeting she had received.” 🧾 Growing up was not easy for you. Your childhood was incredibly unpredictable with your mother jumping from relationship-to-relationship. And when things started to stabilize emotionally, you ended up in poverty.  Luckily, you had your siblings to cling to, and a passion for writing that’s unmatched. You wrote a ton of things across different genres, except for romance which you didn’t quite understand. In fact, everyone always expected you to be a little woman, not rough or wild, but you knew in your heart that’s not what you were destined to become.

Aspiration: Best-Selling Author

Traits: Creative, Unflirty, and Ambitious OR choose/roll for the last trait

Career: Author

⭐ Recommended Mods: Writing Career Overhaul, SNB Banking

→ Master the Writing and Logic skills. → Be best friends with all of your siblings. → Start selling short stories as a teenager to help pay the bills. → Get a best friend in high school who professes their love to you during graduation. Turn them down. Optional: Have them marry one of your other siblings. → Move away to the city to focus on your writing. Always send 30% of your income to your mother until she dies. → Due to a tragedy in the family, adopt a child of one of your siblings.* → Win a Starlight Accolade for one of your novels. → Never marry but live a fulfilling life. *They are to be the next heir to preserve the bloodline. You can adopt more if you want.

☽༓･*˚⁺‧͙

Generation 5: Anne Shirley 📖 “I believe the nicest and sweetest days are not those on which anything very splendid or wonderful or exciting happens but just those that bring simple little pleasures, following one another softly, like pearls slipping off a string.” 📖 You were adopted by your aunt and lived a happy childhood. Despite being surrounded by family drama, you never let it dampen your spirit. You struggled with social cues and caused mayhem wherever you went— of course, that never stopped you from making your voice heard. You were, afterall, raised by someone who was never afraid to make a point. However, unlike your aunt, you always longed for romance. You always imagined big declarations of passion— but perhaps it’s time to learn that love creeps to one's side like an old friend through quiet ways.

Aspiration: Academic OR Soulmate

Traits: Romantic, Socially Awkward, and Loyal OR choose/roll for the last trait

Career: Education Career

⭐ Recommended Mod: Education Overhaul

→ Master the Research and Debate skill. → Have a childhood enemy that you become best friends with in high school. → Go to University and study Language and Literature. → Fall out with your best friend while in University. → Start dating someone you meet in University but break up right after graduation. → Get a job in the Education Career and write on the side. → Reconnect with your former best friend and realize you love them. → Get married to your best friend. → Retire from the Education career and become a freelance writer in your twilight years.

☽༓･*˚⁺‧͙

Generation 6: Nancy Drew 🔍 “I don't promise to forget the mystery, but I know I'll have a marvelous time.”  🔍 Every bedtime, your mother read you stories that she and your grandmother wrote. Among all of those, it’s your grandmother’s mysteries that impacted you the most. There was something so thrilling about being a heroic, fearless woman who helped others out. Because of this, you gained a bunch of friends who loved you very deeply. With their support, you grew up as a well-known detective who can solve any case.  It was a fun life, but you eventually settled down in Henford-On-Bagley to have a family of your own.

Aspiration: Friend of the World 

Traits: Generous, Nosy, and Outgoing OR choose/roll for the last trait

Career: Detective OR  ⭐ Zerbu’s Simvestigations Mod

→ Master the fitness skill. → Be close friends with both your parents. → Have 2 best friends who are either your roommates (Discover University) or live in the same apartment complex as you (For Rent) for your entire YA life. → Get engaged to someone you meet on-the-job. → Before marrying your fiance, go on a trip to Selvadorada with your 2 best friends and explore the Jungle Temples. → Settle down in Henford-On-Bagley and have a farm life of your own. → Never move away once you settle in Henford-On-Bagley.

☽༓･*˚⁺‧͙

Generation 7: Dorothy Gale 🐶 “If we walk far enough, we shall sometime come to someplace.”  🐶 Growing up you knew that there was more to the world than what was outside your own backdoor.  Afterall, your mother was a famous detective— if she went on her own adventures, why can’t you?

With her and your father’s support, you spend your young adult life traveling. You made some great friends along the way (and even some loves), but eventually you start to wonder if there is no place like home.

Aspiration: Local Aspirations— complete at least two

Beach Life

Mt. Komorebi Sightseer 

Fount of Tomarani Knowledge

Traits: Adventurous, Dog Lover, and Loves Outdoors OR choose/roll for the last trait

Career: Any Freelance Career 

⭐ Recommended Mods: SimNation Travel, Home Region

→ Have a dog that goes everywhere with you. → Live in 3 or more worlds during your Young Adult life. → Make 3 best friends that each teach you a valuable life lesson. → After making your three best friends, use reward points to add the following traits: Brave, Savant, and Incredibly Friendly. → As an adult, realize you miss your family and return home. → Have a long distance relationship with the father of your children.

☽༓･*˚⁺‧͙

Generation 8: Wendy Darling 🌟 “She was a lovely lady, with a romantic mind and such a sweet mocking mouth. ”  🌟 You grew up waiting. First, for your father’s seasonal visits… which eventually stops when you become a teenager. Next, for the opportunity to leave Henford-on-Bagley to pursue your dreams of becoming an actress. And finally, for your first love, a man who refused to propose to you, no matter how long you waited for him to. Eventually you grew tired waiting and decided to grow up. You married a sensible man, had a child, and gave up your dreams of becoming an actress. Still, you held on to the dreams of your first love and end up reconnecting in a night of passion that leaves you pregnant with his child. Realizing that he’ll never grow up, you decide to dedicate your life to your family and husband.

Aspiration: Master Actor/Actress - you fail this or the⭐ Housewife Aspiration (after you marry)

Traits: Perfectionist, Proper, and Cheerful OR choose/roll for the last trait

Career: Actor/Actress

→ Master the Parenting skill. → Have a distant family dynamic with your father who never lives with you. → Join the drama club and meet your first love. Optional: He has the childish trait. → Give your first love all of your major romantic milestones. → Lose touch with your first love when you move to Del Sol Valley. → Marry a man you’d consider as sensible. Have one child with him. → Have a one time secret affair that results in another child. → Dedicate your life to your children afterwards.

☽༓･*˚⁺‧͙

Generation 9: Alice Liddell  🐰 “It would be so nice if something made sense for a change.”  🐰

There were times you felt like you never truly belonged anywhere. While everyone at home lived and abided by your parents’ rules, your head was always in the clouds. Sensibilities and propriety were never in your vocabulary, much to the disdain of your father and the rest of your siblings. Still, you were a free spirit that could never be controlled. After moving out as a young adult, you fell in love with cooking and mixology. You also met a group of misfits who were as different as you. Every Sunday, you’d host special “tea” parties with them, that broadened your worldview and made you realize that the world gets curiouser and curiouser with each passing day.

Aspiration: Master Mixologist or Master Chef

Traits: Clumsy, Foodie, and Childish OR choose/roll for the last trait

Career: Culinary Career

⭐ Recommended Mods: Basemental, Grannies Cookbook, Open Love Life

→ Master the Cooking and Mixology Skills. → Have a juice/nectar hobby on the side. → Have a club with people who have weird or eccentric traits.* → Fall in love with someone with the Erratic Trait. → Host “tea” parties every Sunday in your own home. ⭐ Optional: Use the Basemental Mods and have your Sims get high on dope/drunk on alcohol during the tea parties. → Dye your hair a different, brighter color. → Live in a quirky and colorful house. → Befriend a rabbit who you talk to constantly. Name them The Mad Hatter. → ⭐ Optional: Be in a polyamorous relationship with Romantic Boundaries OR the Open Love Life Mod → Have two children. *You decide what weird and eccentric means.

☽༓･*˚⁺‧͙

Generation 10: Countess Ellen Olenska  🎨 “The real loneliness is living among all these people who only ask one to pretend.”  🎨

You appreciated your mother’s lifestyle. You saw the world for what it could become, and not what everyone wanted it to be. However, you worried about your younger sister. You saw her innocence and wanted to protect it. When you turned into a young adult, you moved away and took your sister with you to start anew. However, life was not always easy. Straight out of teenhood, you married someone from a different city and had a tumultuous relationship with him. You separate with him and continue to care for your sister. You’re able to provide for her through your paintings, which also brought you a lot of fame. When she grew up into a Young Adult, she formed an attachment with a man that… intrigued you. She married him. This kept him in your life, but made it difficult for you to ignore your feelings. One night, you find yourself alone together, and you must make a choice: stay with him and break your sister's heart, or leave forever to give them peace. You have a price to pay either way— we can't behave like people in novels without consequence, can we?

Aspiration: Painter Extraordinaire

Traits: Gloomy, Art Lover, and Family Oriented OR choose/roll for the last trait

Career: Critic 

⭐ Recommended Mods: RPO, Wonderful Whims, Custom Relationship Bits, Soulmates