This is a storytelling challenge. I have essentially laid out a suggested plot, feel free to deviate if you want! The point is to play a very Hallmark movie-esque story as we get closer to Christmas. Play up the cheesiness and heartwarming moments! Once the setup is complete, you’ll be playing different events each sim week. Some weeks may require you to switch active households. The goal is to grow a heartwarming relationship and create a lovely Christmas for all the characters.

Rules
-No money cheats except where prompted in the story.
-Set aging to Long or turn it off for this challenge.
-Start in Fall.
-Set seasons to 4 weeks. This is intended to be an 8 week challenge.
-Delete all holidays except Harvestfest/Thanksgiving and Winterfest/Christmas.

Setup

You’ll need to make two households for this challenge, or download the ones I set up and put on the Gallery:

City Slickers
A couple who are engaged. Person A and B met in University. Person B felt pressured to marry Person A because Person A is likely to be successful/rich in the future. A very yuppie couple. Feel free to make any extended family, especially if you feel the pressure to marry is coming from family. Have them live in an urban world, ex. San Myshuno. For the rest of the challenge description, when I say “SM” I mean the urban world.

Person A (YA):
-Business career
-Hotheaded, Ambitious, (any)

Person B (YA):
-Journalist career
-Family Oriented, Foodie, (any)

Cozy Country
A widow(er) and their child. The parent married their high school sweetheart very young and had one child. Their love was taken tragically too soon. They are committed to raising their child the best they can. They haven’t really thought about love since their spouse died. The child is a sweet kid who means well. Overall, they just want to be a good kid and have fun. Feel free to make the parent's parents and deceased spouse if you want the challenge or headstone for realism. Feel free to make any pets as appropriate. Have them live in a rural world, ex. Chestnut Ridge or Henford on Bagley. For the rest of the challenge description, when I say “CR” I mean the rural world.

Person D (YA):
-No formal career. May garden, raise livestock or horses, or other country hobbies for income.
-Gloomy, Loves the Outdoors, Romantic

Person D (C):
-Creative

Weekly Challenges
1. Country Assignment
-B has been sent to cover the fair in a country town. Move B into a rental property in CR.
-B has to eat at public places (restaurants, bar, food stands, etc.) during this week. They don’t have kitchen supplies at the rental.
-B should meet and learn the careers and all traits of at least three locals during their trip, not including C.
-B should meet C and do an interview with them. C is participating in a fair competition (ex. Prize vegetables, horse competition, prize livestock) and is likely to win. B and C should get the bar at least halfway to friends status during this interview.
-B should take a picture of C and their prize winning something for the article.
-B needs to write and submit her article. Have them write a short story and publish it.

2. Straining Relationship
-B goes home to A.
-Have A throw themselves into work. Try to gain at least one promotion this week. Do daily tasks every day.
-Have B start planning the wedding (or pretend if you don’t have the wedding pack. Visit possible venues, practice making cakes, etc.). A is unavailable to help at all.
-Invite A's boss and their family for a dinner party. Networking!!! Make B cook the food for the party. B’s hobby is cooking so they won’t mind, right? Earn gold on the dinner party.
-Have A and B get into a fight. Children, finances, in-laws, whatever - preferably something that really should be figured out before marriage.

3. Field Trip to the City
-Switch active households to Cozy Country.
-D’s class is taking a field trip to the city! C volunteers to be a chaperone (in my game, C is trying to prove they can be a good parent on their own). Move them into a rental property in SM along with at least three other children -and one other adult. I’m making the kids into a club so they act more like a group.
-Have C take D and classmates to three places/events across three days. Ex. Arts Center, Myshuno Meadows, and a festival. Stay at each place most of the day or for the entire festival. Focus on doing things with D and their classmates experiencing the city.
-At least one night, have C step out to go to a bar. Have him meet up with B at the bar and hang out. Have them realize they have some feelings for each other. Will they leave it at a few stolen glances? Or do they have a spicy one night stand?

4. Thanksgiving to Remember
-Switch active households back to City Slickers.
-B is questioning their resolve to marry A after their second encounter with C. B stops any further planning for the wedding and tries to avoid talking to A until they sort out their feelings.
-Track how much money B makes this week.
-Host a Harvestfest/Thanksgiving party. Invite extended family, friends, coworkers, etc. The more the merrier. B again needs to cook all the food. Make at least three things - appetizer, grand meal, and dessert.
-Have A and B fight and break up during the party. The messier the better! Try to get at least silver at the party. The food was still delicious, and the guests got a show on top of it!
-At the end of the week B has to move out of the apartment. A’s name is on the lease. Use freerealestate cheat to move B into a starter apartment/house in CR and cheat their money down to what they made this week. B wants a fresh start away from the city. Quit and restart the Journalism career at least one level less since you’re taking a pay cut to leave the city.

5. Building a New Life… and Relationship?
-Switch active households to Cozy Country.
-B called C to tell them they moved away from the city and broke up with their fiancé(e). Have B go meet them to console them. This can lead where it may…
-Have B and C reach Good Friends stage.
-Once B and C are Good Friends, have C invite B over to their house. Formally introduce B and D. Have C serve a meal and sit down as a group to eat (I strongly suggest having D set the table to make that happen).
-Have B and C go on a date. Earn at least silver.
-If at any point A and C are on the same lot, have C introduce themselves. Have B and/or C get into an argument with A if they talk. A believes B cheated on them with C.

6. Bake Sale
-Switch active households to B’s household.
-D mentioned during dinner that her class was hosting a bake sale fundraiser for the Christmas festival. B volunteers to help out to try and build a better relationship with D.
-B should try to raise their baking skill level to at least 3 alone.
-Have B invite D to their house. Bake three treats with D. Sell the baked goods with the Home Chef stand, retail store, or set them outside and cheat B some money. Give the money to D using the gift simoleons interaction. Take a photo of your baked goods and write a feel-good article (short story) to generate excitement for the Christmas festival.
-Set up a Christmas festival lot and go to it with C and D. Try to raise B’s relationship with both, but especially D.
-Take a few photos at the Christmas festival. Write another article (short story) about how the festival was for the local paper.

7. Christmas
-It’s finally here. Christmas week! Switch households back to Cozy Country.
-C is trying to set up the perfect Christmas for D and B. Make sure the house is decorated and have a present for D. C already has an idea of what to get B…
-Have C take a Christmas photo of D.
-If you made any of B’s family have C try and introduce themselves. Have C try to make a good impression.
-Have C host a party on Christmas. Invite B and any family you made for the two of them.
-Have C propose to B. Make sure to take a super cute engagement picture!

8. (Bonus) New Year, New Beginnings
-Have B and C plan their wedding. Make D a flower girl/ring bearer.
-For an additional challenge, try to set A up with someone new. They weren’t evil, just not right for B. Maybe invite them to the wedding for some drama!
-Move any extended family you made B and C onto their property. They realized the importance of family.