I thank Proxian_Girl for bringing the 'Who's your daddy?' Challenge here-well, what she can remember of it. Then I came up of the idea of making it our own.
So here it goes:

[If something you think is impossible/shouldnt be there, please comment]

Storyline: One day a beutiful woman, fresh out of university [That is optinal] decided she wanted to break the Simcity record for
the most children. Then she decided to have LOTS of lovers- just a crazy thought. But she went out and did it. Guess who let her? YOU.


Rules & Objectives:
- One sim woman should have children by thirty-four different fathers.
- The children are named with al the same letter starting their name.
- The mother CANNOT get married until Child 1 is a child, but MUST do so before Child 14 is born or you cant marry.
- People do not have to be Townies/NPC's.
- Not permitted to move-out husband or deliberately kill him off/divorce him..
- At least one pregnancy must result in twins. (cheats/hacks shouldn't be necessary for this-- It would be too easy within THIRTY FOUR CHILDREN!)
- Service NPCs such as maids/gardeners/exterminators may not be hired, except once to gain them as contacts if you wish to use them as fathers, after which you must dismiss them immediately. Nannies may only be hired by the husband or a teen child, and may only track their schedules.
- If you REALLY want to marry, then no marrying Mister Big/The Diva (?)

For bonuses:
- Multiple alien pregnancies
- Teen alien abductions
- Multiple sets of twins/extra children per father
- Went to collage then started on empty lot.
- No aspiration award items except the Elixer of Life. No nothing that provides mood boosts.
- Tots learn the main toddler skills before aging (nursery rhymes do not count).
- Bonus for a non-cheated Black Sheep (alien+zombie+vampire+werewolf+etc.) father.
- Self-imposed bonuses for themed fathers (all skin tones, all eye colors, service NPCs, etc.)


Points:
Each toddler skill +5
Each 'Grown Up Well' memory +5
Each A+ +5

Each Fire -5
Each D -5
Each 'Grown up Badly' Memory -5
Permitted Hacks:
- Trips & Quads hacks
- Same-sex pregnancy hacks (?)
Other than them NO HACKS!

CC:
- You can have CC aslong as it is non mood boosting or changing game behaviour to give advantage.

Win or Lose:
- You win if you succsesfully have thirty-four children without no rule breaking. [Yes, you can still win with a husband].
- You lose if:
- You rule break AT ANY POINT DURING THE CHALLENGE.
-Somebody who is related/ helped you during this challenge dies at any point DURING THE CHALLENGE.[Including the husband]

Please tell me if anything can be added, and please keep in mind that this has not been playtested-[im still playtesting]

Enjoy!

[BIG thanks to Proxian_Girl]

Is aging on/off allowed? One can simply turn off the aging in the game to prolong the life of a Sim and thus have more time for more babies. Just sayin'.

I will say yes until you have enough for the elixir of life. The MUST take it off.

I think I am actually going to try this, while combining it with other challenges. I'm going to do this to prep for the Haunted House challenge, yes I am going to kill all the childern when they reach adulthood(except my favorites of course), and to kill the kids I'm going to do my own verison of serial killer challenge. So I am going modify the rules a bit for me, but this sounds like a very hard and chaotic but fun challenge. Honestly, I am looking forward to thinking up 34 names that start with the same letter! If I remember to, I'll post pics.

Thats great! Its fine you mix it up, after all, challenges are meant for fun. I think theese sites might help:

http://www.girlsnames.co.uk/

And for the boys:

http://www.boysnames.co.uk/

Lol, how did you come up with the number "34"?

Dunno.... It just came to me XD

So if you get married, does that mean you can only have one kid with your husband and then have to cheat on him with 20 more guys? lol
Also, first it says you can remarry if the husband dies, then it says you lose if the husband dies...

Sorry about that, I changed it so it now makes sense. Thanks for telling me.

I just played this. I wasn't going based off of these rules though i was just trying to have 26 kids. right now the mom (Red) is pregnant with baby Z and I am so excited for this to be over. It's so hard. It did end up being pretty interesting though. Baby A was born from a hookup Red had way back in the beginning because she was desperate for a baby but couldn't find a good enough man. She eventually married Jim, a slacker who barely did anything and fathered B through G. They got a divorce after little Georgia was born.

Red went on to marry Blair who had a great high-paying job and was much more caring and involved with his kids. He fathered H through V. This included three sets of twins, Karev and Luther, Mink and Nell, and Reid and Sam. Having those two sets in a row was incredibly stressful. Blair died in a kitchen fire. Red went to the matchmaker and paid the maximum amount of money only to be set up with a blue-skinned alien. I didn't want the date to be a total waste so I let her have his baby anyways and now my poor Walt is half alien. Red finally found a boyfriend who gave her Xenith, Yvonne, and Z, although he never moved in of married her.

Both Blair and Jim were redheaded (Red is a blonde) and as a result a staggering eighteen of twenty-six kids have red hair. They all look the same and I am getting sick of red hair. Seven of the other eight are blonde, which is also starting to bore me.

Tips: Dont put a lot of space between kids. You're going to regret it later when a teen moves out and you can't get rid of the next one for 12 days because you took a break. It gets boring.

-Teach the kids how to study as early as possible. I taught every kid to study except Sam and whenever they did their homework he would get like 12% done and then quit, while everyone else finished in the same amount of time. He completely failed high school.

-Make the kids friends with each other so they can play redhands. and have teens befriend the babies so they can teach them toddler skills later. This is also helpful because if your kids can get social interaction from each other they will be able to send home those brats that come home from school with them (who like to harass my babies, eat my food, and stand in narrow hallways and block access to half the house. )

-Make several bathrooms and make them roomy. My house has two bathrooms but everyone always uses the small one. And they always manage to have birthdays on there which as you can imagine causes the biggest roadblock....

This Challenge sounds awesome!

I know this is meant for sims 2 but I'm going to try this in 3.