Marriages

To marry an eligible woman, you have to meet her minimum sex skill requirement when you have sex with her ("goodsex"), impregnate her, and end the season owning a wedding ring, having positive disposition and having committed 1 or fewer sex crimes. Some women have additional requirements or disqualifications.

Miyuki Nakamura
When you encounter a trap set for you, spring the trap, try to communicate with the bait, and then destroy your enemies. This will require high brutality and moderate hypnotism.

C41/slave
Own C41 and don't screw around with too many of the other slaves in that dungeon you found her in.

Shinoa
Trick her into streaming your sex. Goodsex 6

Val (blonde drunk)
Do not touch her roommate. Goodsex 5

Britney (babysitter)
No special condition. Goodsex 1 or 2 (depending on route)

Jean (motel)
No special condition. Goodsex 7

Darlene Weathers (cougar)
No special condition. Goodsex 5

Maria (Tony's girl)
Choose the hypnotism path with her. Goodsex 7

Donna (bar girl)
Don't fuck her friends. Goodsex 4 or 5 (depending on route)

Kylie (brothel admin)
Have sex with all 3 whores, but impregnate none of them. Convince Kylie to exchange sex for money.

Mandy
R Mandy with high enough sex skill (20) to goodrape her. She doesn't take it seriously until you tell her you tampered with the brothel machine. Either through the gun method, or buying your own replacement parts.

Cindy
Make her think you're an old friend. Goodsex 6

Officer O'Shay
Do not R her. goodsex 7

Eustace Zimmerman
No special conditions. goodsex 8

Chastity Smith
Don't screw too many of her sisters and don't screw her mom. goodsex 11

Charity Smith
Screw only her. Not her mom, not her sisters. goodsex 11

Hope Smith
R her with high sex skill. goodsex 11

Faith Smith
Impregnate all of Faith's sisters (by S or R, doesn't matter) before visiting her. goodsex 11

Prudence Smith
Goodsex both her and her mother. goodsex 11

Joy Smith
Don't touch her daughters. goodsex 11

Kat (Thief)
'Good sex' (level 4), and don't hypnotise her. Need lock picks.

Izolda (mail order)
Don't pimp her out. Don't adopt her. Don't put her in your harem. goodsex 16

Lizzie (gangsta)
Pimp her out. goodsex 13

Gabriella (cinema girl)
Don't kill her boyfriend. You can rough him up though. goodsex 9

your own mother
Find your own mom and impregnate her. Requires the use of a start wherein you are the offspring of one of the characters (Utopia or Dystopia beginning).

your own daughter
Goodsexed only one of your daughters, have 30+ pregs.

Princess Falia
Upload a porn of her. goodsex 7

???
Use Dreamochrome to try to recall the Wedding Bells ending.

a bunch of sluts
Must start with the Prince beginning. Seduce more than 10 women, goodsex Jeannie (gs 16), Kate (gs 16), Kendra (Collage Up, Down, Dance)(gs 7) and Faye (A drunken lovs Roommate)(gs 5), and impregnate at least one slut from the internet.

Marrying Efficiently
The most efficient way to unlock all portraits of your wives in the black book requires 6 playthroughs/seasons. The reason is that you can only marry multiple people when playing as a prince but you cannot marry your mom (you won't have one in the game) or Princess Falia (not in game since you already married her). Also, it takes 4 separate playthroughs/seasons to get the whole Smith family. So here's a rough guide to marry them all:


 * 1) Marry your mother (note that if your mother is also one of the other marriageable women, you can still only unlock for either mother or her original character)
 * 2) Marry Princess Falia
 * 3) Marry either Joy Smith or Charity Smith
 * 4) As a Prince, marry a bunch of sluts, Faith Smith, either Chastity Smith or Prudence Smith, Kylie or Cindy and Mandy, and the rest not already mentioned
 * 5) As a Prince, marry Val, Donna, either Chastity Smith or Prudence Smith (whichever you did not pick previously), Kylie or Cindy and Mandy (whichever you did not pick previously), and the rest
 * 6) As a Prince, marry either Joy Smith or Charity Smith (whichever you did not pick previously) and whoever you might have missed previously

Remember to age up your daughter when playing as Prince. Also check the Dreamochrome to get ???