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This is borrowed heavily from Zombie's Extended Congrats which I'm really enjoying. It will use a 6-sided die, I personally use this online dice simulator: https://www.random.org/dice/

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Round 1: http://www.behindthename.com/bb/game/4746344
Round 2: http://www.behindthename.com/bb/game/4747256
Round 3: http://www.behindthename.com/bb/game/4748534
Round 4: http://www.behindthename.com/bb/game/4749771
Round 5: http://www.behindthename.com/bb/game/4750820

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This round, 5 years have passed. Roll for each couple:

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1- One partner has passed away.
2- Separated or divorced.
3- No change to relationship.
4-6- Dating couples are now engaged, engaged couples are now married, married couples are still together.

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Roll for each single person over the age of 18, including any who have just become single in the last roll:

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1- Single.
2- Dating someone around their age.
3- Dating someone either much older or younger than themselves.
4- Engaged.
5- Married to someone with a child or children from a previous relationship.
6- Married to someone who didn't bring children into the relationship.

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Roll to find out how many children each married couple have this round, including your original couple (children can be born to a woman 45 years old or younger):

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1- 1 child
2- 2 children
3- 3 children
4- 4 children
5- 5 children
6- 0 children

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Singles, twins, triplets are up to you. For example, if you rolled 4, you could have 4 single births, 2 sets of twins, 1 set of twins and 2 single births, a set of triplets and a single birth or quads. You get the idea.

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Roll for genders: odd number= boy; even number= girl.

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Roll for namebanks, including names of new partners:

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1- First and middles names:
Arden Avery Bale Beckham Brando Bronson Burke Burton Chaplin Cooper Crosby Cruz Curtis Damon Dean Douglas Dylan Electra Ellington Flynn Foster Gable Gardner Garland Grant Griffith Hardy Harlow Hemingway Hendrix Holden Hope Hopper Hudson Jeter Jolie Jordan Keaton Kingsley Kitt Lane Legend Lennon Lennox Lewis Madden Manning Marsden Monroe Montgomery Murphy Palin Pfeiffer Presley Quinn Reed Reese Ross Russell Ryder Sinclair Stewart Temple Theron Turner Tyson Urban Wayne West Wilder Winslet

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2- First and middle names:
Aaliyah Adele Amelia Angelina Anniston Arlo Ashton Audrey Audrina Ava Blake Bristol Callista Cameron Charlize Dylan Elle Elvis Eva Evangeline Giada Grace Harrison Harry Hendrix Iker Isla Jenson Jude Kate Keira Kellan Kimora Leighton Lennon Liam Liv Logan Mila Miles Miley Niall Orlando Penn Pippa Presley Reese Rihanna Rufus Scarlett Serena Sienna Tatum Winslet

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3- First and middle names:
Andromeda Ariel Aries Atlas Atria Bellatrix Callisto Calypso Cassiopeia Celestia Comet Cressida Galatea Io Jupiter Leo Libra Luna Mars Mercury Nova Orion Selena Sirius Sky Starr Vega Venus

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Alexander Anne Charles Daniel David Edward Elizabeth Emma George Helen Henry Isabel James Jane John Joseph Julia Katherine Laura Margaret Maria Mary Michael Robert Sarah Sophia Thomas William

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4 or 5- First and middle names:
Adam Alexander Andrew Anthony Arthur Benjamin Charles Christopher Daniel David Edward Francis Frank Frederick George Harry Henry Hugh Jack Jacob James John Jonathan Joseph Julian Leo Louis Luke Mark Martin Matthew Michael Nathan Nathaniel Nicholas Patrick Paul Peter Philip Raymond Richard Robert Samuel Simon Stephen Theodore Thomas Timothy Victor Vincent Walter William Zachary

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Alice Anna Anne Beatrice Caroline Charlotte Claire Diana Edith Eleanor Eliza Elizabeth Emily Emma Eve Faith Florence Frances Grace Helen Irene Jane Jean Jill Judith Julia Kate Katherine Laura Louisa Lucy Madeline Margaret Maria Marian Martha Mary Olivia Pamela Patricia Rachel Rebecca Rose Ruth Sally Sarah Sophia Susannah Victoria Virginia

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6- First and middles names:
Abilene Adriano Alec Alexandrine Amalia Anja Annika Anton Arno Ashling Beatrix Benedict Benno Carlotta Carolina Caterina Cecile Ceil Christiana Christo Clarinda Clarissa Clelia Coralie Davis Devorah Dorrit Dougal Edmond Elisabeth Emilia Emmeline Esmond Fancy Federica Helene Hendrix Isabeau Isobel Izabella Jennica Jessamine Jolie Josiah Kalman Laurence Linden Livia Lucia Maddalena Marco Marguerite Mariel Marta Maxim Micah Morgana Natalya Niall Nico Nicola Noam Paolo Perla Phyllida Rosa Sampson Sarai Sarita Simeon Stefano Sylvie Tereza Tessa Vittorio Willa Willem Willoughby Yulia Zadie Zandra Zara Zuzanna

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Surnames (your choice): See namebank 1.