I like this topic, so I'll update with some new happenings:

-Heather Huffington has had two kids, a girl, Summer, with Castor Nova, and a son, Bobby, with Ashley Pitts; both out of wedlock.  Both are surprisingly good-looking kids.  She's currently pregnant to her third with Dustin Broke, who is married to Angela Broke.  I don't have high hopes for this child, as Dustin is prone to having hideous children.  Heather's daughter went to Sim State and just pledged the sorority and Bobby just grew up into a teen.  He's got his eye on Samantha Indie, the daughter of Mitch and Tiffany Sampson. 

-Castor is currently engaged to a townie (after he had Summer with Heather).  He is in the Intelligence career path.

-Lilith has had four kids (Alex, Jacob, Karina, and Grace) with a CAS and is currently pregnant with twins.  She was caught cheating with Castor Nova at Bobby Huffington's birthday party when Castor Nova made out with her in front of her husband and her daughter.  Not too smooth.  She made it to the top of her career as a Visionary Artist.

-Darren Dreamer married Brandi Broke and she is currently pregnant with their first child.  Dirk is still in college.  I'll probably set him up with Tessa Ramirez, who is currently going to college too.

-Kevin Beare is still in college.  He's engaged to Stella Terrano, the alien YA.
   

Great topic.  Its fun to see how everyone plays.  I stick to Pleasantview.  So here it goes:

The Pleasants (This is the family I play the most)
-Daniel was caught with Kaylynn after Mary Sue came home after being fired and quickly moved out.  He moved into a small house Downtown where he has romanced many passersby, even into his elder years.  The closest thing to a real relationship is the VERY open relationship he has with Heather Huffington

-Mary Sue divorced Daniel on day one and currently hasn't taken up with a new beau, let alone remarried.  I moved the Oldies in with her, but really only to get them out of the bin.

-Angela has only been with one man: Dustin Broke (despite his beady eyes).  She got pregnant with twin girls, Charlotte (in college, currently living with Max Flexor) and Emily (who had twins with Orlando Centowski), during her second semester at college the first time either had woohooed.  They later added a third girl, Virginia, and she is currently pregnant with their fourth.

-Lilith spent most of her college years woohooing as a member of the Tri-Var Sorority.  So much so that she achieved her lifetime want of woohooing 20 before she graduated.  In her senior year, she changed her ways and entered a committed relationship with a Created Sim, whom she later married, has had four children with (Two Boys: Alex and Jacob, and Two Girls: Karina and Grace) and never once cheated (neither has her husband).  Her husband has reached the top job in the Entertainment Career and she is near the top (maybe #9) in the Artist Career.

The Goths
-Mortimer quickly married Dina (no ceremony) and got her pregnant their first night as a married couple.

-Cassandra married Don and is currently carrying his child.

-Alexander is still a child.  I'm thinking of maybe pairing him up with Lilith Pleasant's daughter Karina, when they're of age of course.

The Calientes
-Nina has her eye on Malcolm Landgraab's fortune.

-Dina married Mortimer for his money, but is secretly having an affair with Don Lothario.  It's not too hard, seeing as how they both live with the Goths.

The Brokes
-Dustin is the only one I have played extensively.  I sent him to college and had to assemble a shotgun wedding when he got Angela pregnant on the first shot.  He's a CEO, and has had two affairs: once with Roxie Sharpe, just once, at Lilith's wedding, and with Heather Huffington, of whom he has kept up the affair without Angela knowing. 

-Brandi had the baby.  Don't remember the name and hasn't progressed past infant. 

The Dreamers
-The Unlucky in Love Dreamers... sigh.  Cassandra Goth spurned all of Darren's advances and went on to marry the womanizing Don.  Dirk went to college but lost touch with his high school love Lilith after she installed a revolving door to her bedroom.  He's still currently in college.  Haven't decided which way I'm going to send him.

UNI

Heather Huffington has made Lilith Pleasant look like a nun, nearly doubling her "score".  She currently runs a home business where she... "entertains" male guests.

Tiffany Sampson had a relationship with Castor Nova, but they were headed in different directions.  She met Mitch Indie and the both fell head over heels.  They got married shortly after they graduated.

Brittany Upsnott graduated and is living with Joshua Ruben.

Roxie Sharpe joined the Tri-Var Sorority and is still there, mostly in order to keep the house open.