Heir
Richard Bennett (1312 - 1342) & Anne (Wood) Bennett (1312 - )
Married 1328
Children
Thomas Bennett (1329 - 1348)
Joan Bennett (1331 - )
Katherine Bennett (1333 - 1335)
Ralph Bennett (1335 - 1336)
Ida Bennett (1337 - )
Denis Bennett (1339 - )
Colin Bennett (1341 - )
Story
Richard Bennett and Anne Wood were married in 1328. They lived and raised their children on the Bennett family farm. Richard tried to take over the farm work after his mother and step-father died, but could never much get over his distaste for the work. He had no interest in other work or personal passions, so stuck with begrudgingly managing the farm as minimally as possible. 
Anne, however, was passionate about painting and the family became quite prosperous due to her efforts. Anne and Richard actually met through Anne being mentored in painting by Richard's mother, Agnes.
Anne had no great interest in having a large family, but felt the pressure to have at least enough children to carry on the family legacy. She was not an uncaring mother by any means, and became closer with her children as they aged. Richard also engaged with the children in his own way, but his tendency to avoid much responsibility persisted in this area too.
This second generation of the Bennett family lived during the Hundred Years' War and miraculously (as of current writing - year 1352), none of the men were drafted. 
As the eldest son, Thomas was selected as heir; he married Leticia Taylor and had two sons, Warin and Henricus. Thomas and Leticia were completely in love. 
In 1347, Joan married Adam Beckett, a wealthy business man with whom she had nothing in common. Joan was miserably married, and developed a deep friendship with Leticia who always supported her. In 1348, the plague took the lives of Thomas and Leticia as well as their only surviving son, Henricus. Joan's husband Adam also died of the plague, leaving a heavily pregnant Joan alone. Joan's son Galfridus was born in 1348 and after a brief mourning period, Joan has been quietly raising her son with the large inheritance left by her late husband.
Ida is now of marriageable age and becoming quite the socialite. She is currently trying to decide which of her (several!) suitors to marry.
As of now, the title of heir remains uncertain until Denis reaches marriageable age. I was so upset about how many sims I had die from the plague in both my main family and side families.