Not technically dating
Malory liked the name Sterling and decided to name him that.
Woodhouse suggested that his middle name be "Reginald", after Captain Reginald Thistleton (a deceased friend of Woodhouse's that served in World War I, with whom Woodhouse may or may not have been infatuated), but Malory decided that Reginald sounded "too gay" and instead named him after herself.
At some point as a child, Malory moved without telling Archer's boarding school, leading to him to take a train home alone and eventually ending up in a police station.
Malory had to pick him up and continues to view the situation as not her fault, stating that he could have picked up a phonebook.
Sterling spent the first five years of his life being raised by Woodhouse and only seeing his mother a few times per year, such as on Christmas.It is unknown if the rest of the group, apart from Lana and Cyril as they were present for the confession, is aware of this.When we first see Sterling Archer, he is in the middle of a KGB torture exercise being run by Crenshaw.Archer states that she came onto him and so it was not his fault.During his freshman year, Archer was given a swirly by Richard Stratton IV and Trent Whitney in a toilet that Whitney had pissed in.
implying he is at least smart enough to receive a bachelor's degree in an unknown major (although according to his mother, he flunked out of college).