Well, serial romantic did make sense... I needed enough points to get the 'Connections' reward to give him a kick start with his career. As well as nooboos in every filled house so that I can stave off empty world syndrome like my first dynasty suffered from. I also wanted him to max out charisma which he's done thanks to buying the "Great Kisser" reward. I'll use a helper to errr... make extra nooboos with townies as needed but it seemed crazy to 'give' those points away when Winston needed them.
I'm glad it wasn't too shocking a start to the dynasty. I did toy around with the idea of doing this all 'behind the scenes' as it were and just start the story from when he begins to move in helpers but at the end of the day I like the story to be true to my game play.
So yes, to answer you Nettlejuice Zoe, is pregnant to Dude, as are most of the other sims he kissed. His family tree is pretty dynamic! So... I wonder how I'm going to get him to settle down? Hmmm... maybe Weston can help with that. Oh, and isn't it just my luck to get a sim who's name is nearly the same as Winstons?