I think my love of choose-your-own-adventure games is well documented, but I am so absolutely hooked on When In Rome….. right now. You play a poor orphan who comes to imperial Rome to make their fortune, in the reign of…..the Emperor’s never specified but it’s quite clearly Domitian, and that fortune can be made in all kinds of ways, from working with a slave dealer or as a scribe to a (female!) scholar, to becoming a courtesan or a poet. And being set in the reign of Domitian, there’s quite a lot of political discontent and conspiracy for you to get caught up in…..
Obviously I went straight for the poet path, and it is perfect; you fall in with a poet called Valerianus, who’s heavily based on Martial, plus his boyfriend Hedylus and other poetical friends, and join in their bohemian life of freeloading, reciting at orgies, making up terrible epigrams about the rich and all the while trying to create some genuine art.
But the other paths are equally as great (I particularly like the one where you become the tutor to your patron’s young son/daughter; firstly because they have a mad crush on you which involves lots of pointed and longing quotes from Catullus, and secondly because they’re kind of an adorkable idiot) — the details of the setting and attitudes are just right, and the narration/dialogue gets across the characters so well.
Also, while relationships aren’t the main focus, the Romans were pretty upfront about this stuff, and so there are plenty of opportunities of all genders. :D
It’s still in alpha testing at the moment, but a large amount of it is already complete, so do give it a try and leave some feedback! (and then come and squee with me about the loveliness of Florus — ooh, and Marcus Attilius too…..)