Sometimes I think I've seen it all, and then along comes a Portal dating sim with Aperture Dating Simulator.
Created by Ashleyanna Rivers, this fully-voiced dating sim is set in Valve's popular Portal universe, but not the same one you know and love. And clearly Valve approve of it, since they're letting it release on Steam. The dev says it's not "your average fan-made Portal game" in an alternate universe that will show you a new Aperture.
You take control of a manufacturing employee thrust out of their element and into maintenance, where you'll meet 8 brand-new personality cores, each with their own special little quirks. There's 18 possible endings to find and over 30 cut-scenes with "a lot this little dating sim parody has to offer" (or so they hope).
Check out the trailer:

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