I would probably date Nautica from Transformers: More Than Meets the Eye, were she an actual existing person. She’s an adorable, well read, left leaning, politically minded, sweet purple lady that likes cats. Basically my girlfriend, if she was a giant robot that turned into a submersible vehicle and had engineering knowledge.
Obviously the first step to dating a giant robot lady is transferring your mind into an appropriately scaled gynoid body—if that technology were available presumably the opposite would be as well, but why would you do that.
After that, sharing favorite fiction would be a must, and then critiquing the flawed parts and discussing how we’d change it. I’d also love to hear about writing from Caminus and Cybertron. Discussing the state of present day politics over drinks would also be fascinating—we’d be similar enough to agree on a lot, but different enough to have spirited debates.