The first car is a no brainer for me: Aston Martin Rapide.
So that's one down, what about the second car? Well I have something somewhat reasonable for day-to-day driving, so I thought about something really fun and a little outrageous. A sporty roadster comes to mind. Unfortunately I had a problem choosing a roadster that I actually liked. Originally I thought about an SLK, but that seemed too boring. Then there's the Aston Martin Vantage Roadster and the Jaguar XKR Convertable. Both seem too similar to the Rapide, and a little too tame. I wanted something more ridiculous, but not Aventator ridiculous.
Enter R8 Spyder:
I think this is better (though probably less practical) than a friend, who picked some of the ugliest cars I've seen. D= and D=. What would you choose?
I spent too much time one this, and not enough time studying for Databases. Oh well.