50K? I would go for 911 or just add more blings into the boxster to make it more fun! PS9, expensive wheels, stereo?, 3.4 engine conversion?, supercharger etc. I wouldn' go for cayman since there's zeintop and you can have the best of both worlds with the boxs...
If you love American cars, then corvette ZR is the way to go! You can always stuff your friends on the trunk and let the lady take the seat
