It was stated that the victim's DB9 was damaged by a suspect. The picture shown on the cell phone is actually that of a DB7.
When El Oso's men grab Castle, they put a chloroform rag over his face and Castle instantly passes out. Chloroform actually takes a few minutes to take effect.
Considering she managed to come up with, plan out, and execute - all completely under the radar - an extravagant 'murder mystery' for Castle to solve in "The Lives of Others (2013)", it's unlikely that, even off the cuff, Beckett would be unable to plan something as simple as a date night.