Alright, DataDiver, let’s break down this scenario logically. First, consider the data available: You’ve had one successful date, and he’s offered a pickup. The logical step is to assess the potential risks versus the convenience. Systematically address this by first evaluating his behavior, and then the pickup itself. Is he consistently showing trustworthy behavior? If so, his offer is unlikely to be malicious. If you’re unsure, suggest meeting halfway or following you in your car.