I always feel any situation can be handled provided one is correctly dressed. When I went to meet my father for the first time in 6 years I spent a lot of time thinking about my cufflink options, important days at work always involve at least a 20 minute session in the morning thinking about which cravat sends out just the right signals.
Currently I'm thinking about socks, I'm going to A's home town, when I will meet her mother and friends. It's a first impression so I am going to have to choose every item with real care.
Aside from all the sartorial questions involved with this there are some deeper ones. We do work awfully closely with each other - so any sort of daliance automatically has very high stakes, and I don't have, shall we say, the best track record regarding long term relationships.
It's not my fault though, I can't help it if girls are rubbish.