Have to agree with 4HP, it shouldn't matter where ur route is heading. Pilots have to fly to more than one destination during their career and perform to the same high standards every time. When it comes to an IR ride it was my understanding it was always the examiners choice where he wants to go. He then gives you a chance to plan your route and off you go, very rarely will your ride go exactly as it has done in your training. Sorry dude.
As far as if it will affect your GF chances, I would say yes. When an airline hires a new pilot they WILL look at your training history. If it takes you 4 attempts to pass an IR, it is unlikely you would pass your sim ride, at least without extra training. Reality check, you think ur IR was hard...........
At the end of the day the company will see it as a liability, training costs are high and they have got to envision you as a future captain of their aircraft.
In the UK, if you fail a CPL or IR ride three times, I believe a panel at the CAA decides whether or not they will allow you to continue training, as they may decide it is not the right career for you.
Thats my view on it anyway.
Cheers
DB