Ans: Obviously not. Whether you are going on a road trip or on a week-long trip out of the country, it could be risky.  A single meeting doesn't tell much about a person. You've to ensure that you both are comfortable with each other. You have to stay in a hotel room 24/7, there is no privacy, you have to dress in front of him, do makeup which is really a funny thing when you do in front of someone.  You might be don't like some of his habits, and many other things could make your trip ruined.