Bravo! You and a friend have agreed to take a trip together! Now what?

First, decide where you’d like to go and what you’d like to see once you get there. If you have diverging tastes as to what you’d like to do, be ready to compromise at least a bit so that you both get what you want. Also, there’s no reason why you can’t go for the double occupancy hotel room and then go your own way during the day, hooking back up in the afternoon or evening for drinks before a nice dinner out. We’ve seen men and women room mates that do their own thing during the day and have dinner with a group in the evenings, it doesn’t have to be a romantic endeavor, just a common interest.

Pick some things that you both want to do and then make time apart to do what you’d like to do on your own. That way you give each other space to develop new experiences and compare notes later.

Do, however, set some ground rules so that you can be safe. For instance, if your friend wants to go out to a bar at night and you don’t drink, be clear and upfront about it. Don’t create potential issues because you didn’t discuss it in advance. Maybe the answer is that they get an uber and get back at about the same time you are turning off the light after reading a book. There are ways to make it work if you are flexible and determined.