The goal of the OW training should always be to allow you to do just that. I see absolutely nothing wrong with it. Better to do short, shallow, shore dives (say that 3 times real fast) with someone you know. I'd advise doing that before trusting a guide or DM you don't know, that doesn't know you, and frankly is not responsible for you any way.
If you don't feeel comfortable at any time you simply end the dive. However before you finish your training sit down with your buddy and ask each other if you both feel your training has prepared you for what you want to do. If not go to the instructor and tell them you need whatever will allow you to do it. Unfortunately you may not know. Luckily you have many resources that can help with that. You should have some training in how to help each other if a problem happens and this should be in your OW training. You should have no problem perparing a dive plan with turn pressures, times, and basic navigation - again all should be in a good OW class.
When you sit down with your buddy to discuss this you are actually starting to plan those dives you will do on your trip. This is when planning begins, not at the site, not on the way there, but now - when you actually make the decision to dive.