Dear Andrea,

What I am going to say may hurt.

I presume your friend is your age or older. If he is serious about religious life he has to make a clear decision about his relationship with you. I honestly do not think he can make a mature decision about religious life if he has a foot (or his heart/mind) in both worlds, the world of total dedication to Christ through the vows and the world of more exclusive human love. If he wants to test the religious vocation he has to leave you.

I have no idea of his spiritual itinerary, if the vocation is something recent in his life or something that has been always "there" and wrestled with perhaps but never acted on. In the latter case, it is all the more urgent that he make some sort of a decision, because this never quite deciding for and never quite leaving behind the idea is not good for him. He has to go for one or the other, and if he honestly feels that he cannot now decide radically for the vocation I would tell him not to worry, he should decide radically for marriage and leave all thoughts of the vocation aside. He will not be wrong in doing this and he need have no scruples about it. As things are he is doing no good to himself, nor to you, nor to anyone else.  

I say this also out of fairness to you. He has to decide if he is going to marry you or not, and if he is not he should not hold onto you; if he is he should not hold onto anything else, he should give his whole heart and mind and life to you. 

Now, you mention your own vocational dilemma. It seems your thoughts on the vocation are vaguer than his, but the same principle would apply. If you are not relatively sure that your call is to marriage you should look into religious life, but letting go of everything else, being ready to give up everything else.

Andrea, bring these thoughts and your own feelings and reflections before Christ. Go to Mass often, receive him in Communion, examine your conscience and go to confession so as to purify your soul from attachment to anything that is not Christ, and let his voice speak to your soul. There you will find your peace and will be able to make the proper decisions.

God bless.