For full disclosure, I was married at 19 years old. Going on our 28th year come October. It sounds as if you, and the lady friend, are going about things the right way. Based upon the way they talk, er, uh, boast, some of the single men I work with are just out to conquer a quick one. If that was the case you would have to be quite a professional at not revealing your concealment. Outside of a derringer or lower body holster you would run the possibility of it being discovered with a casual hug. Congrats!
Let us know how things turn out. I have 3 kids finishing up higher education and they intend to qualify afterward. (So much easier when they have lived on and off campus and working on healthcare degrees due to the vast majority of clinical sites being posted.) I am sure they will have similar experiences.