Rebshidduch: 1. Is this a regular thing?
2. Does he talk to you at all?
3. Where is holding Yiddishkeit-wise? Especially in terms of Tznius-issues?
4. Where are you and your friend holding?
5. Are you or your friend uncomfortable with the situation?
6. Does he have another option?
You don’t have to answer the questions to me – those are just the questions that you might want to address for yourself. If the situation bothers you, I think you should ask a Rav. Personally, I think it’s something that needs to be asked to Rav. I certainly don’t feel like I can answer it. (other than saying that if you are going to give him a ride, I think you should drive and he should sit in the back, imho. I think giving him the car keys sounds too friendly).