How to handle this situation with Cappy?

Yes, this is my predicament. When he invites me out it's normally a dinner and drinks. It might have to be done on text yet...but that won't go down well either...or except a date and just blurt it out. If we hang in a group next time...that's not the best time either but I'm going to do it. Perhaps, I'll suggest something along the lines of if he meets someone or she's hot you should go talk to her..