I've faced a similar dilemma with friends who are going through bad times in life, like a divorce. You want to be supportive but it can get repetitive and dreary to go over everything again and again, and you can start dreading the encounters. A weekly get-together seems like way too much if the writer is at this point with a friend. If you could ease back the frequency to every month or two, you might find you are less bored and there is more news to talk about. I'd also shoot for shorter visits.  Breakfast is usually served more quickly than dinner, for example. Mostly I agree with others who suggest aiming for an outing. I find going shopping together works well with a female friend because you can walk around and try stuff on, and even get a couple of errands done while chatting casually. Meeting for coffee before going to a play or a movie is also good because there's a time limit -- you chat for, say, 30 minutes and then it's time for the event to start.