Thing with catching up with old friends/acquaintances is that you sometimes don’t know if you still connect with them. It might be a while since you last met, and having moved on in different directions, there is a very good chance that you don’t connect with each other at all. Yes, there is the environment you shared several years back that connects you, but when that becomes the only source of connection, it can get rather boring and you might be itching for the conversation to be over.
In order to determine whether you still connect with an old friend/acquaintance, I have a simple test. I must warn you that this test has no predictive power – it won’t tell you before you meet your friend if you connect with him/her or not. It, however, analyzes post the event how well you connected. And can help you make a decision if you have an opportunity to meet them again.
Invariably, I’ve found that when you catch up with old friends, sooner or later, one of you will ask the other, “so who else are you in touch with?”. Between any two people, there are always these “filler lines”, what you say when you realize you have nothing to talk about. With old friends/acquaintances, it is this. Remember that your only connection is the environment you shared a while back, and the other people that inhabited that environment. So, in the absence of anything else to talk about, you end up talking about this.
The metric (I know I’ve been meandering) is this: from the time you meet your old friend/acquaintance, measure how much time it takes before the conversation goes to “so who else are you in touch with”. This gives you an indication of how well you connect with this person. The longer the time gap between you people meeting and this question coming up, the better you connect – it simply means you have so many other things to talk about, so this doesn’t come up.
This afternoon I met  a friend from school and in the hour and quarter we spoke, this question never came up. This indicates that I still connect with him pretty well. At the other extreme there have been people with whom the question has been popped within five minutes of meeting – showing how far we’ve drifted and there’s absolutely nothing to connect us any more.
There are times I’ve been surprised, either way. Once I met a senior from school not knowing if I had much to talk to him. The question was popped only forty five minutes into the conversation. We’ve subsequently met a couple of times. Other people I’ve gone to meet thinking of a dozen things to talk to only for them to start the conversation with “who have you been in touch with?”
I’d once visited Bishop Cotton’s Boys’ School in Bangalore (for a chess tournament) and noticed this board somewhere in the school. It said (paraphrasing):
Great minds discuss ideas,
Middling minds discuss events,
Small minds discuss people.
On similar lines, the filter for relationships has been, “What else?”. If either party has had an opportunity to say this in the early stages, it has raised questions about why conversation has run dry.