Looking for pointers on first in person catch up after NC

Background:

My ex and I broke up two months ago after three and a half years together (it was the only time we broke up). We were both under a lot of stress and not communicating well or looking after ourselves. I was depressed and was acting needy, whereas he was doing the avoidant thing, which fueled my anxiety. We were both emotionally and physically exhausted and I overreacted to what I perceived as his indifference, and he felt helpless and also got hung up on the fact that he had stayed in past relationships for too long. The break up really was the best thing for me at the time as it gave me a chance to focus on myself and turn my life around. I feel really great now, but I still miss doing things with my ex and am hoping, if he has done some reflection and self-improvement, that we could build a new, amazing relationship together.

Anyway, after a month of no contact and heaps of personal growth on my part, I reestablished contact and we have been texting for a fortnight. He initiates contact sometimes and is friendly whenever I text, but it is all pretty superficial and I think he is still sad and also confused about what he feels. Today I asked if he wants to go for a drink after work, and we have arranged that for this week.

Question:

I realise that the point of this first catch up is to have a relaxed and fun time together and not bring up the breakup or the future. I expect he will be suspicious of my intentions and will have his barriers up (he will think he needs to stick with the break up decision). My question is: should I be trying to get a vague plan / agreement in place for a second catch up before we end this one? Or is that too pushy / likely to make him extra wary? From my perspective, I think I will need a couple of face to face catch ups and conversations with him before I have enough info to decide whether to keep pursuing him, or to give up my hopes of a new relationship with him. While I realise I need to take things slowly as we rebuild trust, I also don’t want to drag it out forever for my own sake.