All of the dates we've had since we separated have been initiated by me. We had a conversation early on where he said that it was okay for me to initiate these requests so long as it was okay for him to decline them. He has declined twice, but accepted all of my other invitations. It works out that we've had a date about once a week since we separated.
On Thursday, when I called him to set up the money talk we had on Friday, I asked if we could get together over the weekend. He said that Friday night wouldn't work, but that we might be able to do something on Saturday. I said something like, "Can we go ahead and set up a time? I feel like when we make plans, they are vague, and then we have to call each other and have another conversation about the details." He said, "That's because you're asking to see me more than I'm comfortable with, so I'd like some time to think about it first." I apologized and said that he could get back to me later. He thanked me and said it was okay. When we met the next day (yesterday), he accepted my invitation for Saturday and we made plans for two additional get-togethers on Tuesday and Wednesday. I noticed that he took the initiative to make concrete plans (times, locations) for all three meetings. He even made a reference to not "stringing me along" anymore regarding our plans.
My question is -- should I continue to ask him out on dates? My concern is that these dates may end up draining his emotional tank even further if he's only doing them for my sake. On the flipside, I worry that he won't take the initiative and that I will run out of patience and end up doing something even more damaging in the long run (e.g., getting angry at him) if I feel neglected.
