Everyone is different. What comes naturally to some doesn't come naturally to others.
For a lot of people (me included) keeping in touch with others doesn't come "naturally". We miss contact, and yet we sheldom establish it. There are many reasons for this: poor time management skills, low self-esteem, simple lack of practice, etc. In any case, it takes effort to break out of it.
Try to think about something that others do, and that you would like to do, but is difficult for you. Exercise, learn a new language, go to bed earlier, eat more healthily... whatever. This might give you a perspective of what it is like to have this "friction".
I see what this person is doing as a way to remove the friction and create a new habit. I have no doubt that when "they gets the thing rolling" with someone it will gradually easy to keep engaged without the machine "dictating" anything.