FWIW, I'll try to explain my reading: I didn't read "I have a long history of close relationships" as a riposte to "Sounds like you have a problem with planning making friends", because it didn't seem to me like a direct contradiction. One can have relatively long close relationships without planning to have them. In fact in that context it kind of sounded to me more like "Well I have real friends, not planned ones".

So then I read "talking to someone for 45mins isn't a big deal" as reasoning for the objection to planning (i.e. "don't plan, just talk to people") rather than a contradiction ("45mins isn't long enough to form a friendship").