Wow...2 whole months.
This is a personality trait you know? Some people are planners, some are spontaneous. You found one where organization is optional - spontaneity reigns supreme.
Check out his closet - are the shoes all lined up neat and in a row? Or does it look like a cyclone hit it? There's your answer.
More about this in MBTI - you can google it.
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Maybe he seems to understand the phrase "burning the candle at both ends"... more than you. you dont HAVE to see each other every weekend.
Maybe he's just used to that you always set up schedules and thinks that you better arrange time? You can wait ofc to figure out, but he may think that you're busy as well if you don't tell him to meet, so...
I think you've already surmised that he is seeing someone else.
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Bring it up to him. Don’t wait - that’s childish.
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