I have been dating this guy off and on for about four years for months at a time. We go our separate ways either because of me or him at different times. So today he told me he does certain things sometimes so that he can "Keep me on my toes", what does that mean?
It means he doesn't want you to get relaxed or comftorable in the relationship. He probably wants you to always be fighting for his attention and trying hard to impress him. In other words (no offense intended here) he is probably a douche.
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It means he wants to aggravate you. Baiscally, that's a really douschy thing to say. he wants to make you jealous, wants to keep you guessing, etc.
To keep you on your toes means he doesn't want to be predictable.
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