As a guy who is shy about asking a girl out, here is my take. If you have been free other weekends and he didn't ask you out, it's just small talk. But if you've typically said you had plans, he was probably looking for an opening to ask you out. If you give even the hint that you may only have tentative plans - like this past weekend - he won't want to make you choose or inconvenience you or, most likely, get shot down. If you want him to ask you out, be clear that you are free. If not, just give him signals that you're not interested such as referencing another guy you're seeing or crushing on.
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I would think he wants to ask you out or something.
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He might be too insecure about asking you out
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