Not creepy at all because they know each other very well! It would be only weird if they weren't close because then it's kinda like spamming. If he didn't know her very well then a one off "Good luck" in the beginning is a nice way to express interest and care towards someone you're trying to get to know imo :)
Is this considered nice or weird/clingy?
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Not creepy at all because they know each other very well! It would be only weird if they weren't close because then it's kinda like spamming. If he didn't know her very well then a one off "Good luck" in the beginning is a nice way to express interest and care towards someone you're trying to get to know imo :)