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Hi Keiran,
The relationship sounds very “new” if you are keeping him on his toes by spontaneously saying you were “staying out” (instead of going to the boring bus stop) when you bumped into him.
Are you two exclusive? You could ask him that and say that you’re just making sure as guys still approach you when he’s not around and you’re not sure what to say. You can bet that will keep him on his toes and he will contact you more!
In short, yes, you are insecure. And yes, he should be checking in with you more.
Don’t let him take you for granted! But also be honest with yourself. Is this really the guy for you, whether you had confidence or not?
Best,
Inky