maybe some youth here are wiser than me in these types of things...
Most Helpful Girls
Communication is essentiat in any relationship, from platonic friends to husband and wife. Most relationship problems start with a lack of communication.
If you miss a guy, keep it straight and simple. "I miss you" is all it takes! Simple and says exactly what you mean. If the situation requires it, you can qualify this statement by adding a reason, your hopes for the future, or whatever applies. No one can criticise you for being straight and honest.
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When I miss him I send him a message like:
Heeey! Don't make me miss you too much. Get your stuffs sorted soon. You owe me a catch up! ;)
I just send it once and without an expectation that he'll reply. I don't send another message when he doesn't reply. At least you have told him that you miss him and it's up to him if he'll catch up or not. Just don't expect and be genuinely happy for whatever he is up to at the moment. Guys get to miss girls who are independently happy haha.