Men, When does it become pathetic or desperate when contacting someone you just started to date?

So I’ve been dating an old friend. He reached out randomly. I reach out randomly. But I think I’m more honest and forward. So I’ll tell him that he crossed my mind and I’ll ask about his day.
Recently, I had nothing to really say but I literally just wanted to be in contact. I wanted to reach out and basically just say “have a good day” but a friend (woman) says it looks very desperate and to delete his number. And she told me not to reach out until he does. So for all the men, is there anything that turns you off about a woman when dating? Like, is there something that would make you think she’s desperate by how she texts or calls?

Men, When does it become pathetic or desperate when contacting someone you just started to date?
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