Yes. The rule against double texting exists to protect people from looking eager, which is a thing worth caring about roughly zero percent as much as most of us do. What actually reads badly isn't a second message — it's a second message about the first one.
It is not desperate. 'why aren't you answering' is desperate. A new thought is not.
If your second text could stand alone as its own message, send it. If it's a follow-up on the silence, don't.
“just saw something that reminded me of you —”
“adding to my earlier point, unprompted:”
“hey, still want to lock in a day for this week?”
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Was It Casual is for reflection, not therapy or professional advice.