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I thought if someone was blocked on your iPhone
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Unfortunately not. I think it depends on the service provider. I once had a provider that allowed me to block a caller but not their text messages. My current plan allows me to do both. By default, you can block someone but still send outgoing texts to them.
I can understand why he's "worried" about you. One, you recently lost that job, and two, he presented you with an unfavorable idea and is now concerned over your silence?
Did you respond back? I wouldn't if you're really wanting to cut him out. It's possible he's after you over his own sexual and financial gains.. and perhaps he's wanting to sexually "train" you for the "job".. pure speculation, of course.