Texts can be ambiguous. He could be simply attempting to stay lighthearted in a tough time, but it sounds like he was being flirtatious.
So I think you should say something. Clear the air. That sounds to me like he is crossing some boundaries that he shouldn't as your therapist, and a professional in general. Tell him clearly that you're not comfortable with him flirting with you and that it isn't very professional of him. If he does it again, I would start looking for a new therapist.
For a person with the amount of power over your emotions that they have, therapists that openly flirt with their patients are taking advantage of the often emotionally compromised people who trust them.
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