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I have a very specific life-event happening tomorrow with a definitive beginning and end with a definitive outcome. Should I text or e-mail T tomorrow to let him know how it goes or would this break a boundary? I feel like he either relaxed this boundary just this once or he may be giving us more flexibility in communication. Thoughts?
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It sounds like he wants to know how it goes, so I'd tell him tomorrow.
Do you think being scared to contact him comes from your own stuff? Such as, fear of "breaking someone's boundaries" = walking on eggshells. Healthy people are often flexible with things that are not of a serious nature (such as a phone call or email).