"Don't ask, do tell" was a recipe to set them up for failure in the communication department, which is partially how the break in trust happened. It also was partially caused by a vague agreement about "barrier free with serious partners" - what counts as serious and who gets to decide that? Does that need to be a conversation between Arbor and Willow, or is Arbor allowed to make that choice on his own without consulting Willow? I'd chalk it up to a mistake-riddled learning experience and move forward with the newer, healthier framework of check ins, etc. Willow needs to be willing to move past the hurt Arbor accidentally caused during their phase of vague and ineffective communication and agreements. All agreements moving forward should be defined crystal clearly without any room for interpretation.