Some people don't, at least not the brutally honest kind, so wording it that way might help.
[Which makes him feel like maybe he should bring up that thing he did that one time that made him super uncomfortable.] Speaking of, you remember when we were on that beach, hell if I can remember what that island was called...the one with the boats?
no subject
[Which makes him feel like maybe he should bring up that thing he did that one time that made him super uncomfortable.] Speaking of, you remember when we were on that beach, hell if I can remember what that island was called...the one with the boats?