LW's brother is duplicitous, but if the family "go behind his back" after having tacitly agreed to his deceptions, they simply compound the duplicity.

The first step is to nail bro to the floor and tell him that at least one family member is not in agreement with his wishes. Thus, bro has a choice - he can tell his fiancee himself and gain some stand-up points, or he can pretend to, which is most likely the case, or he can refuse to. If he clearly tells his fiancee, the family's job is done. If he pretends to, or refuses to, then it is up to the family to "call his behavior", preferably in his presence, so that there is no doubt. While an overt discussion might be seen as confrontational, I suspect it is, in the long run, the most honest, the most authentic. It also allows the brother to "style' the moment, which may tell more to his fiancee than anything the family might choose to say......All it takes is "....you know, we were wondering if BobbyJoe mentioned his other prior wives....... we assume he has". And, it eliminates any doubt about who said what to whom, it eliminates a secrecy that the information hardly deserves, and it allows a forthright discussion about the marital escapades of the groom in a manner that may be either vastly reassuring or deeply disturbing, depending upon what the marriages constituted and what the constitution of the fiancee is.

There is, after all, no shame in multiple marriages, just a certain display of fecklessness, which he may/may not "be over" (I note that Frank Lloyd Wright had four wives, three of them his, and one of them the wife of a client. Ultimately, because Wright was a genius and a master salesman of his talent, we view his personal life as "eccentric", not feckless.....). Thus, speaking the truth should be a matter - of - fact deal here, not some game of cloak and dagger, midnight communique's, the phonecall out of the blue. The family need to own their honesty openly, not covertly. If this is too much for the Feckless One to handle, then it demonstrates the shallowness of the relationships that he has with his family of origin, and he can drift off to more parasitically profound ground.....while the family tend to some level of support for the new nephew/niece that will shortly emerge upon the extended family and support the wife or almost-wife as best they can, emotionally, and with continued contact.

Yep, there is certainly a connection between LW's avoidance of grief at 16 and his partial occupancy of his adult life. Emotions come attached; supressing grief and anger then creates a circumstance where all other emotions tend to be supressed as well. One doesn't get to "pick and chooose" which emotions one feels.

Given the circumstances that this man was faced with at 16, represession was probably what he was able to do; there was no support/modeling of grief/anger for him to turn to, and indeed, men are socialized in our culture to not express (and thus not feel) feelings. (Boys don't cry, keep a stiff upper lip, etc....) Emotional expression tends to be identified as a more "soft" and "feminine" trait. Unfortunately, that's a crock. And - Cary is right, the survival tools that worked at 16 are now inhibiting in his adult life. Time to go sane.

Working with a great therapist might well provide substantial recourse, and I might suggest that he seek out a a therapist skilled in working with EMDR, a tool that allows the rapid processing of intense feelings. It is not a "shortcut" or emotion-advoidance tool, but rather a powerful tool of enablement and empowerment that allows intense feelings to be experienced, absorbed and discharged. In that process, he may also attack some of the feelings of inadequacy and insecurity that seem to surface around the edges, given his choice of words. And, a skilled therapist will help him place in context the dying and death of his mother; it sounds as if his family of origin may not have been the most ideal of families to begin with (whose is?).

As he does his "work" he needs to keep his wife fully involved in the dynamics of his change..... while she may resent his half-presence as is is currently expressed, she is now quite accustomed/habituated to it, and she may need to be proactively aware as he becomes more vibrant, more aware, more engaged, that this will impact their relationship quite profoundly. If she is up for it, their marriage could reach wonderful levels of compelling intimacy.