I was divorced after 15 years, and remarried before age 60 to the very same person, then divorced again, all before the age of 60. I am receiving a reduced SS payment now at age 64. If he passes away, at 66 can I still apply for divorced widower benefits or is that remarriage to the same person before age 60 a technicality that would bar me from receiving those benefits?
Yes, you can. Since your first marriage lasted for more than 10 years, the remarriage wouldn't affect your potential entitlement regardless of who you married, since the remarriage has since terminated.