This is probably less complicated than it seems. The very best thing you probably can do is to look at the pension documents and the hospital insurance policy you have to see what benefits you would retain if you remarried. In answering this, I am assuming that you are receiving benefits from your deceased husband's previous company/employer. Very often, there are help lines for people in your position that are set up by the employer to answer questions. Call anonymously if you feel uncomfortable, and have a list of questions written in front of you so that you can take notes. Also, if you are in danger of losing these benefits, don't forget about some others to which you might be entitled, like Medicare (all parts) if you are over age 65, Social Security, Veteran's benefits if they apply to you, or other "extra help" benefits for lower income people. If any of those apply to you or your new spouse, you may be able to replace some or all of the benefits you lose through marriage. One last thing: It is probably a good idea to make sure you have a will that reflects your desires, particularly if you live in a community property state. Marriage could alter some of your asset distribution, and wills are fairly simple most of the time to update or re-create to address a change in circumstances.