Weigh costs of ending marriage before acting

I’m an established businesswoman who runs my family’s company. I’ve been married for 31 years. One of my four children works with me. My marriage has deteriorated. For the last few years, I’ve been having an affair with Herb. Although he has far less money than I do, I believe he’s not dating me with the hope of getting any of my money. What should be my next move?

First, never go with Herb to any restaurant, hotel or anywhere else you’ve gone to with your husband. You never know who will see you there. That person may call someone who knows your husband. At that point, the game could be over. Second, you need to have a serious conversation with Herb. Ask him if he wants to marry you. If yes, then ask what, if anything, he expects in terms of getting any part of the money you have, where the two of you would live, what he’d contribute to the living expenses and what he has for assets. That’s when I believe you’ll be shocked to hear Herb say that because he earns less than you, you should pay for all the living expenses. I’d bet Herb also will believe it fair, should you die before he does, that you let him continue to live in the house you two would have been living in and that you also give him one-third or one-half of your estate. In that way, he’d be able to continue the lifestyle to which you accustomed him. So if you are not willing to pay that price, then it would be time to put Herb in your rear-view mirror. Third, if you divorce your husband, under Massachusetts’ equitable division of assets, the value of your business would be — unless you had a premarital agreement that protected that asset — added to the marital pot. If so, after you add up his and your assets, you might need to pay your husband one-half the difference. So, if you have to pay your husband that much money, will you still have enough money to keep running the business? And, when you think about paying your husband all that money, is that really worth it so you can spend the rest of your days with Herb? And have you considered Herb could bail sooner than you think? To paraphrase Shakespeare’s “All’s Well That Ends Well”: “The web of (your) life is of a mingled (story), good and ill together.” I’d bet, when you add up all the good and bad times, the good times you’ve had with your husband outweigh the bad. Life is what it is, not what it was. So think hard about what you need to do to make your life with your husband something you want to stay in. Otherwise, prepare for a tsunami.