09/29/2015 02:40 pm ET Updated Dec 06, 2017

Looking For Love Again: A Widow's Guide


Senior women who have been widowed enter the maelstrom of late-in-life dating with a ton of relationship experience. Lots of us have spent long, monogamous decades with companionable husbands who provided economic security and support in the rearing of our children. When the marriage formula also included loving companionship and the thrill of romance, you're more likely to reach beyond bereavement and look for someone who can help you restore the emotional intimacy you've lost.

For women of a certain age the dating field is so narrow that it's hard to find a barely companionable man. Older women significantly outnumber older men, and those men who are available are likely to be widowers searching for a reflection of their lost but not forgotten wives. They will be awash in attitudes and habits shaped by decades of interaction with someone who is not you.

Finding a man with whom to continue life's journey depends on your ability -- and his -- to compromise. But as burdened with baggage as both of you are, it's hard to leap blithely onto the train. How to find contentment together when you're schlepping all that cargo?


Baggage is the sum of life's experiences, their effect on the psyche. Baggage determines how a potential partner will react to people and circumstances. It's easy to become excited by a relationship that's unfolding in private -- he's a skilled lover, a good cook, a fan of your favorite cable program. But is he considerate to waiters, courteous to strangers, resilient when situations don't measure up to his expectations? It's not a good idea to get all warm and cuddly with a new man before you see how he behaves in a social setting.


We must get over the cruel fact that we do not have the svelte, shapely figures we had in our twenties. An age-appropriate guy is unlikely to have washboard abs or abundant hair. The man who will make you happy will be self-aware, tactful, and will not be looking for Scarlet Johannson. He will be fine with -- will LOVE -- your expanded waistline, your not-so-perky breasts, your laugh lines, your wrinkles. These men exist.


You want a man with HOW MUCH money? Forget the dream of full support, of a credit card with his name on it. A well-managed career and a comfortable income are indications of a man's will power and common sense. Besides, at our age we should have our own nest egg. Sharing expenses is a good plan, but we are mature, experienced women, after all, and we'd cherish a man who's eager to splurge, even just occasionally, at a lavish restaurant. Having said that, I urge you to avoid the other extreme -- the skinflint. He will destroy your self-confidence and limit your fun, and those restaurant outings will be confined to Chipotle.


Your future will be just plain grim if you tie up with a man who lacks a sense of humor. And by "sense of humor" I don't mean a tendency to laugh uproariously at other people's jokes. The kind I mean depends heavily on the ability to laugh at oneself. Lightheartedness is also a hedge against the irritation senior couples inevitably feel when they come face to face with each other's annoying habits and perceived imperfections.


When you find an interesting man, you want to get to know him, and a senior man's story will include the sharing of his life with a significant other. If he talks too much about the splendors or torments of a previous relationship, particularly on a first date, be wary. Don't count on these recitations ending once he gets it off his chest. When the time is right, a peek inside the closets in his home will tell you volumes. If his wife has been absent for years and her clothes are still hanging there, you may not be as close to magic times as you think you are.


It's natural for a man to wait a while before introducing you to his family and friends. How long you can wait for this form of validation depends not only on the limitations of your patience but on how prepared you are to introduce him to your own family. The most successful scenarios are those in which it is a mutual decision, both of you deciding to somewhat simultaneously reveal your choice of one another. If you pick up some negative vibes from the kids (yours and/or his) you'll need to rethink how - and if -- you're going to cope. Kids' opposition has destroyed many senior relationships.

Sienna Jae Fein blogs at