An Unlikely Couple: Grieving and Dating: How to Get Started is committed to helping people deal with their grief by encouraging them to write to their deceased loved ones as a form of self-therapy. That said, we do want everyone who uses to be able to move on with their life. This series of articles is for those who have lost a spouse or significant other and want to find love and companionship again.

I will share the authorship of this article on grieving and dating with my wife, Wendy. We plan to give widows and widowers a view of both sides of the equation as a couple who have been through it successfully. Here’s the backstory: I lost my wife of 22 years when I was 45. We were childless and seeking to adopt the year before she died. A few months earlier Wendy lost her husband of 10 years when she was 37 leaving her with two young children, then ten months and four and a half years. What we shared in common was we both had clearly defined objectives—she wanted not only a husband but also a father for her children. I wanted a wife, but also wanted to raise children.

Young widowers and widows may share these objectives. In middle age a split arises. Widows often want someone to be a father to their children; many of the men have already done so, and aren’t in love with the idea. There’s a fundamental inequity in dating as people age; men hold most of the marbles. There are far more available younger women who are single, divorced or widowed than there are available men. There’s a cognitive dissonance in the minds of middle-aged men: they are programmed by nature to be attracted to younger women. We often think it’s about looks, but in fact it is about fertility. The dissonance is that they probably already have children of college age or beyond and don’t want to take advantage of a younger woman’s fecundity.


LARRY: My first piece of advice to men of a certain age is think this through carefully. Understand that throughout your life you are programmed to be attracted to the young and fertile, but unless you really want to raise a first or second family, get over it. Young women who tell you they don’t really want to have kids are at best often kidding themselves and at worst, deceiving you. Despite their best intentions, many young women have a change of heart about having children as their biological clock ticks down. You should date women who are age appropriate. This applies at all ages.  If you are 75 and feel great and are dating women in their early 60s, think about this: in ten years, they she will still feel great and you’ll be 85. Now take a look at the 85 year old men around you. It’s better to be in phase age-wise with your mate.

WENDY: Suddenly, single I found myself unsure of whom I was, and had to work thru an unexpected personal rediscovery period, a second adolescence of sorts. It was unsettling for I thought I had finished with all of that years ago. This enabled me to evolve unencumbered by expectations and patterns of my former life as Allen’s wife. Thanks to Allen, I would be dating as a 37 years old physician and mother of two. I felt more powerful and able to see potential mates for what they were and weren’t. I trusted my gut a lot more than when I was in my early 20’s. I did what I wanted to and made decisions for all aspects of my life that formally I would have first consulted my older physician husband Allen about. 


LARRY: Let’s talk about when to start dating. The circumstances of your loss are a key factor in this. There’s a difference between what I experienced and what others go through.  Vanessa’s death came after years of preparing ourselves for the possibility and nine weeks in the hospital at the end; through most of those nine weeks we had the opportunity to achieve resolution and closure. For those who have lost someone in an accident or sudden death, the healing process is very different. I was ready to date early because first, I had a purpose. I wanted children and wasn’t getting any younger, and second, I had gone through three months of grieving ‘rehearsal,’ and over two months of living alone while she was hospitalized. Also, her final spoken words, mentioned above, liberated me to pursue a new marriage without guilt.

The problem with getting into it early is that the people who can fix you up have preconceived notions of what that timing should be, ranging from  six months to a full year. Many of the women you might date share this sentiment. It’s like rebound dating; women don’t want to be the first one you’ve dated after a breakup or a loss. It rarely works out.

WENDY: Start dating when you feel you have a grasp on who you are. I met my first husband when I was 24 and married at 27 and had defined myself through my relationship with him. Once alone I had to rediscover who I was and what I wanted before I began dating.  My only other advice is to not consider anyone else’s time line for when to start dating. This is your life. If you want to have children with someone else then your biology may help you decide when to start dating.


LARRY:  You should have a clear objective in dating and be forthright about it. It makes it easier for people to fix you up, and leads to far fewer awkward situations. Shortly before I met Wendy I dated a woman with young children who had lost a husband to cancer. She had clear objectives and didn’t hesitate to articulate them. She had met her husband when she was 14 and he 15 and he had been the only man in her life. Before settling down again, she wanted to ‘play the field’ for at least two years. I was equally clear; I wanted a soul mate and children; I was open to adoptive parenting because of my age and the presence unfortunate genes in my lineage.

WENDY: Women come from another universe, and mothers have their own cosmic view. I was 37 when my husband of ten years died suddenly.  I had an eleven month-old son and a four year-old daughter.  I carried my family’s loss as my own, identifying more as a single mother than a widow. My concerns were for my children’s emotional development and ultimate happiness in their lives. Setting “us” rather than “me” as a priority I began the process of finding a man who wanted to be a father. I put an ad in New York Magazine—the of its time–starting it with “My children are my greatest assets. They could be yours too.” Each potential date was screened with my mother antennae. I needed to be honest with myself and really clear about what would be right for us, my children and me. I didn’t want more children because I was 37 and I didn’t want my children to feel like outsiders. Although I wanted a man to be a father to my children I wasn’t so sure that I could love someone else’s children without feeling that I was betraying my own. 

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