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How to Date a Widow or Widower (It’s Really Not Scary!)

As both a grief recovery expert and a widow with more than her fair share of post-widowhood dating experience, I have been interviewed, written about and presented countless workshops on dating after loss. Since I firmly believe that should a widowed choose it, dating, companionship and love can again be a part of life, I have made it one of my missions to help the widowed find their way back into the World of Dating.

However, it was a non-widowed gentleman who recently helped me realize that I have inadvertently omitted a very important component of dating education: How does one date a widow or widower?

This gentleman was so concerned about asking a widow out that he took the time to write and ask:

“I recently met a widow and I really like her a lot. I want to ask her out to dinner and get to know her better, but I’m scared of saying or doing something wrong and inappropriate. I don’t want to be offensive. What do you think? Can you give me some tips on how to date a widow?”

I was touched that this gentleman was so concerned about his prospective date’s feelings that he would ask for advice. With the help of widowed who share their experiences (as well as one or two of my own), following are helpful suggestions for dating the widowed [bracketing is added for clarification]:

Please Don’t Be Afraid

While at a synagogue function, I met a gentleman who appeared to be interested in me… until he inquired as to my marital status. When I told him that I was widowed, he physically took two steps backward. He was literally backing away from me! The first words that came out of my mouth before I could stop myself were, “Really, it’s not contagious”. Sad to say, while he was the first encounter who behaved in this curious manner, he was not the last.

I assure you that the widowed are not scary. Talking to widowed is not scary. Spending time with a widowed is not scary. You will not catch a severe case of Death by being in a widowed person’s space. Embrace the fact that you are in the presence of a person who has survived one of the worst experiences imaginable and possesses more strength than many will ever realize.

Don’t Take “No” Personally

Terry S. was asked out by a gentleman from her church who knew that she was widowed. What he did not know was that she was just not ready to date at that point. Explains Terry, “I felt so bad saying no to him but I knew that I wasn’t ready to go out with him or any man. I was just getting back to going out with my friends. I hadn’t even gone through [my husband’s] things. What’s very sad is that after telling him no, he never spoke to me again.”

The bottom line here is that the “when” of dating again is as individual as there are widowed in the world. Some widowed are ready to date soon after their loss, others wait for years and some choose not to date at all. Still others believe themselves to be ready, give dating a try and discover that they are not quite “there” yet. “Yet” is the key word. Just because someone is not ready today does not mean that they will never be ready. If you are told “no”, do not take it personally. Remain on friendly terms and who knows…that “no” may turn into a “yes” one day.

Keep It “Light”

For the first few dates, keep the date light as to mood and surroundings. Kimlee P. shares, “I’d just started dating again after Ben died and I was only interested in casual dates. One guy took me to a very expensive restaurant on our first date. It was supposed to be very romantic I guess, but it was overwhelming. I didn’t go out again with him after that because I was scared of what he was expecting.”

Don’t misunderstand. Dimly lit restaurants with candlelight and flowers, servers in tuxedoes and strolling violinists are great – later on. Too much romance too soon can equal too much pressure – on both parties. A Sunday morning coffee or brunch, a lunch date or meeting for happy hour after work are all great ideas for the beginnings of dating.

Respect Boundaries.

Amy** had a date with someone who wanted to know the details of her husband’s death…all of them. “My husband was murdered and it took a long time before I started going out again. I got up the courage and went on a fix-up [blind date]. All he wanted to talk about was the murder – who found him, how it happened, the trial and everything else I was trying to put behind me. I cried for days after that and it was a whole year before I was brave enough to try [dating] again.”


Inquiring as to how a widowed lost their beloved is fine. In fact, it is a question that we are accustomed to answering. However, most widowed will answer that question very generally as we do not want our time with you to become all about our loss. Regardless of how a widowed lost their spouse, any ghoulish curiosity that insists on pressing for further details borders on the cruel. Accept whatever details are given, remembering that our loss was extremely painful and rehashing is not something in which we prefer to be constantly engaged. If and when a widowed is comfortable with providing more specific details, they will do so without being cajoled.

Be Patient

With rare exception, most of the widowed that I have encountered proceed slowly into dating and relationships. The reasons are many – fear of losing again, fear of getting hurt, reconciling the past with the present and future…the list goes on. Whatever their reason, you must respect the widowed’s timeline. If he or she is reticent to move ahead emotionally and/or physically, you must understand and honor their feelings. Patience, compassion and understanding are key – and when you show all three, you and your heart may be richly rewarded.

Loss is Not Funny

Let’s face it. Death is not exactly a fun, toe-tapping, lighthearted subject and attempts at humor can be one of those “nervous reflex” things, an effort to lighten the mood or assuage discomfort with the subject. However, a widowed’s loss is not funny and any attempt to make it so is not OK.

One (of many) first date/ ast date combos in my dating past involved an outing with an Australian gentleman (who proved that a cool accent does not always work). As is commonplace, he asked how my husband passed away. When I replied that Mike suffered from Lou Gehrig’s disease for over two years, Mr. Aussie replied, “He must have been one hell of a baseball player to have Lou Gehrig give him his disease”. The fact that Mike never played baseball in his life is inconsequential. The comment was grossly misplaced and insensitive.

Lesson: The words, “I’m so sorry” are really quite sufficient. Please leave the funny to professional comedians.

(A quick P.S.: Sometimes the cool accent does work. When I remarried, it was to an Englishman).

Relax…You Do Not Have to Fill Anyone’s Shoes

Call it anthropological curiosity. Call it abject boredom. Whatever the reason, a couple of years ago, I found myself watching a “How did this get so popular” television show, wherein the object is to meet someone, ostensibly fall in love and commit to a lifetime of marriage, all within a time span of approximately eight weeks.

My heart went out to one of the participants who had decided to venture back into the world of possibilities after losing his wife. The young lady for whose affection the gentleman was “competing” listened to his tragic story, and in response looked balefully at him and not-so-sympathetically groaned, “Boy, I would have some big shoes to fill”. It was moments later that this young man who had courageously stepped back into the dating world was unceremoniously booted off of the show.

When I made the decision to begin dating after my husband’s death, at no time did I pull out any figurative shoes for anyone else to fill. Why?

People are not replaceable.

Dating, companionship and love are not about shoe-filling or trying to be a replacement for someone and something that you cannot be. In other words, the only shoes that you should ever be interested in filling are your own. Do not expect the impossible of yourself – because no widow or widower is expecting it of you.

Don’t Be Threatened

It often comes as surprise to both widowed and non-widowed alike that grief and joy can occupy the same heart space. Love does not end with death, nor should it. Your widowed date can still love a departed spouse while making room for new people and experiences – including you. You need not feel threatened by memories. You are the present. You may be the promise of potentially wonderful new memories. Concentrate on what today is and what tomorrow might bring.

Should you progress into a relationship, keep in mind that a widow or widower has dates on the calendar that they may wish to commemorate (particularly if children are involved); including birthdays, anniversaries and the “angelversary” (the anniversary of a loved one’s death). Allow them the emotional room to observe what they wish, in the manner that brings them the most comfort.

Keep an Open Mind and Heart

Most importantly, keep your mind and your heart open to possibilities. Do not eliminate dating someone based upon their widowhood, no matter when or how that widowhood occurred. Being widowed shapes a person – it does not define them.

Happy dating!

**Name changed at the contributor’s request in the interest of privacy

Carole Brody Fleet is the award-winning author of the #1 ranked new release in its genre, “When Bad Things Happen to Good Women…” (Viva Editions, April, 2016). She is also the author of “Happily EVEN After… “(Viva Editions); winner of the prestigious Books for a Better Life Award, one of the top national awards in publishing; as well as the critically praised, national bestseller, “Widows Wear Stilettos…” (New Horizon Press). A contributor to the iconic Chicken Soup for the Soul series, Ms. Fleet regularly appears as a media expert on numerous television and radio programs nationally and internationally; as well as in national and international print media. To learn more, please visit and


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