Widower Wednesday: Dating a Widower Chapter 1

I need your help. One of the most frequent topics I’m asked to write on is how to deal with the feelings of being compared to the late wife. As you know, the late wife often becomes a saint once she passes on. Sometimes she was a saint in real life. Either way it’s common to feel like you’re competing against a perfect person and being held to a high standard of perfection by the widower and/or his/her family and friends.

I’ve tried several times to write on this topic but don’t feel like I’ve done the topic justice. As a result, I’ve never posted my thoughts on that matter. This is where you come in. I’d like you to email me your stories on how you've dealt with feeling like you’re competing with a saint or things your widower had done to make you feel that he loves you for who you are. (I’ll use a pseudonym if you don’t want your first name published). Again, this is one of the most common topics I’m asked to write on so your story could help a lot of women. I’ll include a few thoughts as well, but I’d rather have the focus be on you and your stories. All I ask is that you keep the email to 500 words or less and let me know if you want your real first name used or for me to come up with an alias. So send me an email. If you want to see a Widower Wednesday column that contains past contributions from readers, click here.

Thanks in advance for your help.


This week I’m publishing the introduction and first chapter from the upcoming Dating a Widower book as well as the story's from readers that I accepted. The manuscript is just going through typesetting right now for those who want a hard copy. eBooks (Kindle and Nook to start with) are ready to go live once I push the button. Look for an official announcement soon.


You've met a man that knocks you off your feet. Everything about him is perfect except for one thing: He’s a widower. And that makes you pause. Is he ready to move on and start a new life with me? Is he done grieving? If the relationship works out, will he love me as much as the late wife? These and a thousand other questions go through your head. Well, you’re in luck.

The purpose of this book isn’t to discourage you from dating a widower. Rather, it’s to 1) give you insight into the heart and mind of a widower so you can better understand his behavior and 2) help you decide for yourself if the widower you’re dating is ready to start a new life with you, or whether he’s just looking to fill the hole in his heart.

As a widower who has since remarried, I’ve seen too many men (myself included) start dating before they’re emotionally ready to make serious commitments to the women they claim to love. I’ve also corresponded with hundreds of women who have fallen in love with men who claimed to be ready to move on but, in the end, were not. Most of these women could have avoided heartache if they’d been aware of the red flags.

The good news is that there are many widowers out there who are ready to make room in their heart for another person. As I write this, I’ve been married to Julianna for eight years. I also personally know many other widowers who are happily remarried. We know how fortunate and blessed we are to have someone else we can spend the rest of our lives with.

I hope the widower you’re dating is one of those men.

Abel Keogh August 2011

Chapter 1: Widowers—They’re Still Men!

Widowers are men. It doesn’t matter how long they were married, how their wife died, or how long it’s been since their wife passed on—widowers act, think, and grieve like men. There are no widower issues—only man issues.

When you think of widowers as men, you can better understand the motivations and reasons behind their actions and decide for yourself whether he’s ready to move on and start a new life with you, or simply looking to fill the hole in his heart or for someone to warm his bed at night.

When it comes to men, there are five things you need to know about them that affects their behavior after they’ve lost a spouse.

  1. Widowers Have an Internal Need for Relationships
  2. A few weeks after my late wife, Krista, and I were married, we had dinner with her grandmother, a widow. During dinner, her grandmother told us that a neighbor and good friend had recently passed away after a long illness. After we expressed our condolences, her grandmother told us how the woman’s husband had stopped by to invite her to the funeral. After she told the man she planned on coming, the man had then told Krista’s grandmother he’d be calling on her soon.

    Krista and I were floored. How could anyone even think about dating someone else when their wife wasn’t even buried yet? On the way home from dinner that night, I told Krista that if she died, I’d never remarry. Krista gave my arm a squeeze and told me she felt the same way.

    Two years after that conversation, Krista committed suicide. In the months following her death, I found myself wanting to date again. I felt guilty for having these feelings. I thought there was something wrong with me; perhaps I was angry at Krista about taking her own life, and as a result, I was trying to get even with her. But the desire to date again grew stronger with each passing day. Finally, I gave in to the feelings and signed up with an online dating site and went on my first widower date a few weeks later. Later I met a wonderful woman named Julianna. We fell in love and were married 15 months after Krista died. (As I write this, we’re a month shy of celebrating our eighth anniversary.)

    It wasn’t until after I remarried and started researching how men grieve that I realized my desire to date again so soon after Krista’s death was natural. After losing a spouse, most widowers find that the richness and purpose life once held is gone. Their life feels broken, and they want to fix it. The most logical way to do that? Find another woman. And while there’s nothing wrong with dating months or weeks after a spouse dies, most widowers who start dating again are still grieving the loss of their spouse. They’re not emotionally ready to make long-term or serious commitments to the women they’re dating.

    Unfortunately, this doesn’t stop widowers from telling the women they’re dating that they love them and are ready to start a new life. A lot of women end up falling in love with widowers, only to end up with a broken heart after the widowers unexpectedly tell them they’re not ready to move on.

  3. Widowers Will Stay in Relationships with Women They Don’t Love
  4. Because widowers have a strong desire to be in a relationship, they will get serious with women they don’t really love. Most widowers are just happy to have a woman in their life again. Often, their loneliness is so acute that they’ll attach themselves to the first person who shows the slightest interest in them. Having someone who will hold them and tell them how much they’re needed or loved will overcome the nagging feeling in the back of their mind that the relationship isn’t right—at least for a while.

    Sometimes it’s hard to tell which men are serious about moving on and which are just looking for someone to lessen the ache in their hearts. Both types of widowers will treat you like a queen, tell you how much they love you, and do other things that make you feel like the center of their universe. However, widowers who aren’t serious about starting over with you can only fake these relationships for so long. Sooner or later, the doubts that have been nagging them since they first became serious with you will overwhelm their desire for companionship. Once they reach that point, those widowers who still have a shred of manliness in them will tell you the relationship isn’t working out and end it.

    Soon after I started dating, I became serious with a woman I’ll call Jennifer. We were friends before I was married to Krista, and after her death, we reconnected. I flirted with her, started dating her, and eventually told her I wanted to spend the rest of my life with her. During our relationship, I never loved Jennifer—at least, not in the way you need to love someone to spend the rest of your life with them.

    When we were together, I couldn’t see myself marrying or having a family with her. Despite these reservations, I didn’t want to lose her. Having Jennifer in my life brought a sense of normalcy that had been missing since Krista died. Having someone at my side was better than having no one. Eventually I ended the relationship, but it came at a high price. I lost a good friend, and Jennifer ended up with a broken heart and confused feelings.

    If you want to avoid giving your heart to a man who’s not ready to move on, my advice is to take things slowly—especially in the first few months of the relationship. It’s also a good way to learn if the widower is looking for a long-term relationship or looking to fill the hole in his heart. A widower who sees a potential long-term, committed relationship with you will be fine taking things slow. He’ll patiently wait for you to be ready while finding ways to prove his feelings for you. If he’s just looking for sex, companionship, or a therapist, he’ll push you to speed things up, threaten to date other people, or quickly lose interest in the relationship.

    When a relationship is new and the guy seems like a great catch, it’s very easy to get emotionally swept up the moment and overlook possible warning signs that he’s not ready to open his heart to you However, taking things slow when it comes to physical or emotional intimacy is a small price to pay in order to avoid getting your heart crushed.

  5. Widowers Pursue Women They’re Interested In
  6. Men, by nature, are pursuers. When the right woman catches their eye, they’ll do just about anything and everything they can to show the woman how much they love them.

    The same is true for widowers. When widowers find someone they truly love, they’ll put aside the grief and make you the number one person in their hearts and minds. Widowers who are ready to move on will voluntarily take down photos of the late wife, remove the wedding ring, and make you feel like the only woman he’s ever loved. Nothing will stop them from starting a new life with someone else—including their grief. It may not happen overnight, but you’ll see steady progress from the widower and have little doubt that he’s making room in his heart for you.

    The best way to tell if a man is interested in pursuing you is to give him a chance to take the lead in the relationship. Let him plan dates and other activities, and let him initiate most of the communication. Doing this accomplishes two things. First, it forces the widower to decide how serious he is about you. A man who has doubts about the relationship will eventually grow tired of having to prove his love to someone when they aren’t really interested. Eventually he’ll end it.

    Second, this helps him make room in his heart for you. Widowers prove their love through actions and sacrifice. The more they can prove their love through actions, the easier it is for them to develop the deep love needed to put their grief aside and start a new life. Without this deep love, it’s extremely difficult for him to make room in his heart for you.

    I want to make one thing clear: There’s nothing wrong with setting up dates or calling him. I’m not saying you have to let him initiate everything. But if you find yourself doing most of the heavy lifting in the relationship, it’s easy for him to simply go along for the ride instead of deciding if the relationship is right for him.

    There’s a part of me that believes I never would have gotten serious with Jennifer had she let me take more of the lead when we started dating. Because of the doubts in the back of my mind, I hesitated to set up dates and other activities once it became clear that there was a mutual interest in taking things forward. Jennifer, however, had no problem taking the lead. And I had no problem letting her. After all, it felt nice to have someone who wanted to be at my side as often as possible. All I had to do was tell her that I loved her and wanted to spend the rest of my life with her. I never really had to prove those feelings because Jennifer was eager to take charge.

    Julianna, on the other hand, behaved in the opposite way. In addition to having a somewhat shy personality, she also had a lot of concerns about dating a widower and was hesitant to get involved with someone whose late wife had only been dead six months. It quickly became obvious that the only chance I had at winning her heart was to prove to her that I was ready to make her number one in my heart. It took about three months of dating before she felt comfortable becoming serious with me.

    During that time, I did everything I could to show her that I was ready to start a new life with her. And in the end, I not only proved my love to her, but proved to myself that I could heal from the loss of a spouse, open my heart to someone else, and love that person just as much.

  7. Men Can Only Actively Love One Woman at a Time
  8. Most women wouldn’t get involved with a divorced man who was still angry and bitter toward an ex-wife or a single man who was still anguishing over a failed romance. Yet many women will fall in love with a widower who’s still mourning for his late spouse. These women usually believe that if they’re patient and are there for him while he grieves, he’ll eventually move on.

    Nothing could be further from the truth. While the human heart has a great capacity for love, widowers can only actively love one woman at a time. It doesn’t matter if the woman is alive or dead; they can only devote their thoughts, feelings, and attention to one woman. If they’re constantly thinking about the late wife, they won’t be able to do what it takes to move on and love someone else.

    In order to move on, widowers need to focus their time, energy, and attention on you, instead of the late wife. This means that their utmost thoughts and feelings are on you and your happiness, and not on how much they miss the dead spouse. Widowers who are truly ready for a long-term, committed relationship won’t have a problem taking this step.

    Some widowers can give you their full attention for a short time. For example, when I dated Jennifer, I was able to focus my attention and thoughts on her when we were together. However, when I wasn’t in her presence or talking to her, my thoughts quickly returned to Krista and the life we had together. As a result, I was never able to find a place in my heart for Jennifer.

    I didn’t have that problem with Julianna. In fact, I couldn’t get her out of my mind. My thoughts and attention were always focused on her and her happiness. Because I was so focused on Julianna, I became less and less focused on my loss. This made it easier for me to lock up my love for Krista and make room in my heart for Julianna.

    Don’t be afraid to end a relationship with a widower who can’t make you number one in his heart and mind. Better to cut your losses than waste your time competing with a ghost, because the ghost will always win.

  9. A Widower’s Actions Speak Louder than Words
  10. A widower will tell you that he loves you, that you’re pretty, and will say other sweet nothings in order to get attention, sex, companionship, or anything else he wants out of the relationship. A widower’s desire to plug the hole in his heart is often so intense that he’ll tell you whatever he thinks you want to hear because it feels good to have someone by his side again.

    Don’t listen to a widower’s flattering words. Instead, focus on his actions. If you go to his house and her clothes are still in the closet, her pictures are all over the walls, her ashes are displayed prominently, and her voice is still on the answering machine, it doesn’t matter how many times he says he loves you and wants to spend the rest of his life with you. He’s not ready to move on and start a new life. If a widower really loves you, his actions and words will align.

    When I dated Jennifer, my words and actions never matched up. I told her she was the center of my universe, yet there wasn’t one photo of her hanging up at my house. I told her that she was number one in my heart, yet I constantly found myself talking about my late wife, instead of our relationship. I said I wanted to have a future with her, but hesitated in telling my family and friends that I was even dating her.

    It wasn’t that way with Julianna. I was quick to put photos of her up all over the house. I constantly talked about the life, future, and family I wanted to have with her. I couldn’t wait to tell everyone—even complete strangers—that I was dating the most wonderful woman in the world. My actions and words were one and the same. I told her she had the number one spot in my heart, then went out and proved it to her every single day.


Stories of Women Dating Widowers Ann’s Story

I hesitate to call our courtship and marriage a success because I don’t see love and long-term relationships in the black and white manner of women’s magazines or dating self-help books. Success is relative even if failure is painted with a universal brush.

When I asked my husband, Rob, why he thought we succeeded when other couples in our situation fail, he replied only half-jokingly, “It was my stellar personality.” That’s not quite true, but it’s not entirely incorrect, either. Relationships that work depend on both partners wanting them to do so.

When we met, I had been widowed for 11 months. Rob’s wife had died four months earlier. While I’d begun dating, he’d decided to wait to give himself time to recuperate from Shelley’s death and the months he’d spent taking care of her.

We cultivated a “just friends” relationship, which began with meeting via an online widowed support board and eventually took itself offline using email, IM and the telephone.

Rob was the one who suggested elevating our friendship to dating. Before that I was content, despite knowing that our relationship was a bit flirtier than “just friends.” However, I didn’t try to analyze his actions or read between his words. Like any man, Rob said what he meant, and his actions spoke just as clearly. If a man is interested, he tells you, and if there is a potential long-term option, he acts.

Both of us being widowed probably made things easier. I didn’t have to wonder how he felt, nor did I take anything related to his grief personally. Our relationship was a separate issue. Grief is not a couple's activity, and it’s not an obstacle to moving on with someone else. The right person is more motivation than any widower needs to pack up the past and build a new life. If new love stirred grief up, it was acknowledged, and then we moved on. If he’d hemmed and hawed or had thrown up continual roadblocks in the form of his late wife, children or in-laws, I would have known that he wasn’t really serious about us.


I used those things to put off suitors who didn’t interest me or with whom I saw no potential for a long-term relationship. It’s easier than saying, “I’m not that into you.”

Does grief come up? Yes, but only a little bit. If a widower loves you, grief won’t derail what you have together. With time, patience and shared effort, you can build a lasting relationship just like any couple does.

Rob made it clear that I was his priority. He was considerate of his daughters’ conflicted reactions to us but did not let their grief dictate his decisions. He let family and friends know that he was a grown man who knew his own mind and heart. Not that we met with much active interference or criticism. Most people expressed support and genuine happiness for us.

Bottom line is that our actions set the tone for our children, family and friends. We knew what we wanted, acted accordingly and whatever issues came up were discussed and dealt with immediately—just like any other healthy relationship. Widowed people fall in love, and they do live happily ever after—again.