I was widowed for six years before deciding to date again. So, I have a few thoughts for those of you who may be asking — what concerns, if any, should I have about dating someone who has lost their spouse?
In other words, what red flags should I look for when dating a widow or widower?
I know people who marry just months after losing their spouse, while others choose never to date or remarry. I fully understand that attitude. I had a wonderful marriage lasting 38 years, with five great children and precious memories to cherish forever. Though widowed at 59, I was content. I told myself I didn't need to be married for my senior years to be fulfilling and satisfying.
When I decided to start dating and join Catholic Match, my initial criteria involved only searches for widows. Why? I thought we might understand one another since we shared a common experience — grief. But what I learned after being on Catholic Match for a year was that no matter your background (widowed, single, divorced), we all have life experiences that have shaped us and molded us into who we are today. That’s a diplomatic way of saying we all bring emotional baggage into a relationship. The reality is that as a widow or a widower, we have our own emotional burdens that we must address before we can ever be a suitable candidate as a marriage partner.
Processing my grief and ultimately deciding to enter the dating pool took time.
To be respectful to any future marriage partners, I knew I had to resolve some issues before I could be good dating material. While I have a ton of memories to cherish, I knew I needed to be fully present in any future relationship.
Remember that people process grief differently, and its duration and intensity vary. Grief never truly disappears, but time provides distance and perspective. More importantly, time helps us cherish the past while fully engaging the present. That’s a crucial understanding for anyone who is widowed.
What issues did I face, and what issues should be on your dating radar?
Take it from this widower, here are the behaviors to look out for when dating a widow or widower:
- Unresolved grief. The grief of losing a spouse has not yet been fully processed. When my mother lost my dad, she grieved for four years before passing away. Just two years later, I lost my wife to cancer. Determined not to follow my mother’s grief experience, I faced my grief head-on and accepted it as a normal response to loss. However, people with unresolved grief often continue to feel an overwhelming sense of loss and may exhibit feelings of guilt, shame, or anger. Do not think you can “fix” them. Someone once suggested I forget the past and live in the present. On the surface, this might seem like good advice, but I had no intention of forgetting my late wife. I found it insulting for someone to suggest such a thing. However, I eventually reached a point where I could cherish those memories without becoming obsessed with them. After years as a widower, I remarried. That day, I pledged my love, fidelity, and commitment to my wife. Fortunately, my late wife had told me it was okay to marry again. She wanted me to be happy. Besides, she knew I needed someone to look after me and keep me out of trouble.
- Replacement spouse? When someone loses a spouse, their life is completely disrupted. Suddenly, they have to do EVERYTHING—laundry, mowing the lawn, cooking, paying bills, and more. Not to mention, they are now celibate (or should be). So, it’s tempting to find a new spouse quickly to replace the one they lost so that life can feel normal again. The widowed spouse is simply seeking a “replacement” for the partner they lost. If you notice your widowed dating partner pushing for a quick marriage or feeling pressured to rush the relationship, you might consider asking to slow things down a bit.
- Constantly talking about the late spouse. If your dating partner can't stop mentioning their late spouse, that is a sign of unresolved grief. Their comments might be complaints or nostalgic memories; either way, their late spouse shouldn't be a frequent topic of conversation.
- Comparing you to a late spouse, whether it’s a slip of the tongue or an ongoing habit, it’s a clear sign to be cautious. If you hear “Well, my late Sally did it this way,” think of it like a check engine light in your car—your relationship might soon need some fixing, maybe with a mechanic (counselor). When I fell in love with this adorable Irish girl on Catholic Match, I noticed how different she was from my late wife. They were so distinct in many ways. The differences weren’t good or bad, better or worse—they were just different. I valued those differences. The one thing they had in common? They both inspired me to be a better man.
- Rushing intimacy. I remember how strange it felt when I first started dating again after losing my wife, to have to put the brakes on sexually. Dating meant respecting boundaries. If the widowed dating partner is pushing for such intimacy, you'd better establish clear boundaries fast. If your not-until-marriage attitude turns off your date, consider the break-up the best decision you have ever made.
- Feeling guilt about opening their heart to someone else. I know some widowed individuals view a second marriage as if they are cheating on their late spouse. While those emotions are understandable — don’t dismiss them — the widow or widower needs more time to heal from their grief. I was a faithful husband to my first wife — until death parted us. My commitment to faithfulness lasted throughout our marriage. And now, in my second marriage, I am dedicated to honoring that vow to my current wife. As mentioned earlier, my late wife gave me permission to marry again. What a gift that was. It allowed me to enter any new relationship without feeling guilty.
- Lack of transparency. During your dating period, as you and your partner get to know each other, you should start sharing genuine feelings and find it easier to discuss the past and present. Getting to know the real you, and vice versa, means opening up and having meaningful conversations. If your widowed dating partner struggles to share such details, you may need to be patient, as some people are genuinely hesitant to be vulnerable. However, as the relationship progresses and your date continues to deflect or keep parts of their lives hidden, it might be time to reevaluate where the relationship is headed. Are your conversations shallow or meaningful?
- Children’s blessing. Gaining the blessing of children in any remarriage situation is important — especially when dealing with a widow or widower. The children have lost a mother or father. Depending on how long their surviving parent has been widowed and the age of the children, they may see a step-parent as a replacement. Take the time to get to know the children and, hopefully, earn their blessing to marry their surviving parent. Otherwise, family drama could take over your new marriage.
I saw a meme recently that read, “Dating when you are older is like finding a shopping cart with good wheels at Walmart.” I tend to believe that most widows or widowers have much to bring to a new relationship. Our wheels may be a bit squeaky, but nothing a little WD-40 (love and attention) cannot fix. Being aware of the red flags mentioned above highlights the wheels that may not be ready to be fixed…yet.
