15 Relationship Tips on Dating a Widower Over 50

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Dating a widower over 50 can be tricky business. 

It can also be extremely rewarding, resulting in a long-term relationship. Clearly, dating in your 50’s and beyond is much different than the early, heady years of our teens, twenties, or even thirties! 

I don’t want to speak for everyone in my age group, but I’m definitely not impressionable anymore. I suspect we may be alike in that area. 

The reality is that we’ve experienced a lot of life by the time we get to be 50 and beyond. The loves, losses, lessons learned, and even our regrets are part of our physical and mental makeup.

Let’s face it, it takes a lot of courage for anybody in our age bracket to hit the dating scene. Adding grief and loneliness to the equation doesn’t make it any easier. 

The process of grieving, healing, and opening up to a new relationship is deeply personal and can vary greatly between individuals.

This blog post is designed for people considering dating a widower over 50. You might already be in the relationship and have some questions. 

Maybe you’re interested in someone whose spouse recently passed and you’re not sure how to approach the situation.

Keep reading for insights, advice, and practice tips on how to navigate this delicate balance!

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Understanding the Grief Process When Dating a Widower Over 50

Grief is an obvious and normal shift in reality that hits all of us at some point(s) in our lives.

There’s no getting around it. Wouldn’t it be great if we all followed the same journey through grief with a set beginning and end point? Of course, we all know it doesn’t work that way.

In reality, the stages of grief are messy.

They’re not linear. In fact, a person can circle around all five stages many times, over the course of years in some cases. In my experience, time smoothes the jagged lines of grief, but it doesn’t necessarily take it all away.

I don’t entirely believe that “time heals all wounds”. Time, I think, just makes the wounds more tolerable.

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There’s no right or wrong way to grieve

I know that losing a dog isn’t the same as losing a spouse, but it’s been two years and I’m still grieving the loss. It’s like having a permanent bruise that hurts when you press on it. 

I’m sure that I felt many of the same things any grieving person would feel. 

I felt guilty for wanting to get another dog right away. I was afraid of loving another dog because I knew, eventually, that dog would also pass away. 

I also worried about what other people would think about me getting another dog so quickly. When you compare that to the loss of a spouse, it’s easy to point out the similaries. Guilt. Fear. Shame. Uncertainty. It’s all there!

Only the person grieving can tell you when they’re ready to move on. 

So, in terms of dating a widower over 50, it’s important to keep the five stages of grief in mind, be patient, and realize that the person may have gotten through all five stages, but they’re about to circle through again.

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The Five Stages of Grief

I’m sure you’ve heard this before, but I think it’s important to recap the five stages of grief. Again, they’re not linear. There’s no order to how or when will appear. 

Denial

Denial, the first stage of grief, acts as a protective barrier for a grieving widower. It’s as if your body knows it can’t handle the grief all at once, so it allows a temporary reprieve. 

It may appear as avoidance of conversations about the late wife, clinging to routines or belongings as if nothing has changed, or insisting everything is fine despite clear emotional pain. 

Recognizing denial as a natural response can foster patience and empathy during this fragile phase of healing.

Anger

Anger, a common stage of grief, often emerges as frustration or resentment toward the loss, the deceased, or even the circumstances surrounding it. 

It might show as irritability or lashing out at others. Bitterness about the unfairness of the situation can also surface.

Recognizing that anger is a normal way to process pain can make it easier to approach this phase with patience and understanding.

Bargaining

Bargaining is a way people try to make sense of their loss, often by looking for ways they could have changed the outcome. 

It might sound like “What if I had done this differently?” or “If only things had gone another way.” 

Understanding this stage can help you stay patient as they work through these thoughts.

Depression

Depression is when the weight of the loss really sinks in, often bringing feelings of sadness, loneliness, or hopelessness.

It’s a tough phase, but giving space for these emotions can help them move toward healing.

Acceptance

Acceptance is about coming to terms with the loss and finding a way to move forward. It doesn’t mean forgetting but learning to live with the grief while still creating a new and meaningful life.

Understanding the stages of grief will help you better understand whether the recent widower is ready for a serious relationship. 

When is the ‘Right Time’ to Date Again?

The answer to this question can only be answered by the widower. 

The “right time” is different for everybody. Things that can hold people back include worrying about what family will think, a sense of “cheating on” their dead spouse, nerves, and much more. I’m not sure when it happened, but at some point in history some parts of society decided a person had to remain a widower for a full year before it was acceptable to date again.

Maybe people didn’t fully understand the complexities of grief back then. The reality is that it varies from person to person. Dating after the death of a spouse is tricky business and not for the faint of heart! This is especially true if you worry about what other people might think.

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The Reality of Dating Apps for New Widowers

I’m 57 years old, and I can’t imagine having to face the dating scene again, let along navigate dating apps. As a lifestyle blogger for people over 50, I’m happy to say I’ve discovered good sites geared specifically to seniors. 

I can emphasize with widowers facing this dating reality in the 21st century. In some ways, I suppose there is some safety in browsing through profiles. Actually meeting a stranger in an attempt to forge (hopefully) a long-term relationship has to be nerve-wracking. 

Have you met widower through a dating app? What was your experience? Let me know in the comments!

I can understand how a widower might try a dating app as a litmus test to see whether they’re ready to date or not.

For example, they might jump in with every intention of having a first date only to second-guess the decision.

As the person on the other side of the dating app, you might end up feeling confused, especially if this individual is too hesitant to date, backs out of a date, or stands up a date entirely.

Senior Dating Apps

If you’re interested in learning more about senior dating apps, and which ones you can browse for free, check out my latest blog posts on the subject:

29 Free Dating Profile Examples for Females Over 50 

First Date Etiquette for People Over 50

7 Smart Ways to Browse Plenty of Fish Without Signing Up    

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Try SeniorMatch

A premium dating site for seniors!

Telling Family and Friends About the New Relationship

Let’s jump ahead and assume the widower has decided to take the leap. You’ve met and things seem to be going well.

Congratulations!  

Of course, it there’s any chance of this turning into a long-term relationship, you’re going to have to meet their family. This means making a good impression on any adult children, close friends, or mutual friends who knew the late spouse.

The reality of dating a widower over 50 is that they’re going to come with baggage. We all do. We’ve lived! We’ve experienced many things! Going into a new relationship with that understanding will go a long way.

Dating a Widower Over 50 Can Be a Delicate Endeavor 

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Introducing a new partner can be a delicate and emotional step for a widower. These relationships often come with a shared history and strong emotions tied to the loss. Naturally, this makes the introduction of someone new a potential source of discomfort or even conflict. 

Adult children may feel awkward

Adult children may feel protective of their parent or worry that the new relationship diminishes the memory of their deceased parent. Similarly, mutual friends may struggle with how to balance their loyalty to the late spouse while welcoming the new partner.

Take time to understand the dynamics and approach introductions with care.

Respect any hesitation or mixed emotions, as they’re a natural part of the adjustment. Let the widower lead the conversations, as they’re best suited to explain the new relationship. Staying open and supportive can help ease the transition.

Red Flags That a Widower Might Not Be Ready to Date

It’s normal for a widower, especially a recent widower, to speak about their deceased spouse. They have, after all, shared a life together.

Memories are bound to trickle to the surface now and then. There comes a time, however, when enough is enough. It’s not a sign that you’re not good enough, it’s a sign that he isn’t ready for a serious relationship yet.

The following behaviours could be signs that he’s not ready to jump into a new relationship yet:

Frequent Comparison to Late Spouse

One sign that a widower may not be ready for a new relationship is frequent comparisons to their late spouse. Sure, it’s going to happen from time to time. That’s natural. 

Your intuition will tell you if there’s a problem. You’ll feel it in the way your partner constantly brings up how you’re so different from his spouse. He will either praise or lament those differences.

If you start feeling undervalued in a relationship, it may be time to move on.

Gently express your feelings and let them know how these comments affect you. Encourage open dialogue to help them reflect on whether they are emotionally ready for a new relationship.

Still Deeply Grieving

Intense and ongoing grief is another sign that a widower may need more time before committing to a new relationship. 

They may regularly express sadness, talk about their loss as though it just happened, or appear consumed by their grief. In this case, giving them space to process their emotions is essential. You might suggest professional counseling to help them work through their pain. 

Late Spouse’s Belongings Are Untouched

​It’s normal to have some keepsakes or a few photographs around the house. But if it feels like the late spouse might actually still be alive, it could be a warning that he’s not ready to move on.

For example, her clothes may all still be hanging in the closet or there’s a vanity covered with her perfume, makeup, and jewelry. A home that feels like a shrine to a late spouse can indicate that a widower is holding on tightly to the past.

He hasn’t done anything wrong, and shouldn’t be made to feel that way. However, it could be a clear sign that he isn’t remotely ready to be dating. Open the lines of communication gently. Ask how he feels about integrating you into his life. 

This can provide insight into their readiness to build a new chapter and whether they’re open to making space for a new partner.

Reluctance to Introduce You

If a widower avoids introducing you to family, friends, or anyone from their late spouse’s life, it could be a sign they are not ready to fully embrace the new relationship. 

This is less about you, and more about his fear of judgement or uncertainty about how others will react. 

Having an honest conversation about their reluctance can help you understand their emotional state. Patience may be needed, but it’s also important to assess if this hesitation suggests deeper issues.

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Guilt About Moving On

Dating a widower over 50 could mean helping him struggle with guilt about dating again. He may feel that doing so is a betrayal of their late spouse. 

​Signs that a guilt conscience is at play include the following behaviors: 

  • Frequently expressing regret about dating again or feeling like they’re betraying their late spouse.
  • Hesitating to fully commit to the relationship or make future plans.
  • Avoiding introducing you to family or friends out of fear of judgment.
  • Making comments about what their late partner would think or feel about the new relationship.
  • Over-apologizing for pursuing a new relationship, even when there’s no need to do so.
  • Seeming preoccupied or distant during significant dates tied to their late spouse.

Inability to Discuss Future Plans

After dating a while, it’s normal to share ideas about the future together. However, if the person you’re dating steers the conversation to other topics, it might be a sign they’re not ready to move forward.

Gently ask if they see themselves creating a future with a new partner. Their response can provide clarity about their readiness for a deeper relationship.

Excessive Mention of Anniversaries

Widowers may focus heavily on significant dates related to their late spouse. I don’t think you’d be human if you didn’t have thoughts and feelings about your beloved when anniversaries and birthdays roll around, especially in that first year after the death.

However, if it continues in an excessive, overly emotional way, it could signify a lingering emotional attachment. Of course, it’s important to be supportive. However, you might want to watch for signs of depression. If this is the case, try gently bringing up the topic of grief counselling.

Strong Resistance to Change

A widower who resists adjusting routines or traditions tied to their late spouse may not be ready for a new relationship. 

This resistance could reflect an unwillingness to move forward. Openly discuss how their reluctance makes you feel and whether they’re willing to compromise. Their willingness to make adjustments can indicate their readiness to embrace a new chapter.

Seeking Reassurance Constantly

Widowers who frequently seek validation that they’re making the “right decision” by dating may be struggling with unresolved emotions.

While it’s natural to have doubts, constant reassurance-seeking can signal deeper uncertainty. Encourage them to trust their instincts and make decisions without relying on external validation. Building confidence in their choices is an important part of healing.

Friends and Family Are Overly Protective

Sometimes, a widower’s close circle may express concerns about them dating or even compare you to the late spouse. This dynamic can create tension and make it difficult to move forward. 

Openly discuss these challenges with your partner, but recognize that they may need to address these issues with their family or friends independently. It’s important for the widower to establish boundaries and affirm their readiness for a new relationship.

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Ending the Relationship If It’s Not the Right Fit

You know in your gut when something isn’t right. After you’ve exercised patience and encouraged open communication, there may come a time when you need to have a heart to heart discussion. 

The widower’s unique emotional needs may simply be too much for you to handle. Once it becomes clear that the widower isn’t ready, it might be time to cut ties. 

It may sound harsh, but the reality is that the widower is likely stuck in a torrent of feelings. Guilt. Anxiety. Sadness. It’s hard to maintain any relationship when you’re wracked with grief. 

15 Relationship Tips on Dating a Widower Over 50

When dating a widower over 50, it’s important to remember the stages of grief. More importantly, it’s important to understand that a person can loop through those grief stages multiple times. 

However, if you’re interested in pursuing a widower over 50, I’ve put together some tips to help guide you through the early stages of your relationship. 

1. Be Patient with the Dating Process

The dating process after loss requires time and understanding. Rushing can lead to emotional overwhelm or unresolved grief surfacing.

2. Communicate Openly About Their Past Experiences

Encourage open communication about their late wife and past relationships. This builds trust and fosters a deeper connection.

3. Understand Their Unique Challenges

Recognize the complexities of widower relationships, including lingering emotions tied to significant dates or shared memories.

4. Respect Their Emotional Needs

Widowers might need additional emotional support during the early days of a new relationship. Offer a listening ear without judgment.

5. Don’t Compete with Their Late Spouse

Accept that their late wife will always hold a special place in their heart. A healthy relationship allows for love to coexist without competition.

6. Be Mindful of Significant Dates

Birthdays, anniversaries, and other significant dates related to their deceased spouse might bring up emotions. Show compassion during these times. Perhaps they’d like to be alone during these milestones or maybe they just need to feel comfortable mourning their loss.

7. Gauge Their Readiness for New Experiences

A widower truly ready to date will be open to building new memories and sharing new experiences with you.

8. Avoid Pressuring for Physical Intimacy

Respect their comfort zone when it comes to physical intimacy. The transition to a senior sex life can take time.

9. Look for Signs of True Love

Focus on whether they treat you as the most important person in their life rather than a consolation prize.

10. Take Note of Pictures and Mementos

Discuss how they choose to incorporate memories of their late wife into their life and home. Balance is key.

11. Introduce Yourself to Close Friends Gradually

Building a rapport with their close friends and mutual friends can strengthen your relationship and ease social transitions.

12. Handle Adult Children Carefully

Be prepared for varying reactions from adult children. Respect their feelings while reinforcing your intentions with kindness.

13. Be Open About Your Own Journey

Share your past experiences and emotional needs to build mutual understanding and foster a healthy relationship.

14. Embrace New Connections and Memories

Focus on creating a fresh start together while honoring their past relationships in a healthy way.

15. Seek Support When Needed

If challenges arise, consider seeking advice or resources from experts like Abel Keogh or Tom Blake, who specialize in widower dating information.

Abel Keogh and Tom Blake are authors and experts who have written extensively about relationships, particularly focusing on the unique dynamics of dating and relationships involving widowers.

Summary: The Delicate Balance of Dating a Widower Over 50

Dating a widower over 50 comes with unique challenges, including lingering grief, guilt, and fear.

Open communication, patience, and empathy are essential for building a strong connection.

By respecting each other’s pasts while focusing on the present, couples can create meaningful and fulfilling relationships that honor the journeys that brought them together.

What are your experiences with dating a widower over 50? Let me know in the comments!

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