Why I Will Never Date A Widower Again

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Of all the second chances at love, putting oneself out there and starting dating after death of spouse is perhaps the most complicated. The grief, the guilt, the pain can make it hard for a lot of people to truly embrace the prospect of turning over a new leaf and moving on. The experience can prove to be an emotional roller coaster not just for the person dating after loss of spouse but also their romantic prospects/partners. So much so that the brunt of it all can make one swear off dating someone who has lost a spouse. A woman who has had a similar experience and has vowed, “I will never date a widower again,” shares her story with Bonobology, explaining what brought her to this decision.

Let’s take a look at her story, and then explore some of the most common dating a widower red flags and challenges, and whether it’s possible to navigate them to build a successful relationship, with insights from some renowned relationship and mental health experts.

I Will Never Date A Widower Again—A Woman Shares Her Story

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When I met James, I thought I had finally found someone kind, mature, and emotionally intelligent. He was 47, a father of two adult children, and had lost his wife, Laura, to cancer four years ago. We matched on a dating app, and from the very first conversation, he was warm, articulate, and surprisingly open. He told me upfront about Laura, which I respected. He said he had grieved, gone to therapy, and was now in a place where he was ready to give love another chance.

I was 42, divorced, and had spent the last five years healing from a marriage that had drained me emotionally. It seemed like he and I were on the same page as far as healing and moving on was concerned. I wanted companionship, someone with shared values and emotional depth. James seemed like a man who had known deep love and loss—someone who wouldn’t take a relationship for granted.

dating a widower red flags — I was wrong to believe I could build a relationship with a man who hasn’t fully grieved the loss of his wife

Our first few months were lovely. He was affectionate, attentive, and made me feel seen and heard. We had many conversations about life, love, and second chances, and it seemed like our visions for the future and perspectives on the past were in perfect alignment. The fact that he had been happily married before didn’t bother me—it reassured me that he was capable of long-term commitment. I wasn’t naïve. I knew dating a widower had its challenges, but he made me believe he was ready for something real.

I was wrong.

Related Reading: The Top 5 Signs A Widower Is Serious About Your Relationship

Laura was everywhere

Slowly, I began to see that being with him meant living in the shadow of a deceased wife. The first signs were subtle. His house was still exactly as it had been when Laura was alive. Pictures of her were everywhere—not just family photos, which I would have understood, but framed portraits in the bedroom, the study, even the kitchen. Her coats still hung in the hallway. Her perfume bottles sat untouched on the dresser.

One evening, when we were cooking together at his place, I accidentally knocked over a mug, and James froze. His face went pale. “That was Laura’s favorite mug,” he said, staring at the broken pieces. I immediately apologized, feeling awful, but the way he mourned that shattered mug—it was as if I had broken something sacred. He barely spoke to me for the rest of the evening.

Over time, I noticed more things. Her car still sat in the driveway, untouched. He still paid for her phone plan because “it felt wrong to cancel it.” His social media was filled with tributes to her—on her birthday, their wedding anniversary, the anniversary of her death. I told myself this was normal, that grief isn’t linear.

But then there was his family.

how to date a widower — His life was a shrine to the time shared with Laura

His family never saw me as more than “The woman after Laura”

His grown children, 24 and 21, were polite but distant. I didn’t expect them to embrace me with open arms, but I did hope for some level of warmth. Instead, they seemed wary, as if I were an intruder in their father’s life. His mother, an elegant woman in her seventies, was even worse.

During a family dinner, she made a point of bringing up Laura constantly.

“James, remember how Laura used to make this dish? No one could ever make it like she did.”

“Oh, Laura always said the dining table should be set a certain way.”

At one point, she turned to me with an almost pitying look. “It must be difficult dating a man who had such a perfect wife.”

James didn’t defend me. He just smiled sadly, as if he agreed with her.

I should have left then, but I didn’t.

Related Reading: First Relationship After Being Widowed – 18 Dos And Don’ts

I was always competing with a ghost

The most painful moment came six months into our relationship when we were planning a weekend away. I had suggested a cabin getaway, something romantic. James hesitated. “Laura and I used to go to a cabin every year,” he said. “I don’t know if I can do that with someone else.”

That was the moment I truly understood—he’s still in love with his dead wife. I was just a placeholder. A warm body in his life. He liked me, maybe even cared for me, but his heart was still with Laura.

tips for dating a widower — I was just a placeholder

Then came the final blow. One evening, we had a couple of his friends over for dinner. One of them said, “We were surprised when James told us about you. None of us thought he would ever love anyone the way he loved Laura. But we’re glad he found you.”

To this, Jame replied, “That’s true. What Laura and I had was special. She was my college sweetheart, my partner for close to 20 years. Nothing can replace that but life has to go on, right?” He squeezed my hand as he said this, and I felt sick.

The breaking point

I confronted him about it, and asked him if he even loved me. He couldn’t bring himself to say he did. All he could muster was, “I do care about you, but…” He sighed, running a hand through his hair. “Laura and I had a soulmate connection. No one will ever come close to her.”

That was it. That was the moment I knew I was done. I couldn’t continue living in the shadow of a deceased wife. I packed my things and left.

I will never date a widower again

I will never date a widower again. Not because they are bad people, but because I refuse to be in a relationship where I am forever second-best to someone who isn’t even alive. I deserve to be loved for who I am, not for the space I can temporarily fill in someone’s grief. Never again.

Related Reading: 12 Painful Signs He Doesn’t Want A Relationship With You

Challenges Of Dating A Widower

Dating a widower isn’t like dating someone who’s been divorced or single for years. Someone who has lost a spouse they loved and hoped to walk into the sunset of life comes with a unique emotional weight. Even more so, if a person starts dating after death of spouse before they are truly ready to love again. They bring in the baggage of grief and guilt into the relationship, making you feel like you’re competing with someone who isn’t even here anymore. This translates into the following challenges of dating a widower:

1. You might feel like you’re competing with a ghost

Even if his late wife has been gone for years, she can still loom large over your relationship. Maybe it’s the way he talks about her constantly, or the subtle comparisons that make you feel like you’re living in the shadow of a deceased wife or how her pictures are still all over the house.

Say you go out on a dinner date, and he orders something, and then follows it up with, “Oh, this was my wife’s favorite.” You let it slide. Then, the first sip of wine he takes reminds him of something else about her. Then there is an anecdote about a vacation. Just like that, the date has turned into a tribute to his deceased wife, and you’re just a passive listener, wondering, “Why am I even here?”

“A widower’s heart may still be deeply tied to his late wife. If he hasn’t fully processed his grief, you might find yourself in an emotional tug-of-war with someone who isn’t physically present but still very much alive in his mind.”
— Dr. Carla Manley, clinical psychologist

2. His grief can overshadow your relationship

Grief isn’t linear, it doesn’t have an end date. Even if he says he’s “ready”, it doesn’t mean he’s fully healed. There might be days when he’s withdrawn, moody, or emotionally unavailable—especially around significant dates like anniversaries or birthdays. While you may rationally understand what he is going through, it can still be emotionally distressing to be in a relationship with someone who checks out on you from time to time.

It can seem like your life, as a couple, ceases to matter when certain sensitive days roll around or he just wakes up in a deep funk because he has a dream about his wife. You’re left feeling like an outsider in his mourning process. Psychologist and relationship coach Rachel Green explains why this is one of the dating a widower red flags, “It’s normal for grief to resurface, but if it repeatedly disrupts the relationship, it’s a sign that he may not be emotionally available yet.”

Related Reading: How I Won Over My Boyfriend’s Mom

3. His family might never accept you

Earning the approval of your partner’s family can get tricky in any relationship. But it becomes a whole different ballgame when they see you as the woman who “replaced” their beloved mother/sister/daughter/daughter-in-law. “Many families idealize the deceased spouse, making it difficult for a new partner to be seen as anything but an intruder,” says relationship expert Dr. Susan Winter.

how too date a widower — Resistance from family can add to the challenges of dating a widower

4. You might feel like an emotional placeholder

Some widowers start dating not because they’re ready to turn over a new leaf in their life but because they’re lonely. They miss companionship, affection, and someone to talk to—but deep down, they may still be in a relationship with their deceased spouse. This can stir up a lot of doubts and insecurities in your mind, and even make you question your worth as a partner.

Explaining why this poses a challenge, psychotherapist Dr. Megan Fleming says, “A widower who is dating just to fill a void will struggle to form a genuine connection. If he’s keeping his heart locked away, no matter how wonderful you are, you’ll always feel like a substitute.”

Related Reading: 11 Signs You Are Single In A Relationship

5. Special dates can be emotional minefields

You’ve been dating a widower, and Valentine’s Day rolls around the corner. You’re excited about spending the day with him, celebrating your bond, your relationship. But your partner is too busy reminiscing about the first woman he ever gave flowers to—his late wife. Instead of feeling cherished and loved, you feel invisible.

You might find him struggling with similar emotions around holidays like Thanksgiving or Christmas. Of course, his wife’s birthday, their anniversary, her death anniversary are bound to be difficult for him, but if you notice that he is in the spate of a wave of sadness even on his birthday, or yours, or your first anniversary together, these are glaring dating a widower red flags that suggest he is not even close to being ready to move on.

6. He might struggle with guilt over loving you

he's still in love with his dead wife — He may feel like he’s betraying his deceased wife by moving on

Dr. Karen Finn, divorce and relationship coach, says, “Widowers who haven’t made peace with their past will sabotage their future relationships, either by holding back emotionally or by pushing their partner away when things get too serious.” Even if he truly cares about you, he may not be able to forge a meaningful relationship because he wrestles with guilt over “moving on” or feels as if loving you would mean betraying his late spouse.

As a result, you may begin to feel as if your relationship has plateaued around the dating phase and you aren’t moving toward any significant milestones. Be it moving in together, meeting his extended family, or discussing the possibility of marriage down the road, he may just push back, saying, “I don’t know if I’m ready” or “I need more time”. This may not mean that his feelings for you aren’t genuine or he doesn’t care about you, but it will definitely feel as if you’re forcing a relationship on a person who is tied to someone else.

So, Should You Date A Widower?

All these challenges and emotional upheavals can make it seem like dating a widower is not worth the effort. However, in the realm of romantic relationships, things aren’t quite as black and white. There are usually no absolute answers. The same is true for dating a widower.

Whether or not you should explore a romantic connection with a man who has lost his spouse really depends on whether he has done the emotional work to heal and if he is ready to open his heart and his life to a new partner (and isn’t looking for a placeholder). If he can create space for a new love without living in the past, there is no reason why dating a widower cannot be the beginning of a beautiful partnership.

On the other hand, if you constantly feel like you’re second best, competing with memories, or stuck in a relationship that isn’t progressing, it’s okay to walk away. Your heart deserves to be fully loved, not just tolerated in the absence of someone else.

The Way Forward—How To Date A Widower

So, you’ve fallen for a widower. You see the red flags, you know the challenges, but you’re not quite ready to call it quits, and make the “I will never date a widower again” resolve. At least, not yet. Maybe despite the challenges, you see real potential in this relationship. Maybe the man you’re with is kind, thoughtful, and genuinely trying. A part of you wants to give it your best shot so that there are no regrets about what could’ve been.

Your thoughts are valid. But here’s the thing you need to remember: Dating a widower can work; it requires patience, emotional strength, and clear boundaries. If you care about him enough to try, these tips for dating a widower will help you find a way to move forward in a way that protects your heart, too.

1. Have an honest conversation about where he stands

Before you invest more of yourself into the relationship, you need to know if he is emotionally ready for a relationship. Some widowers think they’re ready for love, only to realize that they’re still stuck in the past. Others might not even realize how much grief is still shaping their choices.

“A widower who is truly ready to move forward will acknowledge his past without letting it dictate his future. If he avoids the topic or downplays your concerns, that’s a red flag,” says Dr. Fleming. That’s why you need clarity on his emotional state before you even begin to figure out how to date a widower.

How to do it

Sit down and ask him directly:

“Do you feel emotionally available for a new relationship?”
“How do you see your future—with me?”
“Am I someone you love for who I am, or do I just make the loneliness easier?”

If he hesitates, gets defensive, or can’t give you a clear answer, that’s your sign that he’s not ready—and you deserve someone who is.

Related Reading: How Grief And Loss Of Loved One Affects Relationships

2. Set boundaries around his grief

Yes, his late wife was an important part of his life. No, that doesn’t mean your relationship should revolve around her memory. If his home feels like a shrine, if every conversation turns into “When she was alive…” or if he shuts down emotionally on special dates, you need to set clear boundaries.

“Grief never fully disappears, but a widower must learn to balance remembrance with new beginnings. If his grief overshadows his current relationship, it’s not fair to his new partner,” says Dr. John Amodeo, a relationship therapist

How to do it

Let him know that it’s okay to talk about his late wife, but not in a way that makes you feel like a visitor in his past
If his home still feels like a museum, gently encourage small changes—maybe moving some pictures to an album instead of the walls
If anniversaries or birthdays turn into days of complete withdrawal, discuss how he can acknowledge those dates without shutting you out. For instance, instead of letting him spiral into sadness on his late wife’s birthday, suggest a quiet way to honor her together, like lighting a candle or taking a walk

However, if he continues to shut you out completely, ask yourself if that’s something you can handle long-term.

3. Make sure he sees you as a partner, not a placeholder

One of the biggest dangers of dating a widower is becoming the person who fills the void in his life rather than someone he truly loves. That can be hard to deal with. You need to know that he values you, not just your presence.

How to do it

Pay attention to how he treats your relationship.

Does he make future plans with you or does everything feel temporary?
Does he introduce you to friends and family as his partner, or just “someone he’s seeing”?
Does he show you affection without guilt, or does he hesitate as if he’s betraying his past?

If he still lives his life as a “married man”, making you feel like his side-chick, it’s a warning sign that he’s not even close to ready for a real relationship. In that case, you may be wasting your time and emotional energy trying to decipher how to date a widower.

Related Reading: Emotional Dumping Vs. Venting: Differences, Signs, And Examples

4. Have a plan for dealing with his family

His kids, in-laws, and close friends may struggle to accept you, not because of who you are, but because they see him moving on as a betrayal. You can’t force them to like you, but you can set expectations for a cordial relationship with them.

Green says, “When a widower starts dating, his family often feels like they are losing their last connection to the late spouse. The key is to give them time while also making sure your own needs are met.”

How to do it

Be patient, but don’t let them walk all over you
If they constantly compare you to his late wife, talk to your partner—he needs to step in and set boundaries with them
If his kids refuse to acknowledge you, let your partner handle it—it’s not your job to win them over

5. Know when to walk away

Love isn’t enough if you’re constantly feeling like an outsider in your own relationship, and no amount of tips for dating a widower can change that. If, despite your efforts, he’s still emotionally unavailable, his grief overshadows everything, or he just isn’t capable of giving you a full relationship, it’s okay to walk away.

“Staying in a relationship where you feel unseen, unheard, or like a second choice will only damage your self-worth. A widower who is truly ready will show you, not just tell you.”
—Dr. Susan Winter, relationship expert.

How to do it

If you feel more like a caretaker of his grief than a partner, it’s time to reevaluate
If he still refers to his late wife as “the love of his life” and struggles with guilt over moving on, that’s not a relationship you should have to fix

If you’re constantly waiting for him to be ready while neglecting your own needs, ask yourself: Am I happy in this relationship?

Key Pointers

Dating a widower can feel like competing with a ghost, as memories of the late spouse often overshadow the new relationship
Grief is not linear, and unresolved emotions can make a widower withdrawn or emotionally distant, leaving the new partner feeling neglected
The widower’s family may struggle to accept a new partner, seeing them as an intruder or a replacement for the deceased spouse
Some widowers date out of loneliness rather than genuine readiness, making the new partner feel like a temporary fill for emotional voids
A successful relationship requires emotional readiness and clear boundaries; if grief dominates, it’s okay to leave and prioritize self-worth

Final Thoughts

Dating a widower isn’t easy, but it can work if he has truly healed, is willing to make space for you, and respects your emotional needs. If you feel valued, loved, and like you’re building something real, that’s a relationship worth fighting for. But if you’re constantly feeling sidelined, can’t shake off the feeling that he’s still in love with his dead wife, or waiting for him to be ready, remember this: You are not a backup plan. You deserve to be someone’s first choice.

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