21 Dos And Don’ts When Dating A Widower

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Of all the complex relationship zones that you enter, dating a widower is perhaps one of the most challenging. It is unlike being with a long-term bachelor or divorcee. At the outset, it may seem like a smooth situation. After all, he is single, knows what it is to be in a committed relationship and his life experiences may have arguably made him a more sensitive and kind person.

However, despite the advantages, there are certain problems to be aware of as well. Dating a widower and feeling second best is one such challenge that you must brace for. Despite all the challenges, the odds that you’d find a widower on the dating scene, especially if you’re making a fresh start yourself, are quite substantive. Statistics suggest that 61% of men are ready for a new connection by 25 months after their spouse’s demise.

So, if you end up connecting with a widower and really hit it off, how do you make sure that things don’t go south? For that, you have to bear in mind that the rules and regulations of dating a widower are quite different, and if not followed, things can prove to be quite disastrous for you and for him. So, let’s do a deep dive into the expected behavior of a widower in a new relationship, so you can navigate this situation like a pro.

21 Dos And Don’ts When Dating A Widower

Dating a man who has lost his spouse or long-term partner can present a unique situation for any woman. The biggest worry, of course, is that he may not have gotten over his deceased spouse, which may lead you to worry if he will be able to love you the way you deserve to be loved. Or would you be stuck dating a widower feeling second best?

If you’ve ever wondered why is dating a widower so hard, this could be a key reason. Despite being romantically involved with him, you may feel that special place in his life and heart is already taken. Or you may be left to deal with the emotional consequences of sleeping with a widower who is not ready to open his heart and his life to someone new. At the same time, you cannot let such apprehensions hold you back if you truly like him and he feels the same way about you.

Truth be told, anything is possible and each relationship is different. Whether you’re dating a young widower or someone who has been left behind after sharing decades with his spouse, the key is to keep an open mind and let your relationship take its own course. That said, there are some dos and don’ts that may help you negotiate this tricky area so that even if you end up with one, you don’t end up feeling insecure about dating a widower.

Related Reading: 20 Rules Of Dating A Single Dad

1. Don’t probe too much

The first and most significant rule when you begin a relationship that has the potential to grow is to avoid asking too many questions about his dead wife. At least, let the first few dates pass by without bringing up the subject. Get to know him better and let him open up about his past; don’t get too personal too soon.

He may come across as an emotionally unavailable widower if you touch a raw nerve too soon and try to access parts of him that he may not be ready to reveal yet. Remember, that grief is not linear and takes its own trajectory. He could well be grieving his wife’s death and looking to make a fresh start at the same time. Building intimacy with a widower can take time and patience is your best ally.

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He may act all closed up and distant if you try to get too close too soon. You may find this behavior of a widower odd considering you’re trying to build a romantic relationship with him, but to him, this may just be a coping mechanism. So, be prepared to take things slow and give him the time he needs to let his guard down.

2. Be prepared to listen

Even if you don’t probe too much, be prepared to listen. When dating a widower, the way to win his heart is to be open to hearing stories about his past life. He might have had a happy marriage and perhaps might not have gotten over her. Surviving the death of his wife must have been devastating for him.

It takes immense courage to pick up the pieces and start afresh. If he is willing to talk, encourage it. Let him know that you are willing to accept that she will forever be a part of his life. When he talks about his deceased wife with a strong fondness and a sparkle in his eyes, don’t get too caught up in the “dating a widower feeling second best” mindset.

If you make him feel like you’re competing with his dead spouse for his attention and affection, that’s when a widower pulls away. So, if you’re genuinely interested in him, don’t go there. However, if his wife is all he can talk about and you feel as if you’re at the receiving end of emotional dumping you didn’t sign up for, then he’s clearly stuck in the past. Don’t overlook such red flags when dating a widower.

3. Realize that you will be fighting a memory

While it depends on the nature of the relationship he shared with his spouse, on some level it would be difficult for him to move on. Especially if his loss is a recent one, the presence of his dead wife might loom large and cause a shadow in the new relationship as well. Don’t expect him to fall headlong into love too soon.

Become his ally in his journey of processing and coming to terms with his grief rather than turning it into an ominous word in your relationship. Doing so will help you develop a deep and meaningful relationship with your partner. At the same time, don’t overlook any potential red flags for dating a widower.

As we said before, if all he does is talk about his deceased wife and wallows, it’s a warning sign that he is still too deep into the grieving process. He may be looking to date as a distraction from the pain or to compensate for missing physical intimacy after the death of a spouse, and that’s not what you deserve. And definitely don’t rush into sleeping with him. If you’re both not on the same page, you may end up suffering the consequences of sleeping with a widower who isn’t emotionally invested in you.

4. Take it slow when dating a widower

Dating a widower can’t follow a “hi, hello, let’s get together” trajectory. It might be easy to get to date him but not very easy to get him to commit or fall deeply into a relationship. Remember you could be dating a widower who is not ready for a serious, committed partnership just yet.

Give him time and let the relationship take its own course. Our advice is to take it really slow, step by step. Especially if you fancy an emotionally unavailable widower, you might have to work harder to take it forward. Be patient in the relationship and be prepared to take things forward at a pace he’s comfortable with.

You can avoid a myriad of relationship problems with a widower later on if you focus on building a strong foundation now. So, if you truly fancy him and see that he reciprocates your feelings, be open to taking things one step at a time. Be mindful of the fact that he is dealing with the setback of surviving the death of his wife, and you need to navigate this situation with compassion and empathy.

Related Reading: What You Must Know About Dating A Divorcee

5. Understand his trauma

The death of a loved one can be a traumatic experience. In many cases, when the death has been due to an unnatural cause, the pain is deeper. Just see how hard it is to forget someone you loved deeply even in the event of a breakup or divorce. In the case of the death of a spouse, it’s a lot harder. If it was a happy and healthy relationship, surviving the death of his wife is undoubtedly the hardest thing he’d have dealt with.

In such a scenario, small triggers can bring back painful memories. Be mindful of this to be able to understand the behavior of a widower and empathize with him. When dating a widower, don’t feel offended if you are at the receiving end of a few emotional reactions to tiny triggers. These aren’t essentially red flags signaling you to stop. It’s just an outpouring of grief that will settle down over time, or at least become more manageable.

6. Don’t be at the receiving end of his guilt

It is one thing to understand his pain but quite another to be with a man who refuses to move on. Like a breakup hits guys later, the sorrow around the demise of a spouse can have the same impact. He may have entered the dating arena but if he inadvertently compares you with his ex or talks about her death constantly, know that you might be dating a widower who feels guilty subconsciously.

You will have to take a call on how long you want to date a man who is stuck in the past. Dating a widower who is not ready can be a lost cause. Think long and hard about whether it’s worth your while to invest in him emotionally. You cannot build intimacy with a widower and look forward to a lasting relationship if he is not fully prepared to let you in. Keep an eye out for these red flags when dating a widower.

7. Don’t judge his dating habits

why is dating a widower so hard
Don’t judge a man who is still grieving but wants to date

Apollonia Ponti, dating coach, says there is no right or wrong time to start dating for a person who has lost his significant other. “The process of grief for each person is different. So don’t judge a man by how he enters the dating field after he has lost his partner,” she advises.

Some people may have been prepared for the inevitable and might grieve less, others might be seeking a new relationship to get over their loneliness. Men feel very lonely be it after the death of a spouse or a divorce. When dating a widowed man, it’s best to leave your judgment at the door. Go in with an open mind so that you can embrace who he is and what he has to offer.

Whether you’re dating a young widower or someone older, don’t presume what brought him back into the dating game. Is he dating because of missing physical intimacy after the death of his spouse? How could he be looking to date so soon after surviving the death of his wife? Questions like these will only color your judgment and make you view him from a narrow lens, so steer clear of them as far as possible.

Related Reading: 11 Expert Tips To Have A Successful Second Marriage

8. Communicate well when dating a widower

What do widowers want in a woman? There can’t be a one-size-fits-all answer to this question, and only the man you’re with can tell you what he is looking for in a potential partner. The only way to get to understand his dating goals and expectations is by communicating well. There might be a long gap between getting to know him and being in a serious relationship with him but throughout the process, do not hold back from expressing yourself and asking the right questions.

Keep the channels of communication open all the time, more so if you feel insecure or worry that he may not love you the way he loved his spouse. Talk it out to know the extent of his feelings for his deceased spouse and his feelings for you. This is especially crucial if you’re with an emotionally unavailable widower and you’re both looking at the possibility of a long-term, stable relationship.

Even when a widower pulls away, don’t just let the whole thing fizzle away without an open and honest conversation about what both of you want from this connection. Communication is the key to resolving most issues and deadlocks, and your relationship problems with a widower are no exception. Prioritize fostering honest, open and unbridled communication in your connection; it will help cement your bond.

9. Befriend his children

The behavior of a widower in a new relationship can tell you a lot about his intentions. One of the signs a widower is serious about your relationship with him is when he introduces you to his children. If you love him truly, make all attempts to befriend his kids. If marriage with the widower is on the cards, then it’s time to start working on your relationship with the stepchildren.

Now, this can be a delicate situation and you have to be prepared for both, hostility or openness. Either way, you can become closer to your man by showing him you are up for the challenge and can win over his children. But at no point should you insinuate that you’re going to take their mother’s place. That can backfire, putting your relationship in jeopardy.

10. Handle his former in-laws carefully

Handling his children is one thing but if the family has been close-knit, it’s quite possible that he would still be in touch with his deceased wife’s family. While his association with them might be a comfort factor for him, the same cannot be said about their equation with you, unless they welcome you wholeheartedly.

You may choose to distance yourself from this extended family if you are uncomfortable. Unless there is open hostility on that front, try to make an effort to at least have a pleasant association with them before you give up and choose to keep your distance. It’s understandable if you’re feeling insecure dating a widower who still treats his deceased wife’s family like his own.

You can feel like an outsider and second-guess your place in his life. However, if he is taking the step of introducing you to that part of the family, it’s a positive sign. He is prepared to let you into his life wholeheartedly and wants you to be a part of his innermost circle. Sometimes, changing your own perspective of the situation is all it takes to navigate the twists and turns of how to date a widower.

Related Reading: Second Marriage After 40 – What to Expect

11. Don’t hesitate to seek his help

If the two of you are planning to take your relationship to the next level, do not hesitate to seek his help and advice in getting you to be accepted by his family and children. Whatever be his situation or past grief, it is his responsibility as your partner too to get you to be more comfortable around his kids and family.

Work on it together with a sense of compassion and sensitivity, don’t do it alone. Remember that one of the biggest relationship problems with a widower can be gaining the trust and acceptance of his children and family. While you will have to make an effort on that front, as your partner, he’s got to have your back every step of the way.

This becomes all the more crucial when you’re dating a young widower and have to find a way to carve out space for yourself in his family. Young children can put up greater resistance to the idea of someone else filling their mom’s shoes (even if that is not your intention, it can be hard to explain that to a child). You’re going to need your partner’s unflinching support to get through this, so don’t hesitate to ask.

12. Get to know what he wants

There is one big advantage of dating a widower, says Apollonia Ponti, and that is the fact that mostly, they are very sure of what they want. “A person who has seen the death of a special someone is usually clear about their relationship needs. They may want a similar love story or they may want to do new things,” she says.

Simon, a 56-year-old former US Navy veteran, maintains that while he is open to dating, he doesn’t see forming a connection as intimate and intense as he shared with his wife. “Even if I get into a relationship, it will be from a distance. I can never love anyone the way I loved my wife. I guess I’m looking for companionship, more than love.”

The answer to how to date a widower can be hidden in what the person you’re with is looking for. Use this to your advantage as you get a rather clear picture of what you are entering into. As we’ve said before, there can be no singular answer to, “What do widowers want in a woman?”, and being intuitive and attentive to his needs is your best bet at understanding what he seeks from your connection.

13. Do not have high expectations

When you enter a relationship with an older man who has been widowed after years of marriage, his experiences and expectations might be vastly different from yours. Even if the two of you connected on various aspects, building a new relationship might not come too easy for him.

The grief may get in the way, preventing him from forging a meaningful and deep connection with you. Or perhaps, he may just be at a stage in life where love and relationship mean something entirely different than it does to you. It’s best if you are realistic about your own expectations. This becomes that much more crucial if the age gap is significant.

While the behavior of a widower in a new relationship or a budding romantic connection will tell you a lot, don’t just rely on your perception of his behavior to assess what he wants. Instead, communicate openly and honestly about managing expectations and setting boundaries in your relationship so that there is no scope for ambiguity.

Related Reading: 11 Things That Attract A Younger Woman To An Older Man

14. Don’t try to step into his ex’s shoes

Guess what can bring relationship problems with a widower? Trying to fill in his deceased spouse’s place by submerging your own personality to match that of his ex’s! When you are dating a widower, never think you are filling a void in his life. Also, ensure that your boyfriend isn’t looking for someone to do that.

While you can be empathetic to his loss, do not stop being your own person. At the same time, don’t expect him to erase the memory of his former wife and go about living this new chapter with you as if she never existed. Accept that there is enough room in his heart to miss her and love you at the same time.

There may be certain aspects of his life and personality that are and forever will be tied to his deceased spouse. His children, his lifestyle, his beliefs and values, to name a few. You have to learn to build something new with him around these existing facets and not upon them if you want to avoid feeling insecure dating a widower.

15. Never talk badly of his wife

how to date a widower
Never talk badly about his deceased spouse

Dating a widower is not easy and it is possible that you might get irritated at times by the inadvertent comparison. He might go back into the past more often than you wish. But even in those moments, never ever make the mistake of badmouthing his former spouse.

There would be times when you would have an argument or two but take care not to bring his past or his deceased spouse into it as it will only make matters worse for both of you. If you do that, the argument would spell doom for your relationship. No matter how angry, enraged, hurt, or disappointed you are, never lose sight of how hard surviving the death of his wife must have been for him. Take care to never trigger that grief just to get back at him.

These are exactly the kind of circumstances when a widower pulls away. The only way to avoid it is to not be in competition with a person who is no longer around. Instead, focus on your present and your future with him. Dating a widower becomes a lot easier when you’re not constantly looking at him from the prism of his past.

16. Expect intimacy issues with a widower

Once again, it depends a lot on the nature of the relationship and the period of loss but physical and emotional intimacy with a widower can become an issue at least initially. Unless the man is completely ready for a new relationship, he might find it difficult to connect with another woman emotionally.

Do not judge him for that, just give it time or talk to him about intimacy issues. If these intimacy issues persist, convince him to seek professional help from a sexologist or a therapist, depending on the nature of the disconnect. Building intimacy with a widower will require consistent effort and copious amounts of patience from you. Of course, he has to be willing to meet you halfway, otherwise, you’re fighting a losing battle.

Related Reading: Dating In 50s – 15 Tips To Do It Right

17. Watch out for the red flags

One of the red flags that you must be aware of is when a widower pulls away from you the moment you talk about getting serious in the relationship. Or when you feel he is hesitant to introduce you to his family and friends. You end up in a push-pull relationship then.

This clearly shows that either he is not fully into you the way you would expect him to or he is still not over his past marriage. Only you can decide how long you would want to wait before he finds the courage to make it official with you. Do not brush these red flags for dating a widower under the carpet because they will return to haunt you and cause you even more pain down the line.

Acknowledge and accept any issues that you may see in your budding relationship with a widower, and decide how to handle them keeping your best interests in mind. Ignoring the red flags when dating a widower just because being with him feels good in the moment won’t do either of you any good.

18. Don’t allow pictures or memories to make you insecure

One of the most common problems faced by women who are dating a widower is how to react to a person who refuses to erase his late spouse’s presence, be it in the form of pictures or memorabilia from the house. Honestly, you shouldn’t even attempt. It is totally okay to display pics of their late partner, it does not mean they love you less.

Claire, who started dating a widower, felt extremely conflicted by the fact that his home was still aflush with memories of her. There were photos of them everywhere, and she asked a friend, “Should I suggest that he take down her photos, so that our relationship can truly feel like a new beginning?”

Her friend, who had also lost her husband recently, warned her against it, saying that even a hint to that effect could threaten the relationship. Claire heeded the advice and made peace with the fact that he didn’t have to erase the past to make room for their future together.

19. Learn to give a widower space

While every relationship has issues, some challenges are unique to dating a widower. For instance, some dates can be painful – the death anniversary, his spouse’s birthday, their wedding date, children’s birthdays and so on. Be aware of these moments and allow him space for mourning.

Let him know that you are in tune with his feelings. Sometimes, giving him space itself can be a lovely gesture on your part. If he wants to be left alone for the day or spend time at his wife’s grave all by himself, give him a peck on the cheek and tell him you will be here waiting for him. Or that you’re there for him, if and when he wants to share his feelings with you.

Don’t take his emotional investment in the past as an affront to your partnership. The two can be independent of one another. Just because he has you to share his life with now doesn’t mean that he can erase the memories of the past. You can’t compete with a dead person nor should you have to. You get to share your present and future with him whereas what he shared with his wife is already in the past. So, don’t let insecurities get the better of you.

Related Reading: 12 Signs Of Unconditional Love In A Relationship

20. Ask some important questions

If you find yourself falling in love with a widower after a period of serious dating, yet are not sure where you stand in his life, do not hesitate to find out your status. There are things you need to talk about with your partner and it’s best to have the seemingly awkward or difficult conversations early on than keep ignoring the proverbial elephant in the room.

Relationship coach and author Abel Keogh lists three questions: “Do you love me?” “Are we in an exclusive relationship?” and “Where is this relationship going?” Answers to these basic questions will give you the information you need to know to proceed further or not,” he says.

Sure dating a widower can be different from other relationships you’ve had, but you still need to know where it is headed and if you’re both on the same page about what the future holds. Irrespective of how he feels about it, don’t hold yourself back from broaching this topic once you’ve been together for a considerable time.

21. Build new memories

While dating a widower, the best way to get over any feelings of insecurity is to build new memories with your partner. Perhaps he will remember or miss his spouse during special occasions like festivals and birthdays. You should never compete with his ex but you can certainly make life beautiful by doing things he likes, your way.

Holidays and celebrations can take place in a way that does not bring back the painful past, rather it gives you both new reasons to smile. You can build new traditions and customs that are yours and yours alone, and don’t have the shadows of the past looming large over them. Perhaps, mix up the Christmas dinner menu a little or volunteer for a good cause on Thanksgiving. When you make new memories together, the “dating a widower and feeling second best” insecurities will begin to fade away.

Dating a widower requires pretty much the same qualities as dating anyone else – understanding, patience, love and emotions. However, what makes it different are the circumstances. Perhaps a different kind of maturity will be required and if you master that, being with a sensitive widower can be a beautiful experience.


1. What to know about dating a widower?

When dating a widower, know that you will never be able to erase memories of his ex-wife, you may even find yourself competing for attention especially if he constantly talks about her.

2. Why is dating a widower so hard?

Dating a widower is hard because the process of grieving is different for each person. The death of a loved one is a very difficult pain to get over and depending on the circumstances, a widower may find it difficult to open up or commit to a new relationship.

3. How do you know if a widower loves you?

You can know a widower loves you only if he does not compare you with his ex-wife, makes an attempt to help you bond with his family and children and is ready to commit to you exclusively.

4. What percentage of widowers remarry?

While there is no specific study, there are indications that show that widowers are more likely to get married again as opposed to divorcees. Also, it is said that widowers remarry more quickly than widows. The average time for widowers to remarry is about 2-3 years, the same for women is 3-5 years.

5. Do widowers ever move on?

Widowers might take time to move on depending on how strong their marriage was but it is in no way an indication that they cannot find love again.

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