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Dating a Widower – Everything You Need to Know

Dating a Widower – Everything You Need to Know

Updated on Oct 16, 2023

Reviewed by Julianne Cantarella, MSW, LSW , Certified Relationship Coach

Dating a Widower – Everything You Need to Know

Dating a widower is no crime or something to be ashamed of. A man who lost his spouse is equally entitled to find the love of his life again, just like any other single man! 

If you happen to be the one he is interested in, and you like him too, do not think twice. Go for it!

You may ask, will it be easy for you to adjust to this relationship? Will you be able to live up to his expectations? A simple answer to this is – that you will never know until you try.

Dating a Widower – 10 Things to Know

Dating a widower is full of challenges just like any other relationship. And just like any other relationship, you need to nurture it and give it time to grow.

It is always a good idea to do a little homework about anything new you are about to begin. In this case, it will be wise to understand the dynamics of dating someone whose wife passed away.

Let us have a look at the basic things you must know before dating a widower…

1. Don’t be too curious

A man whose wife passed away recently may not like to be interrogated about her. It may just rub salt into his wounds.

So, be patient and allow them the space to share the story. Remember, it takes time to get to know someone.

So, don’t push them, or else he might get skeptical about this new relationship and withdraw himself from you.

2. Be yourself

Remember, this is not a competition. His late wife and you are two different individuals. It is useless to try to fill a void left by his late wife. The best thing you can do is be his comfort and calm.

If you try to show that you are a better choice than his late wife, you might just hurt him more and ruin everything you both have built so far!

3. Do not rush

Be patient with him and yourself.

His grief may feel like a burden, but you must allow him the time to cross the bridge to be with you. Try to match up to his pace.

He might take longer to get comfortable with you. Do not be pushy. Nurture the relationship with kindness and patience. You will not be disappointed.

4. Pay your respects well

After losing a spouse, it is natural for a man to keep talking about his dead-wife. It is difficult for him to let go of old memories. It may take months or weeks, or even years, to finally move ahead in life.

So, never get annoyed whenever he brings up his previous spouse. Instead, always acknowledge his pain and love for his late wife. Pay respect to his deceased wife with comforting words like – “She must have been a wonderful person” or “I am sorry for your loss”.

5. Don’t be hypersensitive

It may take a while for him to get comfortable with you. In the process, he might often affectionately bring up his wife in your presence. Do not be jealous or offended. Remember, he does it unknowingly.

With time as he builds new memories with you, these things will, too, die a natural death. If you get too sensitive at the mention of his previous spouse, he might just call it off for good!

6. Tread lightly when it comes to kids

This can get very tricky. If your man has kids from his previous marriage, you need to be patient with them too. The relationship should be strong enough before you introduce yourself to his kids.  

They might not accept you as their mother but try to be good friends with them and see how things go.

7. Set realistic expectations

Do not get upset if your man keeps moving back and forth between his grief and you. It’s natural for a widower to have emotional baggage. Be his good friend and a shoulder to cry on before anything else.

Once he comes to terms with his present, the dating scene will gradually change for the better for both of you.

8. Watch out for the red flags

Keep your eyes open for all the wrong signals. Make sure you are not his rebound and that he is genuinely interested to take this relationship forward.

If he constantly compares you to his late wife or if he doesn’t acknowledge you enough in the relationship, those are the bright red flags you need to pay attention to and save yourself from further humiliation.

9. Never bad-mouth his late wife

This is a complete no-no when you are dating a widower. You may not necessarily like his late wife or her style or anything related to her. But never speak a word against her.

Be very cautious when angry and be mindful not to use undesirable language to criticize his late wife and his relationship. Your man will walk right off.

10. Allow him to grieve on special occasions

Certain days of the year may have a special meaning for your widower partner – be kind enough to ask if he wants you to be by his side during such hard days.

If he wants to be alone, let him be and do not overthink the situation. He just needs time to be by himself to process his emotions and has got nothing to do with you. 

Pros and cons of dating a widower

Dating a widower is a whole different ball game. A widower’s reactions to the dating process don’t always follow the same patterns as those of single men. But no matter how a widower perceives dating, you must analyze every aspect of the situation before jumping into it.

Let us look into the positive sides of dating a widower, first…

1. Spends more quality time with you

Losing a spouse makes him value time more than anything. He will go out of his way to spend a good time with you and try to make the most out of the hours he spends with you.

2. Handles the relationship maturely

He puts into use all the lessons he learned from his previous marriage. This will work in your favor as your man will be more sensible towards conflicts or arguments.

3. Values your existence

A widowed man will always value your presence in his life. After his wife passed away, he found the love of his life back in you. So, you will be the most precious person to him in his life.

4. Shows more gratitude

A widowed man will be always grateful for the second time he got lucky with love. He will always be grateful for this relationship and will try everything to make it last this time.

5. Looks forward to the future with you

After his wife died, your man lived on with his broken dreams. Now that he has found you, you will be his hope in life. He will be enthusiastic to spend the rest of his life with you.

Inspite of all these upsides to dating a widower, it might not be very rosy for all. Some may get lucky while some might end up with the most complicated relationships of all.

Dating a widower can get seriously complicated as there are too many emotions – old and new at play. The downsides to dating a widower are…

6. Compares you to his late wife

It is of no use if your man keeps comparing you to his late wife. It will only create undue pressure on you for no reason. You are a different individual, and he must accept you as you are. It is a fruitless pursuit to try to compete with the memory of another person.

7. Might still be in love with his wife

It often happens that a man cannot cope with his loneliness after losing a spouse and jumps into dating to overcome that. But sadly, he might still be very much in love with his late wife. No matter what you do, you can never change it unless and until he wants to.

8. Refuses to acknowledge this relationship

If a widower has moved on with his life and is totally into you but still refuses to acknowledge the relationship; it might indicate that he is probably feeling guilty to have found a new love in you. Relationships with a guilty person never work out in the end.

9. Lives in the past trauma

If your man constantly brings up his wife’s death in every conversation you have with him, it probably means he is yet to recover from that trauma. It is only wise not to expect much from him and only enter a relationship with him after he recovers from the trauma.

10. He is confused

If your man jumps in and out of the relationship, it is a clear sign that he is still not sure whether he is ready to begin dating again. Dating such a man will lead to unnecessary chaos in your life, and the whole thing might just end up in heartbreak.

Dating a widow red flags

When things do not go as expected, even after you go beyond your limits, you make the relationship work; you must look out for the red flags. Look out for the bright red ones, and do not try to hide them in your closet. Act upon the signs immediately.

Let us read about the ten alarming signs you should look out for while dating a widower…

1. Hides the relationship

No one wants to be a secret lover. If you feel that your man is embarrassed by the relationship and wants to hide it from the public eye – that is a clear signal to end things right away.

As much as it hurts to say, this relationship will never see the day of light and will constantly make you feel like a mistress. If his intentions are genuine and wants a committed relationship, he will make efforts to introduce you to his family and friends.

2. Romanticises his trauma

It will be difficult to establish a successful relationship with a man who constantly wallows in his pain.

If he speaks too much about how hurt he is or how difficult it is for him to cope with the death of his wife; it means he finds guilty pleasure in it. More than a relationship, the man needs to see a therapist.

3. You remind him of his late wife

Widowers mostly look for a woman who might match the looks and personality of their dead wife. While it seems like a good idea, they are usually taken aback when reality hits them. No two people can be alike.

If you realize that he chose to date you over other women because you are quite like his late wife – get out of that relationship right away. It is a burden you do not want to carry!

4. He is still uncertain

If your man breaks up with you frequently and tries to get back again, it is a clear sign that he is confused. He wants to be with you but his guilt gets in the way. Do not carry on with such a man.

His doubt will slowly creep into you, and you will also feel guilty about your feelings. Leave the relationship and only get back with him once he is sure of what he wants.

5. He wants you to be like his late wife

There is nothing worse than to live in the shadow of a “ghost”. If your man constantly compares you to his late wife, be sure that he is still in love with her.

No matter what you do or how good you are in your aspect, you will never be enough for him. It is useless to try and impress someone who does not treat you like a match.

6. Makes you feel guilty

Widowers subconsciously criticize their new partners because they are used to certain things. If you cannot match up to those, he will most definitely point them out to you. That is harmless till the point he does not make you feel responsible for everything that goes wrong in his life.

If he sends you on frequent guilt trips, you might want to consider the option to part ways with him, or you might end up with mental health issues yourself.

7. Becomes too dependant

This is a warning sign most women ignore. They think that it is only natural for a person to be a little needy after a trauma like the death of his wife.

Watch out for signs like – always wants to be around you, needs your approval for everything, dislikes when you spend time with friends and colleagues, etc.

It’s okay to be a shoulder to cry on but make sure he does not get too emotionally dependent on you.

8. Refuses to create space for you

It is difficult to part with things with sentimental value. But it is also important to create space for the new.

If your partner hoards too much stuff from the past and refuses to make room for you, take that as a clear sign that he has not moved on yet.

He must be feeling insecure due to his past trauma. One cannot make room for a new relationship if your life is full of clutter from the past. It will be good to walk away from such a relationship.

9. You do not match up to his expectations

A widower might have bigger expectations from his next relationship. While he will put in more effort than the previous one, he will want you to match up to his expectations too.

You might do everything perfectly, but it will not be good enough for him. Talk about his expectations from the new relationship. If they do not mirror your expectations, do not carry on with the relationship.

10. Not ready to move on yet

Memories of past life will haunt a widower forever. But he must be willing to fight back. If you ever feel that the shadows of his previous relationship constantly jeopardize your equation with him, call it out.

If he does not mend his ways, he is not ready for a new relationship just yet. Spare your sanity and call it quits.

Dos and Don’ts of dating a widower

Dating a widower is perhaps the most complex of all relationships. You have to keep in mind that the rules of dating a widower are quite different from those of dating divorced or single men. It might look easy at the beginning, but you need to be cautious to make sure that things don’t go south.


So, let’s first begin with some things that will walk you closer to your dream man.

1. Handle with care

Dating a person with grief can be a challenge. Be kind and gentle in your approach. You should always watch what comes out of your mouth in the middle of an argument. One wrong comment can be detrimental to the relationship. Accept his fragile state of mind and behave maturely.

2. Be a good friend

A healthy relationship needs a strong foundation. Before anything else, you two must become good friends. You must become his lost support system.

Once he gets comfortable around you, he will not shy away from his feelings. It will be easier for him to take the relationship to the next level.

3. Give him time

Always be patient with him. Do not try to push him into a commitment. It will never be easy for him to share his space with a new person.

But since he is willing to date you, respect his situation and allow him the time and space to adjust with you. It may feel like an eternity, but you will reap the sweet fruits of your patience soon!

4. Listen more

When you listen more, you understand more. Let him speak his mind always. If he wants to share anything about his late wife, do not interrupt him.  

Rather, try to read between the lines and make sense of everything he says. When you listen more, he will feel more connected to you, and that is the basis of a strong relationship.

5. Be accommodating

Try not to be judgemental about his dating habits. Understand that your man was married before and so has been away from the dating world for quite some time.

This probably means his ways of wooing you might seem a bit old school. Instead of criticizing his dating habits, you should look beyond them – into the ingenuity of his intent.

6. Set your expectations right

It is very important that you both explain each other’s expectations from this relationship early on. Otherwise, it might end up in a mess for one or both.

For example, if you are into casual dating and you end up liking this man (a widower). But he wants a long-term or exclusive relationship.

Do not lead him on for months and leave him. It will only add to his pain and misery. Why be a cruel person? Be the nice lady and explain what you want from this relationship.

7. Build friendly rapport with his children (if any)

Suppose the man you are dating has children from his previous marriage. You must try to build a friendly connection with them.

You do not necessarily need to try to be the mother of his children, but if you build a healthy bond with them, it will add more strength to your relationship with the man.

8. Maintain your individuality

It is only human to be jealous and compete with one another. But in this situation, you will only end up hurting yourself.

Be confident in yourself and do not try to imitate his dead spouse or prove yourself better than her. He might not take it well, and you might come about as the desperate one!

9. Make him feel important

The mental and emotional trauma might make him feel small. Make sure you keep his spirits high and boost his confidence.

Always remind him of his worth in your life and how dear this relationship is to you! It will be easier for him to feel more connected and engaged in this new relationship.

10. Support him through his bad days

Even if a widower moves on with a new relationship, there will always be days when he grieves his past. Be sure to be there for him when he needs you the most. It will not be an everyday affair so do not be annoyed with him.

It takes a lot of time and patience to overcome grief. If he receives constant support from you, it will be easier for him to get out of the phase and dedicate himself to the new relationship with a happy heart.


There are a few things that are a complete no-no when you get into a relationship with a widower. If you are not watchful of these mistakes, the relationship may not go according to your expectations. Just be a little careful not to do the following things…

1. Ask too many questions

It is not a good idea to probe into his previous marriage for information about how his spouse died or how she was as a person. He might still be grieving the loss.

Too many questions related to his dead wife will be an insult to injury. Refrain from interrogation and be patient. He will open up about his life in due course of time.

2. Speak ill about his deceased spouse

Even if his late wife is not in this world anymore, he still might feel strongly about her memories. If it bothers you to hear about his previous wife, convey that to him politely.

Negative outbursts of emotions related to his previous spouse will make you look disrespectful towards him and his grief.

3. Feel insecure by the mention of the partner lost

If the man you are dating mentions his dead wife too often, do not feel insecure. Remain calm and deal with such conversations with maturity.

You should not be insecure about a person who exists only in his memory. You must understand that he will go down memory lane at times, but ultimately will return back to you only!

4. Expect emotional intimacy just yet

A widowed person’s emotions will always be in disarray. You must not expect him to sort out his emotions from the first day itself.

You need to work with him and help him through the process. Once he finds stability in the relationship, he will be able to feel more emotionally connected to you.

5. Compete to be better

Leave the jealousy and insecurities behind you before you start dating a widower.

It is natural to feel the urge to do better than his previous wife. But it will only create an unnecessary burden on you. A relationship is not a performance to put on.

Instead, focus on who you are when you are with him and what he likes about you as a person. Shift your attention to strengthen the bond that the two of you share.

6. Cut him short

It is rude and disrespectful to cut in between when someone else is speaking. This holds true for all relationships. But while dating a widower, you need to be a little more conscious in this regard.

Your partner might still be grieving the loss of his wife’s death. As such, he might often bring her up in the middle of conversations.

If you dislike it and keep interrupting him every time he speaks of her, he might just retreat into his shell and never open up to you at all. Needless to say, the relationship will gradually fade away.  

7. Force yourself into his life

Do not expect a widower to make you a part of his life from the time you two start dating. He needs to proceed at his own pace. 

Do not burden him with your expectations to get involved in his life too soon. He might not want it that way and prefer to stay away from you altogether.

8. Get impatient

Dating someone who is in grief needs a lot of empathy and, most of all, patience. Do not hurry him into a committed relationship too soon.

He will need time to lay his trust on you. If not, he might feel confused and go on a guilt trip over dating you. Either way, you will be the one who ends up hurt in the end.

9. Make him feel insecure

He has already lost someone dear to him and is emotionally vulnerable. Do not play childish games to make him jealous and win his heart.

He might feel apprehensive about the relationship and not put in enough effort to make it work between you two.

10. Play with his emotions

Be clear in your head about what you want from the world of dating – a casual relationship or a more serious companionship. Whatever it is, be sure to explain that to a widower before dating him.

After the loss of his wife, he may be looking for a lifelong partner again. In such a scenario, if you lead him on, only to end it when he gets serious, he will end up in more pain than before.

Tips for Dating a Widower

Dating a man who has tragically lost a partner requires oodles of sensitivity and maturity from your side. Not only must you be gentle when asking out a widower but you must also be prepared to accept their past along with your present feelings for each other.

We have compiled ten crucial tips to make life easier for you while dating a widower.

Read on…

1. Be mindful of the triggers

The death of a loved one leaves a scar on the mind forever. Emotional trauma is always accompanied by triggers (music, smells, thoughts, places, etc.) that might make a person recall that traumatic experience over and over again. Watch out for the signs.  

Always try to avoid doing or saying something that might trigger emotional trauma for him, especially if the loss of his partner is recent.

2. Be his constant encouragement

Emotional trauma and grief rob people of their confidence and strength. If you are dating a man who is grieving the loss of a spouse, be sure to encourage him all the time.

Societal pressure might make him feel guilty for stepping into the world of dating again, but it assures him that it is his fundamental right to a happy life.

It is not a crime to look for a new partner after losing one to death. Remind your man that he also needs companionship and love in his life.

3. Be the breath of fresh air

It will take your man some time to finally give up on the misery and embrace happiness. But in the meantime, encourage your partner to go out with you and do a fun activity once in a while.

For example, plan a short trip to a nearby town together or take up a random hobby together. It doesn’t need to be too adventurous. But something to take his mind off of the situation and more involved with you.

4. Engage in meaningful conversations

Communication plays a key role in building a strong relationship. If your partner is a widower, communication becomes even more important.

Talk to your partner about everything – your likes, dislikes, inhibitions, weaknesses, and most of all, about your feelings for him. You must also be receptive to his feelings and thoughts.

The more he opens up to you, it will be easier for you to be an understanding partner for him. Be his confidante! 

5. Bring his kids along

It will be an added brownie point for you if you get along well with his children. So once in a while, set aside a few days for an outing along with his kids.

Your partner and you can together accompany his children for an activity they would enjoy – like, a visit to the zoo, or to the amusement park, or even a sports meet, maybe.

You all can go on a short trip together. It will not only build a connection between you all, your partner will fall in love with you more!

6. Be respectful

Always be respectful while dealing with his children and speaking of his late wife. Your partner will never tolerate your impatience or rude behavior towards his kids. So be very cautious in this regard. 

Similarly, never speak ill of his deceased wife. Never criticize

anything related to his late wife. Not only will that hurt him, but he will

also feel that you are utterly disrespectful towards his family and feelings.

7. Keep your emotional baggage away

As it is, widowers are burdened by their own weight of emotional turmoil. Do not treat your partner like an outlet to vent out. Try to resolve your own emotional issues by yourself and only share if absolutely necessary.

Always remember – in the initial stage of dating a widower, you need to be the rock yourself to provide a solid foundation for the relationship. You need to be emotionally stable if you want to date a widower. 

8. Engage him in your life

Make sure he has at least a 50% (if not more) involvement in your life.

Ask for his opinion, introduce him to your friends and family, and invite him to parties with you- so that he can get a taste of what your life looks like from the inside.

It will help him to connect with you better on an intellectual level.

9. Make him feel protected 

You have to be his guardian angel. At least during the first few months of dating. He must know where to find solace when things get difficult. Hold his hands and guide him through the days when everything seems to go wrong for him.

Make him understand that even if the whole world is against him, you will stand by him and support him always!

10. Respect his choices

Discuss openly what he wants from you and how he wants to go ahead with the relationship. Respect his boundaries and never ask him to change if something doesn’t match your preference.

If you ever think that you would not be able to adjust to his choices, be mature enough to walk away instead of fighting and criticizing him later on.

How do you know if the widower is to date?

There will always be a few tell-tale signs which make it easier to understand if a widower is ready to get back into the dating scene. Still not sure what they are? Do not worry, we have got your back.

Here are the most obvious signs to tell if a widower is ready to date or not…

  • The most obvious sign to look out for is whether his actions mirror his feelings. It should not be like he says he wants to go out with you but instead keeps stalling you everytime you two plan a date together.
  • If a widower is ready for a new relationship, he will not be afraid to discuss the future of the relationship with his new partner.
  • Look out for signs that make it obvious that he is comfortable around you. For example, he behaves naturally and isn’t too conscious about his widower image in front of you.
  • He is willing to try new things with you and create happy memories together.
  • He makes you feel like the most important person in his life. He goes out of his way to impress you and win your heart.
  • If this relationship is not a rebound for him, he will not rush you to get physically intimate with you too quickly. Instead, he will take things slow to build a healthy mental bond with you first.
  • He values your presence in his life and respects the time you spend with him.
  •  If he’s ready to enter a new relationship, he will never use you as a crutch to help him deal with his past trauma. He will be able to handle his emotions well.
  • He will not shy away from his feelings for you or feel guilty about dating you. He will explicitly say that he wants to be with you.
  • He introduces you to his friends and family as soon as you formally enter into a relationship. He is not embarrassed about dating after his spouse’s death.


Now that you know most things about dating a widower, let me help you answer a few more commonly asked questions… so that you can move ahead with all the confidence in the world.

1. My boyfriend still keeps old photos and belongings of his late wife. Should I be concerned? Should I ask him to put them away?

It is one of the most commonly asked questions when it comes to dating a widower. While holding on to old photos and belongings might look like they have not really moved on from the old relationship yet. But honestly, there is no reason to worry.

It is a human thing to keep on loving someone even after they are no more in this world. The photos and belongings remain as sweet reminders of the love that once existed. It does not necessarily mean that they are still stuck in the past or are not ready for a new relationship. It can just be their way of honoring the deceased spouse.

Also, do not ask him to put the photos and belongings away. He might get offended. If the person is no more in this world, you do not have to feel insecure about his feelings for the deceased wife. She is a distant memory now and you are his present and future. Focus on that part!

2. My partner is still close to his deceased spouse’s family. Is that normal?

It is definitely not unnatural. Think about it. Your partner’s late wife’s family is a family to him too. Probably they have been very close from the start.

Just like you would not mind him staying close to his immediate family members, similarly, if your partner remains in touch with his late wife’s family, it should not bother you at all.

This especially holds true if your partner has children from his previous marriage. He might want his children to stay connected with their grandparents. In that case wouldn’t it be selfish and immature on your part to find faults if you want him to break all ties with his late wife’s family?

3. How can I get along well with my partner’s children from his previous marriage?

This is a wonderful way to strengthen the emotional bond with your partner. Before you jump into befriending his kids, you must discuss it with your partner.

Understand what his views are on the matter – whether he wants to introduce you to his children or wants to take it slow. Whatever it is, you both need to be on the same page when it comes to “his” kids.

If at all, he agrees to introduce you to his kids, make sure you have your stories straight and do not make up different stories about each other. If the children find room for suspicion, it will be very difficult to convince them to like you later on.

Also, make sure you do not force yourself into their lives. Do not try to be their mother but show interest in their lives. Win them over with kindness and love. Remember, just as your partner has lost his spouse, his children have lost a mother too, so be kind and gentle with them.

4. How can I support my partner through his difficult days?

There will always be days when your partner might feel more emotional than usual – on his late wife’s birthday, anniversaries, their children’s birthdays, etc.

It is obvious that these days are significantly important to your partner. If you want to be there for your partner to help him through those difficult days, speak to him directly.

Chances are high that he might want you by his side and expect you to support him through the emotional turbulence.

In that case, ask him if there is something specific he would want you to do for him. But do not get too obsessed and make it clear that you will have no issues if he wants a little time to himself on that day.

A word from ThePleasantRelationship

When you are dating a widower, it can be hard to interpret the signals, and a serious commitment might be too much to ask for at the start. Taking it slow is the key!

Dating them also requires patience and a willingness to embrace reality. Always be mindful of the fact that their loss will always find presence in their life.

No matter who you choose to date, the bottom line remains – If you are lucky enough to find a man who makes you feel safe, protected, and loved – treasure them. Even if he is a widower!

All said and done, the next time you come across a widower on an online dating website and you like him, make sure to swipe right with confidence.