Dating a widower

Dating A Widower: Dos, Don’ts & More

Last Updated on January 24, 2023

Dating a widower comes with unique challenges that you won’t come across when dating single men or divorcees.

At first, it may seem like a straightforward, simple situation. He is single, and understands what it is like to be in a committed relationship, and his experiences have probably made him a more sensitive and warm person.

However, apart from the benefits, you also need to be aware of certain red flags. Dating a widower and being romantically involved with them means that you need to brace yourself for feeling second best. This in itself can be very challenging, because you need to understand that you can never be their number one.

The chances of you finding a widower on a dating site are pretty high. Statistics show that 61% of men start seeking a new relationship after 25 months after their wife’s death.

So if you hit it off with a widower, how do you make sure things go smoothly?

To make sure things don’t go south, you need to be aware that the rules for dating a widower are very different. If you do not follow them, things can go very badly for both you and him.


The Do’s and Don’ts of Dating a Widower

Dating a man who has lost his long-term partner or spouse can be a very unusual situation for any woman. The biggest concern is that he may not have moved on from his deceased spouse, so you may question whether he will be able to give you the love you deserve.

The most difficult part of dating a widower is feeling second best. Even though you are in a romantic relationship with him, you might feel that the special place in his heart and life is already taken. If you really like him and the feeling is mutual, then don’t let such stereotypical thoughts stop you from having a relationship with him.

Let’s be honest, nothing is impossible and every relationship is different. But there are some rules that you can follow that will prevent you from feeling insecure when dating a widower.

Let’s explore some of the do’s and don’ts of dating a widower.

Do not be invasive.

The most important rule when starting a relationship that has the potential to flourish is to not ask too many questions about his late wife. You should avoid bringing up this subject on the first few dates.

First, get to know him better and allow him to open up about his past life. Don’t get too personal, too quickly. If you start attacking him with questions from day one, he may seem like an emotionally unavailable widower. Do not try to find out things that he is not ready to open up about yet.

Bear in mind that grief is not linear; it takes its own course. He could be grieving his deceased wife and, at the same time, looking to make new connections.

You need to be patient because building emotional intimacy with a widower does not happen overnight. It can take a lot of time before you get to this level with him.

Be prepared to listen.

Even if you don’t ask too many questions, you must be open to listening to his former spouse. The key to winning a widower’s heart is showing that you are open to hearing stories about his previous life.

He may have shared a beautiful marriage with his late wife and is struggling to get over her. If he is willing to open up about it, encourage him. You need to let him know that you understand and accept that his former spouse will always be a part of his life.

Do not let the whole “dating a widower feeling second best” mindset affect you when he fondly talks about his deceased wife. Avoid making him feel like you are competing with his dead wife for his affection and attention, as this is what pushes widowers away. If you truly like him, don’t let your insecurities get the better of you.

Understand that you will be competing with your memory.

The kind of relationship he shared with his wife will determine just how hard it will be for him to get over her and move on.

If he recently lost his wife, her presence might still be very strong and cast a shadow on your new relationship. Expectations lead to disappointment, so do not expect him to fall head over heels in love with you soon.

Rather, become a supportive friend in his journey as he works through and deals with his grief. Doing this will also help you form a deep, meaningful relationship with your new partner.

But, at the same time, protect yourself. Do not ignore red flags when dating a widower.

If all he ever does is talk about his deceased spouse and sulk, then take this as a warning sign that he is very far from getting over his dead wife. He might be looking to date only to distract him from the pain, which is not what you deserve.

Take it step by step.

Dating a widower is nothing like dating a bachelor or divorcee. The process is much more complex and needs time.

You may find it easy to date him, but much more difficult to commit to the relationship. Keep in mind that you could be dating a widower who is not ready for a serious relationship yet.

Take it one step at a time and give him space. This allows the relationship to grow organically.

We advise that you take it step by step. If you are interested in an unemotionally available widower, then you may need to put in even more effort for the relationship to work. It is important that you remain patient in the relationship and allow things to move at a comfortable pace for him.

Build a strong foundation now to prevent relationship problems with a widower later down the line. If you both genuinely care for one another, then be willing to take things at a slow pace.

Understand his traumatic experience.

Losing a loved one can be very traumatic. In cases where the death was caused by unnatural elements, the pain is usually deeper.

Think about how difficult it is to forget someone you truly loved because of a divorce or breakup. When it comes to the death of a spouse, grieving is much more painful.

In these situations, even the slightest of triggers can bring back heartbreaking memories. It is important to be thoughtful of this to be able to empathize and understand the behavior of a widower.

When you are dating a widower, do not take offense when you get emotional reactions to small triggers. These are not warning signs telling you to end the relationship. It is just part of the grieving process that will ease or become more manageable in time.

You should not be at the receiving end of his guilt.

Understanding pain is one thing, but you cannot be with a widower who refuses to move on. Similar to how a breakup only hits men later, the sorrow around losing a spouse can have the same effect.

The widower may have entered the dating scene, but if he unintentionally compares you with his late wife or continuously talks about her death, then this may be a warning sign. A red flag signals to you that you are dating a widower who is subconsciously guilty.

You will need to make the difficult decision of how long you want to date a man who lives in his past. Dating a widower who is not prepared to move on can be pointless.

You need to think carefully about whether it is worth your time to emotionally invest in him. It is impossible to develop emotional intimacy with a widower and expect a successful relationship if he is not willing to open up to you.

Don’t be judgmental about his dating pattern.

Dating coach, Apollonia Ponti, highlights that there is no right or wrong time frame for a widower who has lost his spouse to start dating. The grieving process for each person is so different. So avoid judging a widower when he begins dating after his wife’s death.

Certain people prepare for the worst and grieve less, whereas others may look for a new relationship to fill the hole in their hearts.

Generally, men feel very lonely after a divorce or the death of their wife. So when dating a widower, you might as well leave your judgment at the door. Enter the new relationship with an open mind so that you can accept him for who he is.

Communication is key.

Be sure to always express your feelings. Even though it may take a long time between getting to know him and being in a committed, serious relationship with him,

You need to make sure that there is open communication at all times. Especially if you’re insecure or worried that he won’t be able to love you as much as he loved his deceased wife.

Talk about things to get more clarity on the extent of his feelings for his late wife and his feelings for you. This is essential if you are with an emotionally detached widower and you are both looking for a stable, long-lasting relationship.

When a widower starts distancing themselves, do not just let the whole relationship dissolve. Have an open and honest conversation about what you both are seeking from this relationship.

Communication is significant in solving problems in any relationship, including your relationship with a widower. Work on creating honest and open communication channels in your relationship. This will help strengthen your bond.

Win over his children

You know a widower is serious about you when he is ready to introduce his children to you. If you genuinely love him, make an effort to befriend and bond with his children.

If marriage is on the cards, then you definitely have to work on the relationship with your future stepchildren. But this can be a very delicate situation that needs to be handled with care.

You need to prepare yourself for hostility and openness because the situation could go either way. Despite the situation, you have a chance to get closer to your partner by showing him that you are willing to befriend his children.

Whatever you do, make sure you never imply that you are here to take their mother’s place. This could backfire and cause some serious damage to your relationship.

You and your partner need to be on the same page about what the children know and how you will be introduced. Your decision may depend on the age of the children and whether you are the first person the widower has dated and his kids have met.

Minor children usually test adults to make sure that their stories match. That is why it is important to be on the same page in terms of information and language.

When you meet the children, take their lead. If you have the chance to show an interest in learning about the deceased loved one, then ask questions. But do not force it.

Remember, their deceased mother is still very much part of their family. You are not there to replace her, but to fill a new space in the family. The more you show the children that you understand this, the better the situation will be.

Handle his ex-in-laws with caution.

It is one thing for him to handle his children, but if their family was very close, then the chances of him still being in touch with his late wife’s family are very high. Losing strong connections with his late partner’s family may feel like another loss to him.

The relationship he still shares with his former in-laws might be an element of comfort for him. He may treasure the love and support of the family, as they are the only people he can share his memories with. But their equation with you may not be the same.

If you are uncomfortable, you may decide to keep yourself away from his extended family. Unless they are openly hostile towards you, try to have a positive association with them before you decide to give up.

It is completely normal to feel insecure about dating a widower who still behaves with his deceased spouse’s family as if they were his own. You may feel like an outsider and think twice about where you fit in his life.

But, if he is taking the initiative to introduce you to his late wife’s family, that is a great sign. It shows that he is ready to welcome you into his life and wants you to be part of his close inner circle.

Don’t be afraid to ask for his advice.

If both of you are looking to take your relationship forward, don’t hesitate to ask for his advice on being accepted by his children and family.

Regardless of his own experience, it is his duty as your partner to help you become more comfortable with his kids and family members. Don’t do this alone; work on it together with sensitivity and compassion.

One of the major relationship issues when dating a widower is gaining trust and being accepted by his children and family. Your partner needs to have your back throughout this process.

Understand what he wants.

Happy Couple

According to Apollonia Ponti, the best thing about dating a widower is that they know exactly what they want. Someone who has experienced the death of a loved one is generally very clear about their relationship needs. They may look for new things or want a similar love story.

Figuring out how to date a widower can be determined by what the person you are with is seeking. They may have shared a very intense connection with their late wife, and are looking for companionship.

Widowers who are looking for companionship should seek a woman who will fill the hole in their hearts. They believe that having someone in their lives will help heal their hearts and remove loneliness. Sometimes their strong desire for companionship makes them jump into a serious relationship and date a woman they wouldn’t ordinarily have a relationship.

Avoid high expectations.

If you start a relationship with an older widower, who has lost his spouse after years of marriage, he may have very different expectations from yours. You may have shared common interests, but forming a new relationship may be difficult for him.

His grief may hinder your relationship, preventing him from creating a deep, meaningful connection with you. Maybe he is in a phase in life where love and relationships mean something different to him than to you.

Be realistic about your expectations. This is even more important if there is a big age gap between the two of you.

Don’t try to take his ex’s place.

The worst thing you could possibly do in your relationship with a widower is to try and fill her late wife’s place by changing your personality to match hers.

When you are dating a widower, make sure that they are not looking for someone to fill a void in their life. Nobody can fill the void left by the loss of a loved one. You can show empathy, but never stop being your own person.

That being said, you cannot expect his previous wife’s memories to vanish overnight and for him to begin a new life with you while pretending she never existed. You need to understand that there is enough space for both of you in his heart.

You may find that certain parts of his life and personality will always be associated with his late wife. Some of these may include his children, his beliefs and values, and his lifestyle.

You need to accept this and learn to create something new with him around these things, without trying to overshadow them.

Do not badmouth his former spouse.

Dating a widower is not straightforward. It can be very difficult at times. You may find yourself getting irritated every time you are unintentionally compared to your deceased spouse.

He may reflect on the past more than you’d like. But even during those moments, never make the mistake of talking badly about your late wife. No matter how bad an argument gets, do not bring this topic up, as it will only add fuel to the fire.

These are the situations that cause a widower to distance themselves. The best way to avoid this is to stop competing with someone who is no longer alive. Rather, focus on your relationship’s present and future.

Dating a widower is so much easier when you are not judging him for his past.

Be prepared for intimacy problems.

Physical and emotional intimacy can be an issue in the beginning, but this depends on the nature of his previous relationship and the time frame since his wife died.

If a widower has come to terms with his grief and is open to a new relationship, then you may not experience these intimacy issues. But if he is still grieving, he may find it hard to emotionally connect with another woman.

Do not judge him. Give him some time or discuss your concerns about intimacy. But if these intimacy problems continue, encourage him to get advice from a professional. Depending on the extent of the disconnection, he should get in touch with a sexologist or therapist.

You will need to put in a lot of effort and patience when developing intimacy with a widower. It is important that he meets you halfway and puts in just as much effort, otherwise, it’s not going to work.

Watch out for the red flags.

A red flag that you should not overlook is when a widower distances himself from you the moment you mention getting serious in the relationship.

Watch out if he hesitates to introduce you to his children, family, and friends. This will lead to an unhealthy and unstable relationship.

Another red flag is that you may remind the widower of his late wife. Sometimes widowers want a woman who resembles and acts similarly to their deceased spouse, which isn’t a warning sign. What you should be worried about is if the widower tries to mold you and the relationship into the one he shared with his former spouse.

Here are some signs that he is trying to replicate your relationship with his previous one:

  • He will verbally compare you to his late wife through vague hints.
  • He always highlights the physical characteristics that you share with his deceased wife.
  • On a date, he asks you to put on his former wife’s clothing and behave like her.
  • He takes you to the places he went to with his deceased spouse, like restaurants and holiday destinations, and refuses to experience new things with you.

These warning signs show that one) he is not committed to you the way you would like him to be, or two) he has not moved on from his previous marriage. It is up to you to make the call on how long you are willing to wait before he musters up the courage to make your relationship official.

Do not ignore these red flags for dating a widower, because they will come back and cause you more pain later on in life. Recognize and accept the difficulties that may arise while dating a widower. Think about how to manage them, but always keep your best interests at heart.

Don’t let photos make you insecure.

A guy showing photos to his partner

A common problem encountered by women who are dating widowers is how to behave when their partner refuses to get rid of his late wife’s presence. This could be photos or even memorabilia in the house.

You should not be asking them to remove these items in the first place, as this could threaten your relationship.

It is completely okay and normal for a widower to display pictures of their deceased spouse, especially if they have children who live in or visit the home.

Photos do not mean that someone is stuck or not ready to move on. It just means they continue to love their deceased loved one while at the same time making room for new things in their life. You are a new aspect in their lives, but this does not mean you are replacing their late wife.

Give him space.

Every relationship has its own issues, but when it comes to dating a widower, you are faced with unique challenges.

Significant dates may be very sensitive and painful, such as their wedding date, his late wife’s birthday, their wedding anniversary, her death anniversary, and their children’s birthdays. Remember these dates and give him space to grieve.

Express your agreement with his feelings. Be understanding and open-hearted. Giving him space when he needs it the most can be a lovely gesture. But be there for him when he wants to open up his heart.

Never see his emotional investment in his past as a threat to your relationship with him. Just because he has you to start a new life with, does not mean he can erase his past.

Communicate your relationship goals.

If you fall in love with a widower and share a serious relationship with them, but are still unsure of your place in their life, don’t be afraid to ask them questions that will give you clarity on your status.

You need to have a discussion about certain things with your partner. According to relationship coach and author, Abel Keogh, there are three basic questions you need to ask:

  • Do you love me?
  • Do we share an exclusive relationship?
  • Where is this relationship heading?

The responses will help you decide whether or not to continue the relationship.

Of course, dating a widower is different from every other relationship, but it is still important for both of you to be on the same page. You need to know where the relationship is going and what to expect in the future.

Create new experiences

The best way to erase feelings of insecurity when dating a widower is to create new memories with your significant other. He may miss his late wife during celebrations like birthdays or festivals.

Never compete with his deceased spouse, but make life more fun by doing things he enjoys with your special touch. Make sure holidays and special occasions do not resurface painful memories, but rather create new ones for your relationship.

Five signs a widower is serious about your relationship:

Dating a widower can be emotionally draining, especially if you are not prepared for what could happen. Before you invest your time and heart in him, make sure you are both on the same page and have the same goals.

Abel Keogh shares five signs that indicate whether the widower is ready for a serious commitment.

1. He does not hesitate to introduce you to his children, family, and friends.

A widower who has entered the dating game and is not afraid to let his family and friends know about you shows he is ready for commitment. You won’t be cut out of family activities because of excuses like “they can’t see me with someone else yet” or “they are still mourning”.

He won’t be affected by what other people think of him dating again. All he cares about is whether you are happy. But if he prioritizes others’ needs, then he is not ready.

A widower who is happy for you to be by his side and wants the world to know about your relationship shows that he is serious.

2. He does not pressurize you to get into bed with him.

It can be challenging to get physically intimate with a widower, especially if you don’t know where you stand with him. Does he only want to sleep with you because he misses getting physical with his late wife?

If you are not prepared to jump into bed with him, you need to keep your ground and say “no.”

A widower who respects you and the relationship will not force you to sleep with him. He won’t mind waiting until you are comfortable taking the relationship to a physically intimate level.

And after you say “no,” he won’t constantly pressurize you or sulk that you are not sleeping with him.

3. He wants to talk about where the relationship is going.

Men generally don’t talk about what the future of a relationship holds. But when they meet their person, they will be willing to talk about dating exclusively, getting engaged, and marriage.

The same applies to widowers. If he believes that your relationship has potential, he will talk to you about it. However, if he avoids the topic and says that “it is too soon, he needs more time” or that he is “still mourning,” then this may be a warning sign that he is not prepared for a serious, committed relationship.

4. He won’t let his grief work become an obstacle.

When the right person enters their life, some widowers will do anything to get over their grief. They might get rid of the shrines of their late partner and even sell their houses.

He’s not going to make excuses for why the relationship can’t move forward. Instead, he will make an effort to put his deceased spouse aside and make you the center of his attention.

But if he constantly tells you that he is still mourning, then he is not ready for a serious relationship. You need to end the relationship and find someone who will treat you the way you deserve.

5. His actions speak louder than his words.

Have you ever heard that “action is louder than words”? This phrase is also important when it comes to widowers. Anyone can say something, but you need to see whether their actions match their words.

If he talks about how much he loves you but treats you terribly, then you know he is not serious about you or the relationship. Don’t put up with bad behavior or settle for less than you deserve.

If he truly loves you, he will show you.

Frequently Asked Questions

Why is dating a widower so difficult?

Dating a widower is challenging because each person has a different grieving process. Losing a loved one is a very traumatic experience and brings on a lot of pain. For these reasons, a widower finds it hard to open up or commit to a new connection.

How do you know if a widower loves you?

Couple sitting in a restaurant

A few ways you can tell if a widower loves you are: if he does not compare you to his late partner, he is ready to make your relationship exclusive, and he wants to introduce you to his children, friends, and family.

Can widowers ever move on?

Yes, widowers can move on, but this depends on the nature of their previous relationship and the time since their wife died.

What should I expect when dating a widower?

When dating a widower, you need to understand that you will never be able to erase the memories of his late partner. You may even find yourself competing for attention if he brings her up often.

Final thoughts

Losing a partner can be a life-changing experience. When you are dating a widower, you need to be mindful of their loss and respect the changes they are going through. But you also need to respect yourself. Be aware of the red flags and do not just settle for anything.

John Santana

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