Dating a Widower? Hear What Women Have To Say About It


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By Jackie Pilossoph, Divorced Girl Smiling Editor-in-Chief

I personally have never dated a man whose wife died, but I know plenty of women who have. From what they tell me, dating a widower isn’t easy. Then again, neither is dating a divorced man. What are the differences? What are the challenges of dating a widower? And are there positives?


I decided to sit down with a group of women, all who have dated a widower, and ask them about their experiences. Here are the highlights of the discussion:


  • 1. How is dating a widower different than dating a divorced man?

In any other situation, finding a mate is all happiness, but with a widower, it can be tempered w guilt. Widowers feel guilty that they are still able to enjoy happiness, while the person they lost can’t. They might also feel worried about other people’s perceptions. In other words, maybe others will judge them for finding happiness again. They might think, ‘Does being happy make people think I didn’t love my spouse?’


  • 2. What are some challenges you have faced?

There are both physical and emotional challenges. Physical reminders–mementos, personal effects, wedding pictures are difficult to see around the house. And it’s hard to determine the right time to speak up. You don’t want to sound insensitive, but you him to start letting go of the past and embracing the future. That’s not easy to do if his late wife’s clothes are still hanging in her closet. Emotional challenges involve certain days of the year, like the day she died or her birthday. Also, holidays that should be joyful (like Christmas) sometimes serve as sad reminders to the guy, when all we want is to celebrate like everyone else does.


  • 3. What helps in having a successful relationship with a widower?

Communication is so important. You can’t assume you know what they are feeling. You have to have patience, but still be firm in letting him know what you want and need to be happy. It’s easy to fall into the trap of catering to their widow status rather than making sure your emotional needs are being met.


  • 4. Any tips for someone dating a widower?

Don’t’ make demands but make sure he knows what you need. Keep in mind that everyone has catered to him for a long time, and that could possibly cause him to be a little bit selfish. Not that it’s his fault, but he might forget how to date properly and might not make the effort. The widower needs to learn how to be sensitive to you, as you are to him. Also, don’t let insecurities build up about the past. Raise the issues as they come up.

5. Is dating a widower ever hurtful at times?

It is hurtful to wonder if he will ever love u as much as his late wife, if you’ll ever be the most important person to him, if his loved ones are comparing you. Its hurtful to see that his identity is based on being her husband and you wonder if he can create a new identity. Its hurtful to feel like you can’t experience a holiday without it triggering memories of her.


6. Anything you want to say to a widower who might be reading this?

 No reasonable person expects you to forget your spouse. Dating someone new is about finding balance. It’s about taking the 8 by 10 wedding photo in the foyer down, knowing that your new girlfriend has no issue with you looking at photos of your wife whenever you want. We feel like if we say anything about taking the physical mementos out of site, you (the widower) automatically hears “shred everything” and that’s not what we’re saying. It just means put them in a more private place.

  • 7. The bottom line?

It’s important to apply the same standards to a widower as you would to any other guy. The only difference is you might need to have more patience. Having standards doesn’t mean you aren’t empathetic to the pain he’s gone through. Don’t settle for less from him than you would for any other guy.
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Author: Jackie Pilossoph

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29 Responses to “Dating a Widower? Hear What Women Have To Say About It”

  1. Mary Beth Alger

    The best advice I’ve read. I am totally in love with a widower and it’s bloody not easy!

  2. Jackie

    it’s so nice to hear ‘you need to make your needs felt’ instead of ‘oh but he’s still grieving’.
    & as Mary Beth says, I love my widower to bits but it’s HARD…..& I’m a widow!!

  3. Michael

    It’s the widower that needs to be careful. If our marriage was a good one, we have a lot of love that we carry in our hearts. I loved being married and transferred that love to an undeserving woman. She was using me to build her self-esteem after being abandoned by her husband of 30+ years. Divorces don’t usually leave women in a good state of mind. From now on, no more women whose husband’s have left them. Men do not walk out on good women. Unfortunately, I have given up on ever meeting anyone and am currently liquidateing assets so that I can use my “unattached” status to travel the world.

    • Jackie Pilossoph

      I find the statement “men do not walk out on good women” extremely offensive. And actually, my husband did not leave me. But, i know countless amazing women–beautiful physically and smart and driven and kind, whose husbands left them. ARe they damaged? Certainly in a way. But many of them go on to meet men and fall in love. Everyone–men and women have baggage after divorce or after a spouse dies. or, even people as they get older. But if you look at it from a positive angle, that’s what makes people interesting and real and vulnerable. Men certainly do walk out on good women, and women walk out on good men, too.

  4. Marie

    I know this is a old thread. But here goes. I reconnected with my first love. We are both 50. His wife passed away 3 yrs ago. They was together 25 yrs married 10. He is a alcoholic. They both was drinkers but he is so bad. Starts drinking 10 am takes a nap and continues till evening. Our sex life is getting better but he is addicted to porn. All he talks about is her. It drives me crazy. I live with him her pictures are everywhere. He compares me to her tells me how hot she was. Thin. And short ( I am only 1 1/2 taller then she was and I am not heavy at all. I have constant depression and anxiety. I have dated divorced men and that was so much easier

  5. Anonymous

    I’ve been dating a widower a year and a half now ,
    We got together 7 months after he lost his wife that he really loved
    He told me from the beginning he wasn’t ready to get in a relationship till I appeared he said if I canhave patience or if I can’t help understand
    I stayed he would disappear not answer messages or my calls but I was there when he would get out of his cave, sometimes a week sometimes over a month
    He wouldcome back was if we were together the day before ( I felt the same)
    2months now we have spent heaps of time togetherI thought we were on a good level as he would tell me he wasn’t up to going out we got real close and suddenly I get a message saying I’ll be going in my cave for a week ( at least he let me know this time)
    & its been a month now that we don’t have any contact he wount answer my messages or calls
    What should i do?
    I know it’s not over because I’m sure he would have told me
    It hurts
    I’m in the dark
    Will he come round soon?

    • Jackie Pilossoph

      I’m so sorry you are going through this. Just try to realize that this is his issue. It has nothing to do with you. Is he getting help? counseling? I wish I had the answer–give him space or push? No idea. It’s a sad situation. I wish you both the best.

  6. Lou

    I met my widower 20 months ago on a dating site. i love him dearly and we have a very compatible day to day life together at his and his departed wife’s beautiful house . My ex marital home is currently for sale. He is kind, caring and we have everything in common but I am finding things increasingly difficult as It feels as if she is still here in the house, photos, purse, handbag, every trinket even if its dislike by him, absolutely everything is still in the drawers, boxes of photos under our bed, and a new one of the wedding 40 years ago recently put onto the window along with four others now in the dining room which looks into the kitchen.. if something has been misplaced…he assumes I have thrown something of hers away..I have been totally sensitive, loving, forgiving…everyday, even after nearly two years ago she is referred to as us and we and when I sat him down for “the honest chat” he said he loves the time we spend together but needs his space…yet if I’m away for a few extra days, he wants me back. I am in all sincerity a loving woman who has been hurt physically and mentally before but find this so difficult to ‘settle’ into the relationship and keep giving my all to it that I’m hurting inside. I’m a gardener so do his vast gardens in between my clients, clean, cook and behave like a wife. His daughter is sweet with me and shows no resentment despite being broken hearted over her mom, but I have to be silent and pretend I’m not around when he rings, his son never invites ‘us’ to his house only his dad nor have I met the grandchildren … it breaks my heart even tho I never criticise or raise the issues. I guess I’m heading for a long friendship if I accept the terms I’m offered. We have never been away together
    and I recently heard him quietly reply to an old friend who thinks we are wonderful couple, that ‘no…he likes his own space’… I guess that was would you ever marry her. Sometimes life can be sad and wasted from guilt. Such a waste of life ahead. I know he adores me, misses me but let’s face it..he can’t possibly love me.

  7. Mike

    I am a widower and I have been dating a widow for the past 3 months and find that we both have similar backgrounds and life experiences. We both had long term marriages for over 35 years. Both of our losses are under a year. We talked on a site and then exchanged numbers. We talked on the phone and then we met. We have discussed our spouses and it made things a lot better for each of us. If this was any other time I could say that she was “the one”. We go out weekly and make long term plans. We have both met members of each others families and are very comfortable together. One thing is we are taking things at a snails pace. We both have expressed that we “like” each other and talk and text daily too. What I guess I am trying to say is that we both are grieving and what makes this relationship special is that we respect each others wishes and understand what we both experienced. Mine was sudden, hers a long term situation. I feel that because of that our relationship will be on more solid ground and that we will grow together. When we met each other we both knew what we were doing but at the same time we both found the support of each other to go out and do things instead of locking ourselves away and wasting away. I am so glad that I wrote to her, and she to me. It has made our lives so much brighter! I just wanted to post my comment to let you know that patience and respect and understanding can make a world of difference in your life. Again I am a widower she a widow so maybe thats the key to our good match up.

  8. Mike

    When I said if this was any other time I would say that she was “the one” I failed to finish that thought. I meant that she is so perfect for me that had this been many years ago she would have been the one I married. That she is perfect for me right now. That she has captured my heart. Going out to “date” again has changed both of our lives. But we are taking things very slow so we can build on this and have that wonderful relationship we both desire. I just wanted to clarify that comment because it doesnt sound right as originally posted.

    • Claire_Dernel

      This is lovely to read… I have been dating a widower for a year now, we met 2 yrs after his wife passed away. I am divorced in very good terms for 3 yrs now, and we met each other in a dating website in 2015.
      It’s interesting because the first time I googled about dating a widower I read some crazy stories, almost all of them describing a relationship I wouldn’t feel comfortable to be in, and I couldn’t relate to it very much.
      Sometimes I have some insecurities, but I had some insecurities in past relationships too, so I guess this is quite normal.
      I developed a strange feeling towards his late wife… I like her, and I feel we would have been good friends. I got to the point I even had dreams of her being alive, and being so happy about it! Chatting with her when we have never actually met each other. I felt terrible in the morning when I woke up and realized it was a dream… and I got even worse when I realized he certainly has these dreams too and I can’t imagine the pain of waking up and being dragged to reality.
      Regarding my insecurities, I used to wonder if I am a reminder of his loss and he is with me because I am the closest person around who reminds him the relationship they had. In time, I realized that this is nonsense… not only because our relationship is different, but also because I am a completely different person and so is my boyfriend since Mary (late wife) passed away.
      Anyway, I am writing this because no relationship is a walk in the park and easy, but I think it is not supposed to be so difficult and full of pain.
      Unfortunately, life is full of unpredictable sad moments, and we should always be sensitive towards people’s feelings, but I don’t think this is a green card to put their feelings over ours all the time.
      I was married to a great guy but we didn’t work as a couple due to an illness he developed. He was married to a great woman but she passed away. Our past lives are not an option anymore, so we had no other option but accept reality and move forward. I can’t compare the processes we have been through, but the one thing I know is that we are both committed to this idea, and we expect nothing but making each other feel loved all the time, and I don’t think we should settle for anything less than this.

      • Jayne

        I’m so glad I found this sight. I’ve known my widower for 3 years now. When we met we were bothing going through a divorce. Both our spouses had an affair. A short time later we found out his soon to be ex had terminal cancer. I was by his side whenever he needed me. It was one of the hardest things either of us had ever dealt with. Uncharted waters. As tough as it is to deal with the rollercoaster ride I love him and feel our relationship is worth the work. Thank you everyone that has shared their experiences. It makes me feel there is hope. Every relationship has it’s challenges, these are just a little different.

  9. Kt

    I met my widower on a dating site. He has been widowed for 8 years. He says and does all the right things. But sometimes I feel a disconnect. I have met his family and his children. He has expressed he wants to marry me one day. He is making little changes around his home. He even bought me a toothbrush and bath towels for when I spend the night. We have not had sex, but we cuddle. Am I reading to must into this because of the disconnect. This is new territory for me. Help

  10. Kt

    I’m dating a widower. This is new to me. His wife died of cancer 8 years ago. I have met his family and his children. All like me. He has talked about marriage and spending the rest of his life with me. He is very accommodating. He takes my advice in his personal affairs. He has made room for me in his home. We have not had sex. All is well but every now and then he is very distant. Should I ask him about this or go with the flow. As I stated this is new to me

  11. Olaide

    Best advice anyone dating a widower could ask for … I’m currently dating a widower… he used to be my ex boyfriend but we went different way, I had a child but wasn’t married… he got married and had two children but lost his wife… I really don’t know but we found ourselves coming back and getting so use to each other .. it’s 7months now since he lost his wife but I know too well we are both in love… sometimes the thoughts of us being soul mates comes to me cause even though at some point we weren’t together , we still got way to communicate with each other when we could even know he wasn’t cheating on his late wife with me then.. could this be a green light? His kids love me, my son loves him and his kids.. his mom and siblings love me too. Any thoughts ?

    • Jackie Pilossoph

      I think this is great! Just don’t rush anything. Keep having fun and enjoying each other. the biggest mistake (in my opinion) that couples make is rushing into marriage. Just let it happen. So what if it takes a long time? Just enjoy every day. It sounds like it’s a great, great relationship. I”m happy for both of you!

  12. Diana

    I am a widow of 19 years and dating a gentleman widowed 7 years. There are times we do well and other time I am in limbo as to what to do or where I stand. I am old enough to not act foolish, but I really like this guy. I am willing to let time take its course, but there are times i get impatient. Such confusion.

    • Jayne

      You sound exactly how I feel. It’s so comforting to know there are other woman out there dealing with the same situation. I appreciate the good times and hold on tight during the tough ones. Giving him space to work through his feelings is probably the hardest thing. But he always comes back so I just hold onto that. Being patient isn’t always easy. I wish you the best.

  13. Melanie

    I have really enjoyed reading these tips and comments. I have a few questions myself. I have been dating a widower for almost 2 years now. He us 68 and I am 69. He was married to her for about 13 years. He said that a couple years into the marriage she told him he could go do whatever he wanted with whoever he wanted because she didn’t care. Yet he stayed with her. She has 2 children who are grown and have children of their own. He is close to them and their children. They call him grandpa, etc. I don’t have a problem with him staying close with them. However he keeps wanting me to go with him to visit them and I want nothing to do with it. I don’t like the idea of going to a place where I will have to see pictures of him and her together, etc. I haven’t said anything to him about this. I keep thinking it will cure itself. In some ways I think I am being small but then in other ways I feel that our lives together is going to be short as it is and I dont want to be spending it with her children. I would really appreciate any feedback.

  14. Melanie

    I have really enjoyed reading these tips and comments. I have a few questions myself. I have been dating a widower for almost 2 years now. He us 68 and I am 60. He was married to her for about 13 years. He said that a couple years into the marriage she told him he could go do whatever he wanted with whoever he wanted because she didn’t care. Yet he stayed with her. She has 2 children who are grown and have children of their own. He is close to them and their children. They call him grandpa, etc. I don’t have a problem with him staying close with them. However he keeps wanting me to go with him to visit them and I want nothing to do with it. I don’t like the idea of going to a place where I will have to see pictures of him and her together, etc. I haven’t said anything to him about this. I keep thinking it will cure itself. In some ways I think I am being small but then in other ways I feel that our lives together is going to be short as it is and I dont want to be spending it with her children. I would really appreciate any feedback.

  15. Nancy

    I am at a loss! I have close friends I have known for 23 yrs. Since meeting them there has always been this…connection between him and I. Nothing ever happened as we were both married. My girlfriend (his wife) was diagnosed, battled cancer for 2 yrs and passed away August 2016. For 3 months after her passed he pursued me, wanting to date. Him 52, me 47…I was very hestiant as I questioned whether he was ready and was worried that if it didn’t work out I didn’t want to loose him as a friend. We talked about this repeatedly and he kept assuring me he felt ready and that knowing my past history (my ex cheated on me) would never hurt me. We dated for 7months, there was quilt as he felt like he was cheating on his LW and that he was happy and I felt like I was betraying my friend. We talked about it but felt that our relationship felt right! He was told by a friend of his LW that she often spoke of me with her friends and even told one of them that she thought him and I would get together. We felt it was meant to be. After 7months on July 25, due to his job he saw a Psychologist. I don’t know what was said but I do know that since 18yrs old he has never been alone. He has been dealing with anger issues, and he’s not an angry man. I told him it was is grief has the 1 yr anniversary of his LW passing was in a few months. During this time on a couple of occasions his angry bubbled over and he snapped at me, immediately apolozing and feeling horrible. It wasn’t right and I didn’t deserve it but I understood were it was coming from. After the time with the Psychologist he realized that he hasn’t finished grieving for his LW and that he isn’t ready for a relationship. He broke up with me saying he needs time and space. Of course we are both devastated as we were talking about a future together with me and my 2 boys and buying a house and vacations…etc. I know he would never intentionally hurt me and that he didn’t see this coming just as much as neither of us expected these feelings. I have been trying to give him the space and time that he asked for but it is extremely hard. He has been texting me occasionally and calling me. This has absolutely destroyed me! In the past 5 yrs I have had so much go on in my life that him breaking up with me has made my “cup” over flow and I can’t seem to pull myself up. It has been 2 months and I have my good days but most are bad, I am off work on stress leave and seeing a counsellor. I know in my heart that he is having a hard time with this and I hadn’t told him how truly hard this has been trying to stay strong for him but I don’t want to lie and feel it’s important to keep the lines of communication open and honest. I feel him distant and holding back his feelings and having to do this to help him get through this. A week ago we spoke on the phone for an hour it was raw, open and honest. He said he has a hole in his heart that somedays he feels it would just be easier to jump in front of a bus, that he thinks of me the minute he wakes up, all day long and when he goes to bed. I told him everything I have been going through and that I haven’t been able to work, crying everyday, feeling empty and all that he is feeling. He is embarrassed that his angry bubbled up at me and again I told him I understood but he says I’m validating it. No, it wasn’t ok and I do deserve better but I also know that that isn’t him and if he wasn’t working himself to exhaustion and dealing with grief of his LW and know grief of pushing me away it would never have happen. He admitted that he is running away. He needs time to find himself and learn who he is. I asked him to please not run away from me I understand that need to find himself but I could bare not having him in my life. At the end of our conversation I asked if he was ok with me still telling him I love him and before I could finish he said “You have no idea I Love you so, so, so much ND!” I know he loves me and that this is tearing him apart. Except for a couple of texts Monday and an apology for not calling (like I said he is working himself to exhaustion during the day his reno/ carpet business and evening paramedic) I haven’t heard from him and it’s killing me. I love this man with all my heart and know, understand and respect he needs time but this is so hard my heart hurts and I don’t know what to do!!!

    • Lynette

      WOW! Your situation sounds exactly like mine, except it was not a friend.

      I started dating a widower around October 2017 and it had been over two years since his wife passed away. We met online, he pursued me like crazy. I’ve never been married but have an adult child and he was married twice, his late wife being his second marriage. He has 3 kids, but none with the late wife. Everything was going great, it was the most intense relationship I’ve ever been in. It was long distance, but we met every month and spoke on the phone, FaceTimed, texted, email everyday. He spoke of marrying me one day. He came to my hometown to meet my family. I was scheduled to meet his family (not including his daughters and he did not meet my son) the week of Christmas 2017. One week before I was scheduled to fly into town, he canceled my visit, told me he was depressed because of the holidays. He brought up his late wife and her daughter saying how much he misses them both. He is still close to her daughter and her family. I was patient with him and understood he was still grieving. He talked about his late wife every day in our general conversation and even had picture of them saved on his phone as his screen saver so I had to see this every time he opened his phone. I never said anything to him about it.

      Once he canceled my visit, he told me he needed “more time” to himself. I gave him that. I didnt speak to him or call him for two weeks to give him time to collect his thoughts. He was also seeing a therapist. Then on New Years Day 2018, I called to checked on him and found out he blocked my number. However, he did not block me from contacting him on social media or WhatsAPP. This really hurt my feelings because I did absolutely nothing to him for him to go that far to remove me from his life. We finally talked and he said it was only until he got his thoughts together and didnt want to be bothered with anyone. I finally let out all my emotions in an email to him and wanted to know where we stood and he said it was the end of us because he’s not happy and don’t know how long it’s gonna take him to be happy so he don’t want me waiting around for him. He said he’s not ready for a relationship like he thought he was.

      Although he told me time and time again he has not loved anyone since his wife died, he told me I made his heart happy again. We made several plans to travel together, sell our homes and buy a home together in a totally different state, travel the world together in retirement.

      It’s been almost a month since we last had any communication and it’s been a mess for me to the point that I’m now seeing a therapist. I cry most days and other days I’m angry which is not me. I don’t think he’ll ever come back and if he did, I would not take him back. This hurts too bad!

      • Jackie Pilossoph

        I’m so sorry this happened to you. I hope you realize that he did this as a result of HIS issues. This has absolutely nothing to do with you or anything you did. If he does contact you, I don’t think you should shut him out. Listen to what he has to say. Neither you nor I know what it’s like to be a widower. Please try not to cry anymore. You deserve to be with someone who is 100% sure and who will not do this to you. He is out there. xoxo!!!

  16. Pam

    I be been seeing a wonderful man for a year who was widowed just over two years ago. He had been married over 30 years. I am separated after 26 years of marriage.
    We get on so well, he never says anything comparing me to his late wife, however he still wears both their wedding rings and does have pictures of her in his house ( one of his daughters purposefully put a new one up the week after I met her. It was a photo of her mum on her wedding day).
    Our relationship is as close to perfect as it could be, he tells me he loves me all the time, he sends me love messages everyday via text etc telling me I’m beautiful, he is romantic and attentive We live about 20 miles from each other and because of work and that I have youngish children at home still, we spend evenings apart a lot of the time.over the last 6 months I have supported him financially when he was between jobs, supported his kids when they have been in turmoi.. However at least once a week he will text me saying he isn’t good enough for me, he thinks I should get a man more worthy of me and that he will leave me alone. He has even accused me of not loving him ( on the evening of the day he had booked days off for a joint holiday and we had just been away on a fabulous weekend)
    I have never said anything like this to him. He is wonderful and I tell him all the time how much I love him. But these out bursts really hurt. I end up calling him and talking to him about how he actually feels …. he then says all he wants is for us to be together that he only wants us to be together and that he loves me with all his heart. He says he is really scared of being hurt again he then calls and texts to see if we are ok. .He has even said he completely understands if I want to try again with my estranged husband ( he lives with the woman he left me for so that’s not going to happen and I don’t want it to anyway and my widower knows that).
    I don’t know what to do. I love him to bits and I know he loves me, but these outburst are going to end up breaking us up, when there’s actually no need for it to happen from my side, it’s him pushing me away.


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