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Six Dating Mistakes for Widowed Men (Who Want Love)

Kimberly Hill - Men's Dating & Relationship Coach

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Kimberly Hill, a men’s dating and relationship coach, addresses widowed men who feel stuck about dating again and explains that loss is not the same as divorce. She outlines six patterns that sabotage new relationships. She emphasizes that being present isn’t betrayal, new love won’t replicate the past, reengagement is a muscle, and moving forward requires self-permission and honest, gradual emotional openness.

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02:56 - Mistake 1 Past Tense
04:31 - Mistake 2 Filling The Void
06:06 - Mistake 3 Comparing Her
07:34 - Mistake 4 Isolation Habit
09:08 - Mistake 5 Seeking Permission
10:40 - Mistake 6 Closed Heart

20 Comments

@Being_Joe 1 month ago

Thank you for acknowledging that being widowed is not the same as divorce. 43, I wish there was more content geared towards widowers that was not just dating advice. But it is nice that someone can see there is a difference.

@donlopez3185 2 months ago

My wife of 33 years died tragically a year ago. I started dating a divorced lady that I knew a little (used to work with her X), and my adult children hate me for it. It offended them that I took another woman to their late mom’s backyard to enjoy our pool. They even tell me their late mom wouldn’t want me to have a girlfriend knowing how it hurts them. Well I’m not giving up a beautiful, loving lady to make my kids happy.

@coreylarge3628 6 months ago

You hit the nail on the head, I definitely feel called out. But as hard as it is, I’d rather just stay alone after losing my wife than risk diluting the amazing marriage we had by risking another relationship.

@healingstrings 6 months ago

I’ve been widowed three years, and I am in a season of enjoying my time alone. There’s a difference between isolating and enjoying and building a full life as a single man before you meet someone.
That said, I thoroughly enjoyed this video, and agree with all of it! There is a real temptation to withdraw from social circles. after being a couple for so long. You sort of feel disenfranchised from the world, and wonder where your place is in it. But we must move forward to find out those answers those questions.

@Modernist-p1f 4 weeks ago

What a great video. Everything is so well said. My wife of 22 yrs passed early in 2026 and due to the dynamic in our struggling marriage for years before her stage 4 cancer diagnosis in 2023, and life after her diagnosis until her passing, I haven’t had any intimate contact with a woman for ~6 yrs now and it’s getting heavy on me. I’m not just a one night stand kind of guy. I know I don’t feel ready to fully open to another woman but this video helps me understand why and I know I can see myself making some of those mistakes. Keeping the mind very busy and the walls are still up. I read folks finally getting ready 5 yrs after the shock and that sounds too long but I know myself and I’m probably in that category as well. This is a video I’ll need to rewatch every so often. Thank you

@jtrettin1 6 months ago (edited)

I was widowed almost 5 years ago when my 46 year old wife passed away from cancer. All the points in this video are what go through my mind daily. It's so good to hear them explained so well with some tips on dealing with them. The Permission item resonates especially with me since my teenage children are very averse to me ever dating again. To not jeopardize the great relationship I have with my kids, and their grieving process losing their mom, I just need to concentrate on them right now. Maybe someday I will be healed enough to love again but it would have to be a heaven-sent situation, a genuine miracle.

@KenW997.2 5 days ago (edited)

I just turned 60 and recently lost my wife to cancer after 32 years of a fairytale marriage. We never argued. We maintained the same passion and intimacy at 55 as we had at 35. It was amazing. And now, as I'm about to retire and spend the rest of my life chasing her around the house, she passed away. I've spent the last little while consuming info on dealing with the grief and moving on and can say your video is spot on. I look forward to going through your library of information.

@retiredude 3 weeks ago

Thank you for your insight. I am a widower 2.5 yrs struggling to put my life back together. We were married 50+ years. The later years, due to illness and no fault of her own, were a difficult struggle, today l am liberated. I have no desire to remarry but a companion and sharing time with another woman ìs rewarding. In the meantime I'm struggling with where l am, where I've been, and where and how am l going to get to where I'm going. I recognized this takes time. To complicate my situation, l have a 50 year old offspring that has an issue with my interfacing with another woman. The whole situation is difficult to navigate. Time will take care of things. Thank you for letting me vent.

@JonC-u5m 4 months ago

Hello Kimberly. Just found your video. I lost my wife of 40 years to ALS in 2023. I am just now feeling like I would benefit from finding a companion and am considering dating again....though my knowledge is several decades old.🙂 I have been going out with friends....usually couples at dinner or events. Also, went to grief classes and a counselor. I confess the "empty chair" next to me is always on my mind. I am looking forward to getting to know someone for who they are....not a replacement. And while dating scares the heck out of me (even holding another woman's hand would be...well, weird), I want to see who might be out there. For better or worse, I have no kids and no in-laws alive to complicate things. I will keep your 6 dating mistakes in mind. It was a great video and really zeroed in on the emotions and fears of dating in my personal situation.

@richcohan4737 3 weeks ago

Just found you, Kimberly. Thank you for being here for us…the widowed. I lost my wife of over 40 years about 13 months ago. The biggest lesson I learned when I decided to try dating 10 months after losing my wife, was I thought I was ready for a real relationship when in fact (easy for me to admit this now) all I wanted and was ready for was female companionship. I fell hard as did the woman I started dating. We were together 2 months and I messed up all over the place. I tried to convert the relationship to friendship as she is awesome, however, not to be.

@JuanaCarmen-k6y 6 months ago

Excellent video. Been a month since my 5-year relationship ended , still trying to heal and move on, but it’s not easy.

@s.joseph-747 6 months ago

Kimberly, This was one of your best videos ever. Any and all widowed men need to see this one. I'm sure you made some men shed a tear and realize that it might be time to move on and that's ok. You just changed some lives. Have a wonderful day and thank you.

@Wiseblood2012 6 months ago (edited)

Therapy might be useful here, I usually don't advocate for that. Getting help on the path to being an whole person when you suffer a loss like this is the way to go.

@paulfowler3416 6 months ago

My wife died last year after 5 years of illness. 46 great years together and I would not do anything differently. Now I am ready to move on and feel that warmth and contact again, but I worry about my not far off 40 year old daughter’s reaction - we have a great relationship and are friends as well as parent and child. But she also was very hard hit by her mum’s death.

@michaelavina2230 4 weeks ago

I lost my wife 3 years ago after a 45 marriage. Over 2 years of dating I’ve met 2 women who I developed a deep connection with but, when each wanted to become physical I couldn’t. I’ve been checked out medically and am fine medically. I’ve started seeking a therapist and he says my body is rejecting people who are not right for me. Where do I go for help?

@JohnDevitt 2 months ago

You're nailing this Kimberly, and I'm speaking from the vantage point of someone who's been a widower for 8 years. I know mileage may vary, but I feel that I may now be finally ready for a new chapter. At this stage one also knows that life guarantees zilch. But as long as we're on the field we gotta play. Enjoying your videos. Thank you!

@natejackson4791 6 months ago

As recently separated, you make some distinctions that parrelel my current situation.

@unendingdark 1 month ago

Wow. Every single one landed with me. Some I've worked on before dating, some learned while dating, and the most recent trying to figure out why I feel the way I feel. Now I can put it into words. Thank you so much. Now I can begin to work on them.

@SBarnes1216 1 month ago

Kimberly - your insights and advice are just incredibly on point and very useful. You are just so wise. As a 67 year old widower I have learned so much from you. Thank you so much!!!