Dating A Widower – Red Flags To Watch For And Avoid

This woman wrote to me about dating a widower and red flags she found. My view point is completely different than hers – here’s the whole story.

The Downside of Dating a Widower

red flags dating in your 60sDear Ronnie,

Help! I am a widow, now dating a widower for 3 years. My intuition told me not to date him as it was only a few weeks after the death of his wife when we first met. At that time he told me it was a long good bye and he was ready.

He is a good man, and different from anyone I have known and cared for.

I have met all of his family and friends. He cleaned out ‘her’ house and only has a few small pics of her around which do not bother me. He calls every night. And he pursued me hard when we first started dating.

Now I think he was in shock!

Last month, he told me he is committed to our relationship and wants to move forward with me as he ‘doesn’t want to lose me.’

Now he is eluding to the fact that he wants to get stronger in self and is seeing an EMDR therapist for trauma. He lost a lot of people in his life in a short time. His late wife died of ALS and it was ongoing for almost 5 years. He was her sole caregiver.

Helping Him Heal

I wanted to help him and he has really helped me in opening up my heart to love again. But, I have read a few articles (yours included) that read, if you help a man while he is weak, when he gets stronger he will leave you as he does not want to remember this time.

I believe he is still grieving as they were married for 36 years.

I’m looking for a man who is emotionally available and ready to make a commitment to me. Either with a ring or moving in. We discussed this and he has even looked at houses with me.

But something feels ‘off’. I’ve been told since he is not an alcoholic (my previous relationships) that this relationship would feel different. All my friends and family like him.

Something Is Missing

widowerBut I am ready for an partner to share fun times with now. I want to travel and play! We do these things, but something is missing.

I know it will be hard to break up with him, but I believe at this point I am setting myself up for more heartbreak?

Help! What do you think?

7 signs a widower is ready for love

Seeing the Flipside

Hi Mary,

Your question has confused me. You told me several things about your widower that are all GOOD SIGNS!

  • He has included you in his life
  • He told you he’s committed to your relationship
  • He’s looked at houses with you
  • He’s taking care of himself to heal and be stronger

What’s happening about dating a widower – red flags aren’t waving that I can see. He is not showing any of the signs I point to about a widower who is NOT ready –  at least that you have mentioned.

Getting Help Shows Strength

dating over 60Getting EMDR therapy is not a sign of weakness – it’s a sign of strength! He’s working to better himself and heal from the losses in his life. He has a level of self-awareness many women would love.

The weakness I spoke of in dating a widower – red flags waving is when a man is in the throws of grief and can’t help himself. He can’t function and doesn’t feel social. or he’s angry and takes it out on you or everyone.

None of this makes a man bad, just not relationship ready. But this doesn’t sound like your widower’s situation.

You believe he is still grieving and he may be – it was 36 years of marriage. That doesn’t mean he isn’t ready for you.

The long process of ALS is a different sort of passing then when someone dies in a relatively short time frame. He might have been ready for you then and still is.

Additional Good Points

  • You have fun and travel together
  • Your friends like him
  • Your family likes him.

The only thing wrong in your mind is that “something is missing” for you but you can’t identify it.

Yet, you didn’t say he’s keeping you a secret, living amongst his deceased wife’s things, or not including you in his life. You didn’t say he won’t commit, is evasive, or depressed. You didn’t say he has sexual problems, isn’t generous, or has no time to be with you.

You’ve been with him for three years. What part of being your partner is he not delivering on?

Hear This with Compassion

dating over 60I have an idea that might throw you off and be a little shocking to you. Here’s my take on this perplexing situation.

Please hear this next part with kindness and compassion. I say this because I’m thinking you really want an answer if you wrote to me about dating a widower – red flags.

It’s possible you are the one with the problem.

You don’t leave a good man behind who is committed and loving because something is missing but you can’t say what it is. If you can’t put your finger on it, that something just might be…you.

The Excitement of Drama

Perhaps you are used to the drama of dating an alcoholic – you wouldn’t be the first woman drawn to a tumultuous relationship and feeling that is normal when it comes to love.

Uncertainty creates excitement related to having problems and then making up. Some people find feeling off kilter romantic. Some women prefer the heated passion of “make-up sex.”

Another area to consider is your own family. Did you grow up with a lot of drama in your household? Did your parents have a lot of fights or drama? Does stress or uncertainty make you feel more alive?

If I’m off in this idea, my apologies.

Why dating as a widow can be difficult

Before You Leave Him

But before you walk away from a good man you love and enjoy, figure out what is missing. If you don’t, you will likely repeat this pattern. That’s why you might as well learn this lesson now then with some other man.

If you can’t point to the problem with dating a widower or red flags you see, you might ask yourself what else might be holding you back.

How to Find What’s Missing

dating a widower red flags1. Make a list of what is good in your relationship.

2. Make another list about what you liked in previous relationships.

3. Make a 3rd list about what you want to avoid in a relationship based on your past relationships with alcoholics. What didn’t work and made you miserable?

Next, look over these lists with a clear head. What do you notice? What stands out? What pattern might you see now that you never thought of before?

It might take some time to catch on to what you feel is missing. You may need to journal several times to process this. Or talking to a therapist could be helpful to sort this out.

The answer you need is there for you about what’s missing and it’s your job to figure it out. I’m not sure you can blame this problem on dating a widower – red flags.

Look within at your own life and history. Consider your expectations. Give it some thought.

Wishing you love,

Single for too long, Ronnie wanted to find love. She put her skills from personal development and her spiritual path to work, dating 30 men in 15 months to meet her adorable husband Paul. Discovering the keys to manifesting and midlife dating, she founded It’s Never Too Late to help smart, successful women find love or live an empowered and magical life. Ronnie Ann Ryan, MBA, CCC, is a Certified Coach who has helped 1,000s of midlife women with her Love & Magical Life Coach services. She’s the host of the Breathe Love & Magic podcast and has been featured on NBC, ABC, & Fox News, NPR, BBC, eHarmony,, and Connecticut Magazine among others. Also, Ronnie is the author of 6 books which are available on Amazon.

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