Dating a Widower: When Will He Be Ready to Love Again?

Posted by in dating in midlife, online dating after 40 | 2 comments

When you’re dating a widower, how long does it usually take for him to feel he’s ready for a committed relationship again? 

Dear Sandy,

I have been divorced for three years. The first two years, I worked on myself to recover and get to know myself again. Last January, I felt I was ready to date, so I went on Match. In July, I met a man who was a widower of nine months. He knew I was looking for a serious relationship and wanted to meet me. 

We hit it off right away and are now very very close. However, he is still on Match, and I’ve shut my profile down. That bothers me. I am the first woman he has dated in 32 years. He has been honest with me and says he isn’t ready to settle down in a serious committed relationship, even though he knows that I am.

I’ve told him that I want things to stay just the way they are. I’m not asking any more of him. We are very happy together, so I want to just appreciate what we have .

I just celebrated my 60th birthday, and he took me away for two beautiful weeks in Arizona. We also brought in the New Year together. He has been so romantic, and he said it was the best New Year’s he’s had in many years.

My concern is that he will never commit because I am the first woman he’s dated since the loss of his wife. He has never said he cares for me, but he always acts like we are “together.” He is so wonderful to me. I’m really falling in love with him but don’t want to scare him away. 

How long does it usually take a man to feel he is ready for a commitment after being widowed?  I’m so afraid that after the honeymoon stage of our relationship is over, he might have the urge to play. I don’t want to waste time or have my heart broken. I hope you can give some advice to me about dating a widower.

Thank you,


Dear Debbie,

First, kudos to you for taking the time to focus on yourself for the first two years post-divorce. So important. I did the same, and it has improved the quality of my life exponentially.

In terms of widowers, each one must be looked at as an individual case.

No two people are exactly alike and process in the same way. Widowers vary in their readiness for dating and relationships. Some never move on, and others date almost immediately after loss with mixed results.

Now, let’s look at the relationship you’re in with this widower, knowing that you met him only 9 months after losing his wife. Unlike you, he didn’t take much time to heal before dating. He did tell you at the start that he wasn’t ready for anything serious.

I’m afraid that you may have met him at the wrong time. 

When you start dating someone who’s not on the same page as you, it’s nearly impossible for him to come around and be what you need him to be. It’s far more effective to begin dating someone who is emotionally available and build from there.

What happened has happened, and your gut is telling you that your feelings for him are stronger than his for you. He doesn’t say he cares for you, but he is showing his affection through his actions. He’s still on Match, and you’ve shut down your profile. You’re scared he’ll tire of you and want to play. You may or may not be right. But, your intuition is smart. Don’t override it.

Have a courageous conversation with him about how you feel

Know what you must have in a relationship, and don’t compromise that for anyone, no matter how awesome they are. I suggest you have a courageous conversation with him about your feelings and concerns. He may surprise you and tell you that he is falling in love with you, too. And he may also say he’s not on the same page. Be prepared for any answer. As painful as it might be to hear that he doesn’t want what you want, it will be much better to know the truth now and walk away with your dignity intact than to keep hoping he’ll somehow come around.

If you need further support and would like to book a session with me to help you craft that conversation or to assist you in moving on to find a man who is available to love you, click here:





  1. Hi Sandy: I’m a widower of 19 months and thought your advice was spot on. Each circumstance is different. In my case, I waited 12 months after my wife passed before I began dating, Since then, I’ve dated a dozen different women, including one fairly serious relationship that didn’t pan out, Those experiences with some delightful women allowed me to reconnect with my masculine identity and gradually reenter the dating world after 30 years of marriage, They prepared me for the woman I’m currently seeing who I believe could become my next wife. If I had met her six months ago, I wouldn’t have been ready, As they say, timing is everything, Best wishes, Brent,

  2. Brent,

    Thanks so much for sharing your story of dating after loss. It’s so good to hear about your journey on the path to finding love again. You opened your heart, you continued to date until you were ready to meet the woman you’re with today.

    Wishing you lots of continued love and light,


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