Coaching a Widow Who Wants Another Chance at Love

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another chance at love

In this podcast episode, I coach a widow, Katherine, who wants another chance at love after losing her husband three years ago.

On today’s podcast episode, I’m coaching a widow who wants another chance at love. This is a one-time session with “Katherine”, a woman I’d never met before. My hope is that through this coaching session, not only will I have helped Katherine with her dating challenges, but you will find parts of her experience that resonate with you as well. 

EP 611: Coaching a Widow Who Wants Another Chance at Love

“Katherine” (not her real name) wrote in to the podcast:

I am sixty-two years old, and I was widowed three years ago. I’m grateful to be retired and in excellent health. I was married to a wonderful man for thirty-four years. Our four adult “kids” are doing well, and I enjoy an active lifestyle – swimming, spinning, yoga, hiking, and gardening. I also work on ongoing art projects, volunteer at the theater and at church, and help elderly residents and dogs in my neighborhood.

While I have good girlfriends and male acquaintances, I yearn for a man to date. At times I feel like a fifth wheel with my married friends. I crave a relationship with an honest man to share intimacy and enjoy this active and healthy chapter of our lives together.

I also have the curse of being a retired nurse, and I’m learning to stop being the caregiver after dating a man with significant anger issues and two men with drinking problems. A suitable man to date has not yet fallen from the sky! Should I continue to live my single life, or dredge up more courage and optimism with the online dating game?

Here are some of the challenges Katherine experiences as she first began to date:

  • Wanted validation from men at first and was afraid men wouldn’t find her suitable.
  • The first man she dated had never married, and he had anger issues. She tried to fix him, as she was a giver and caretaker all her life. He became very clingy and she finally ended it.
  • The breakup was bad – he was pushy and angry.
  • The second man she dated she met while swimming, and it turned out he was an alcoholic. He was also never married. 
  • Both men had family relationship challenges and hadn’t done work to heal.
  • The second relationship ended more kindly and with clear boundaries.
  • She gave emotionally and monetarily with all the men she’s been with. She now realized there was a pattern here, and she needed to develop better boundaries and increase her self-worth.

We discussed what partnership looks like to her and came up with a list of must-haves and deal breakers as she gets back out there to date again.

Green flags to look for on dates:

  1. Values relationships with family and close friends
  2. Values health – diet, exercise
  3. Volunteers and gives back
  4. Kind and compassionate to others
  5. Enjoys learning and new experiences
  6. Open minded/self-aware

Red flags to look out for when dating:

  1. Poor family relationships
  2. Not a lifelong learner/rigid in thinking or political views
  3. Doesn’t value health – smoker/excessive drinking or drugs
  4. Conflict-averse
  5. Can’t be vulnerable, lack of self awareness

Katherine’s Homework to help her have another chance at love:

  1. Go out and have more deep conversations with everyone and especially men in your life.
  2. Keep your red and green flags in mind when on dates, and ask questions that help them disclose more about whether their values align with yours.
  3. Be present to who you’re dating. Don’t try to figure out whether they’re your future partner.

What did you take away from this episode? Please share your thoughts below.

Watch this episode on YouTube

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Get a copy of Sandy’s books, Becoming a Woman of Value; How to Thrive in Life and Love and Choice Points in Dating; Empowering Women to Make Healthier Decisions in Love.


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