Why Do I Keep Dating Men Who Aren’t Kind?

Posted by in dating a dangerous man, dating in midlife, red flags in relationships | 0 comments

men who aren't kind

Why does Mary date men who aren’t kind? In this episode, I coach her to be able to choose men who respect and value her.

This is a one-time coaching session with “Mary”, who’s not a client. She wrote in to the show: “Most of my life I’ve dated and had been married to men that have not been kind yet I would continue to give them chance after chance and think that it would get better. It never would, yet I have found myself in the same type of relationships over and over again. I would like to figure out why I give men chances when they have hurt me more than once.“

In this episode of Last First Date Radio:

  • How to stop giving the people you date the benefit of the doubt
  • Why it takes seven times to leave an abusive relationship
  • Why it’s important for people to earn their way back into your life if you breakup and they want to come back
  • How our childhood influences our romantic relationships
  • How one deal breaker makes all the good qualities null and void
  • Why it’s important to ask more questions at the start of a relationship
  • Curiosity is key in getting to know your dates better
  • A great question to ask someone you’re dating to find out why their relationship ended

EP 586: Live Coaching with Mary: Why Do I Keep Dating Men Who Aren’t Kind?

Here’s Mary’s story about her last relationship:

They went out for about a year. At the beginning, he was kind and sweet. A few weeks later, he started drinking. She has a history of dating men with substance abuse or past trauma that they haven’t dealt with. 

She loved his family and enjoyed being with them. But when he drank, he was mean and hurtful. He was disrespectful of her, her daughter and her daughter’s  boyfriend. He even accused her daughter’s boyfriend of being sexually interested in Mary. That was the catalyst for one of the big break ups. Three weeks later, he called and asked to get back together. He apologized, but nothing changed. After seven breakups, she left for good. She misses him, but she’s been dating a new man for a few weeks, and so far, it’s been far better than the past relationships. She wants to make sure she doesn’t mess things up this time.

During our session, I asked about her family of origin. There’s a direct correlation between her parents and her fear of abandonment and confusion about what healthy love feels like.

Questions to ask yourself about your love blueprint:

  1. Who does this person remind me of?
  2. Where have I felt like this before?
  3. Why is this dynamic familiar to me?
  4. Who do I become and who do they become when we’re together?

Mary’s Homework: 

  1. Clarify your must have and deal breaker lists
  2. Keep those lists front and center for every date
  3. Address any deal breakers immediately
  4. Debrief every date to make sure it’s working for you
  5. Ask the hard questions
  6. When feeling anxious, ask yourself if it’s true and look for contrary evidence

Have you ever dating men who aren’t kind? What will you put into practice that you learned from this episode?


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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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