LILY Letter 108: Having Hard Conversations

May 2, 2023

The kindest thing we can do in a relationship is to speak truth in a compassionate yet assertive way. However, most of us tend to avoid having hard conversations and the discomfort and unknown repercussions that can come with them. The following four scenarios are examples of why we tend to avoid hard conversations and why that avoidance can be detrimental and worse than choosing to have those hard conversations.

We personally know someone who recently lost his job and felt so humiliated and fearful of how his wife would respond that he hung out in the public library everyday hoping to find a new job before she found out. He told himself he was protecting her from the anxiety she would feel at knowing he had lost his job. Yet what will happen when she inevitably finds out that he is no longer making money and he has kept that truth from her?

We all know people in the mid-singles community who just disappear and ghost someone rather than having a difficult breakup conversation. Yet how bewildering does that feel for the person left wondering what happened? 

A dating couple may be so fearful of losing each other that they fail to have an important conversation that both are afraid may be a deal breaker. Yet do any of us really want to continue in a relationship that has these potential deal breaker issues that have never been explored? 

The same can happen in marriage where a couple simply avoids a sensitive topic and tries to work around each other rather than dealing honestly and straightforwardly. Yet do any marriage partners really want to walk on eggshells with an elephant in the room for years on end?

Most people know these scenarios are not healthy for a relationship. It requires courage to give someone you care about bad news or have conversations you know may cause conflict. Living in integrity with our values requires us to have hard conversations even though we are afraid. Honesty is essential to building and maintaining trust in a relationship. Telling falsehoods or failing to have necessary conversations for a long period of time causes a breach of trust that jeopardizes the relationship.


This week continues our "REJECTION" series on LILY Pod so you can become a master at dealing with this inevitable part of life and relationships. Last week was "Rejection is Along for the Single Ride." This week we narrow the focus to "Giving Rejection Well" and next week we will finish the series with "Receiving Rejection with Grace." Enjoy the following NEW content and have a great week!

LILY Pod: Giving Rejection Well

LILY Tube: The 4 Scariest Words in a Relationship

LILY Short: What Do You Really Want

Interested in our “Life Design After Divorce” 12-week Course? To access the entire course and join us for the LAST LIVE workshop and coaching session, REGISTER HERE:

Discover how LILY Coaching can support you. Simply email us at to request FREE consultation with Jeff or Cathy. We look forward to meeting with you personally!

Get a copy of "Intentional Courtship" on Amazon to heal from relationship loss and create more love in your life. Order your book HERE: Intentional Courtship

If you enjoy this letter, forward to a friend. Our goal is to support as many mid-singles and later-married couples as possible so please share this letter with those you love!

Love in Later Years © 2021
Privacy Policy