LILY Letter 72: The Courage to Love Again

August 23, 2022

One of the most common refrains we hear from mid-singles is “I hate dating.” In the vast majority of situations, the individual doesn’t actually “hate dating.” He or she hates rejection. He or she hates being judged. Rejection in dating often feels deeply personal, and it requires a lot of emotional maturity to cope with it in a dignified way. The possibility of rejection or loss is why love takes courage. The effort to find love requires an investment of your heart, knowing the risks. People take those risks because loving and being loved produces the sweetest feelings in the world.

Many mid-singles are carrying the pain of past emotional injuries and are particularly sensitive to being hurt. This is understandable. But if we allow these past injuries to intrude on the present, we limit our own opportunities and contribute to our own misery. Part of moving forward after pain and loss is to accept the fact that risk of future pain is the price of finding love—and accept that if you try again, you may experience more pain.

It is always your decision whether to move beyond past hurts and take another chance on love. Some conclude that they have had enough pain and it is no longer worth the risk. While that may feel like a sensible decision, it is also important to consider that you may be settling for a life that is not as full and joyful as it might be.

If an enduring love is still on your bucket list, perhaps these suggestions will help you to move beyond pain and into power:

1. Work on self-confronting and accept your own part in prior relationship problems. This does not mean you were exclusively or even primarily to blame. But no one does relationships perfect, and it is certain that you could have done better. It is more effective to leave blame out of your thought process and focus mostly on your own thoughts and behaviors. The only person you have full control over is yourself; so it is empowering to focus on how you choose to show up in relationships and make intentional efforts to show up better in future relationships. That is far more enlightened than constantly finding fault with someone you have no control over and who may not even be in your life anymore.

2. Heal from Trauma. Healing involves telling your story to trusted friends and finding strength in their support. However, it is sometimes tempting to become too reliant on other people agreeing with your interpretation and expressing sympathy. Over time, it is important to adopt new interpretations and simply recognize that your losses are part of your journey. If you are becoming triggered in new dating relationships, that is an opportunity to release the associated trauma. Allow yourself to feel the feelings and work through them so you can let them go.

3. Get Coaching. Even if you don’t feel ready to date, a good coach can help you to understand your life experience better and look forward with hope—actively working towards a brighter future. If you like our approach to healing and relationships, we invite you to take advantage of our coaching services.

Building relationships after loss requires courage and faith. We hope and pray that you will have an overflowing supply of both.

Enjoy this week’s featured video which focuses on active healing towards moving forward and creating new healthy relationships titled: “Let’s Get On With It” and the associated podcast: “The Power of YET!” Our short of the week is “Heal Intentionally.” 


LILY Pod Episode 84: The Power of YET! (29min)

LILY Tube Video: Let’s Get On With It (10min)

LILY Tube Short: Heal Intentionally (1min)

To discover what coaching can do for you, visit LILY Coaching and set an appointment with one of us. We've got you!

To get a copy of "Intentional Courtship" on Amazon and create more love in your life in 2022, visit 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!

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