Dear Chara: Dating After Divorce or Disappointment — How Do I Trust Again Without Losing Myself? 11/20/2025

Dear Chara, I’ve been divorced for two years. I want to love again, but I’m scared. Every time someone gets close, I find reasons to pull away. Part of me wants companionship, but the other part is afraid of repeating my past. How do I move forward without losing myself again?

Dear Wounded but Willing,

First, I want to honor your bravery. Healing and hoping again at the same time is hard — but it’s holy work. God never meant for your story to end at heartbreak; He meant for it to be rewritten through healing. While it may seem challenging to move past this point, it's not impossible. Here are some things I want you to consider. 

• Grieve before you give. Don’t rush into love to avoid loneliness. Healing isn’t the absence of pain — it’s learning not to build your life around it. If you have not grieved the last heart break, you will want to go through that process first. Loss is loss, when we lose something, we must grieve. 

• Date as a whole person, not a half. You’re not looking for someone to complete you — you’re looking for someone to compliment your wholeness.

• Set new boundaries from wisdom, not wounds. Fear builds walls; wisdom builds gates. Boundaries that breathe allow love to flow without control.

• Remember: new love doesn’t erase old lessons. You can trust again and stay discerning. Forgiveness doesn’t mean forgetfulness.

• Let God reintroduce you to you. Before you fall in love again, fall in alignment with who you’ve become.

• Trust happens naturally when it's taught correctly. Trusting people should happen naturally because everyone should be innocent until proven guilty. We error when we already punish someone for something they haven't even had an opportunity to do or not do. Additionally, you can trust when you don't have unrealistic expectations of a person. When you go into a situation with 'your' ideas of how it will or won't work (good or bad), you can set yourself up for disappointment. Yes, have your standards, but know that having standards does not mean you do not trust. You go in the situation with an open heart and open mind, but you pay attention to red flags. 

The greatest suggestion I have for you is this, as a dating woman (or man), you will want to get some mentorship in the art of dating. This can be very beneficial to you and your healing. Many people date based on their perceptions of what dating entails, but healthy people date from knowing the art of dating. Use your single time learn and build, this will help you heal. 

As I close, I just want to share that your past prepared you, not punished you. When you heal, you attract differently — not because they changed, but because you did. The next chapter will meet you where your growth lives. 💛 If you want more information or help walking through this process, let me know, I would love to help you. God bless you! 

~Ask Chara~ 

Ready to Heal, Learn, and Date with Confidence Again?

If you’re coming out of a breakup, divorce, or a season of discouragement, you don’t have to figure everything out alone. Sometimes all you need is a safe space to process, rebuild your self-worth, and relearn the art of healthy, joyful dating from a faith-based perspective.

✨ I offer 1:1 Dating & Relationship Mentorship
A gentle, guided journey helping you:

• Heal from past relationship patterns

• Rebuild your confidence and identity

• Understand emotional safety and boundaries

• Learn how to date with wisdom, discernment, and joy

• Prepare your heart for the kind of love you truly deserve

If this resonates with you, you can request mentorship here:

👉🏾 [Apply for Dating Mentorship with Chara]

Your heart matters. Your healing matters.
And love—healthy, God-honoring love—is still possible for you.