First, let me say congratulations! Most people never come to the point of actually addressing directly a difficult situation. It seems easier to sweep it under the carpet and tell yourself it will work itself out without you having to do anything. In the meantime you suffer and your relationship with the person suffers. Getting back into relationship with the person requires action, but the pay off is worth it.
So you feel that you are ready now. Question is, how do you proceed? This Moment of Truth conversation deserves focused preparation. It will help to take time to answer these questions:
1. What happened?
Answer like a scientist who is observing and not ‘getting inside anyone’s head.’
On New Year’s Eve, you and three younger people used chalk to write words and draw on my car. You said it was meant as a joke. You did not offer to clean my car afterwards. I went to the car wash, but the writing/pictures damaged the paint job. The specialist said my car would have to be buffed which costs $150.
2. Remember how you felt when this happened.
Were you angry? Embarrassed? Disappointed? Write down your feelings. You will want to tell the person how you felt -- not as an emotional weapon, but as information. The person needs to know the emotional cost of his actions.
I was angry that you would mess with my car and also disappointed that you didn't offer to pay for the cleaning when it became obvious that the chalk had damaged the paint.
3. What specifically do you want?
I’d like for you to pay to have my car buffed. And I’d like you to apologize.
4. Write down notes for the conversation.
Make notes for the conversation. Keep the ending in mind and get yourself ready to listen to his side of the story. Your notes will help you stay on track and stick to your guns when it comes to asking for what you want.
5. Consider when to have the conversation and then schedule it.
When is the best time to talk to him? You may need to set an appointment so there is adequate time to talk (yes, even if he is a family member). If possible, meet with him face to face in a private place. If you can't meet face to face, then talk with him on the phone. In a situation like this, email and texting are not good options.
Remember that the goal is to get back into relationship with the person. It will probably be a relief not to have to step over this anymore and be on the way to regaining the trust that was lost.