Decide exactly what you want to talk about and why. Think about what you want to see happen in the future, and try not to dwell on every shortcoming from the past. Concentrate on the current situation, not past ones. Try not to get too wordy — explain what you're feeling and why. Finally, say what you would like to see happen. After that, answer any questions they have. It may help to write out what you need to say before talking to this person. If you are convinced that the words won't come out right, put your written words into a letter — edited more than once for a balanced delivery — and personally give it to him or her. Effectiveness goes way up when you stay while your friend reads it, so that you can stay to answer questions. Always an excellent standard: good news by letter, bad news in person.
Pick a time and place that is both relaxing and intimate — preferably in private. If you are afraid of a harsh or intimidating reaction to your emotional question, meeting in public may help, such as a cafe where you can both sit and talk without interruption, as opposed to a sports bar. Turn off any cell phones or pagers that might disrupt the flow of the conversation.
Ask your question and be honest. It is still important to keep the other person's feelings in mind when you are honest but don't make up stories just to ease the asking. Ask a genuine question that is based on facts as you perceive them. Ask an open-ended question – that is, one that the other person can respond to without the conversation being shut down. Ask with respect and kindness.
Take care not to scare the person away or be too emotional. Avoid acting as if your life is hanging on the answer they give you. (If it is, are you a safe person for him or her to be close to?!) This is especially true if it is a new relationship. It is unattractive and makes you seem desperate or unstable. (Even if you are, you don't want to show it!) If you are melodramatic, you risk making things more complicated and less obvious. Equally, don't be cheesy or fake in an effort to act contrary to how you feel. Just be honest. For example, if you are asking someone that you have been casually seeing if they are interested in moving the relationship along, be upfront, but avoid being melodramatic.
Keep it casual. Don't put too much pressure on the other person. You want the person to be honest, and even if what they say isn't what you want to hear, it is better to know how they really feel so that you can adjust your plans accordingly and move forward with wisdom. For example, if you're asking someone if they want to be more serious and they don't want this, even though it is disappointing, it is good to know that so that you don't set yourself up to get hurt by falling for him or her too much.
Be confident and direct. Don't beat around the bush. The ability to take on a sensitive issue delicately but directly is an attractive trait that reveals your maturity. If you need time to cool down or to keep from getting too emotional, excuse yourself to the restroom, take a few minutes and a few deep breaths.
Listen to the other person completely when they answer you. Make a genuine effort to understand their answers. Look them in the eyes. This will show the person that you care about what they think. Don't preach or try to change the other person's answer. You must assume that they are speaking honestly and in good faith. Allow the other person to share what is in their heart – listen for it. Be very patient. Some people may want to tell you, but they will need to battle their own ego and concerns to speak of it. Don't try cut in and talk until you are sure that the other person has finished talking.
Be prepared to compromise. If the other person doesn't want to do what you're asking for, try to find the middle path. If they don't want to do something, ask yourself what other ways you will be happy to reassess the solution: For example, the other person doesn't want to take dance lessons 5 days a week. Maybe you could try once or twice a week? What arrangement or changes might put the two of you on the road to freedom for 5 dance lessons a week? What would that take from you, and for how long?
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