Meeting up with an old friend can inspire a whole range of concerns, such as “What are we going to talk about?” or “What if I run out of things to ask?” Having a tentative outline of things to ask a friend whom you haven’t seen in a long time may help ease some of the nervousness you feel and alleviate awkward silences. Cultivating a healthy dose of curiosity can deliver benefits to you as well, such as improved health and a richer life experience, notes clinical associate psychologist and psychology professor Todd Kashdan, writing for the Experience Life website.
Your friend may have started a family, which is the source of much love and pride, and may want to share this with you. Ask your friend about marriage and any children. Alternatively, ask about your friend's family of origin, particularly family members with whom you’ve had interactions. If your friend has children, find out specific information about them, such as their ages, grades in school and special interests.
Many people love what they do professionally and enjoy the opportunity to talk about it. Asking specific occupation-related questions may spark a lively discussion about the industry itself and the contribution your friend makes on a daily basis. If your friend is not excited about work, and expresses this disinterest to you, provide a listening ear so that your conversation companion can vent and voice frustrations.
Past experiences shared by you and your friend will, more than likely, be a good subject to bring up when you reconnect after a long time. Bring up any funny moments from your time spent in school, at a previous job or wherever the two of you shared experiences. If possible, try to keep the memories light and funny, and avoid bringing up shared experiences that may be too heavy to discuss while reconnecting for the first time in a long time. Pay close attention to cues given during your discussion; if your friend decides to take the conversation in a different direction, then, by all means, go with the flow.
Personal Growth and Interests
If you and your friend are having a good sit-down conversation, you may have time to go into depth about important matters, such as personal growth. Ask your friend about significant life lessons, or if there were any romantic or familial experiences that have helped form the person your friend is today. Is there any pertinent advice this person would like to share to help you be successful in some area of your life? Asking about these experiences will give your friend a chance to share deeper information with you and will enable both of you to walk away with useful information from the encounter.