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The answer to these questions could surprise you in how much you honestly care for your friend.   Would you mind talking about your own underwear with this person? If not, you might be better off just going along waiting for your friend to start this conversation.  Constantly talking about urine, diapers or putting on songs relating to wet pants, incontinence, water or having your friends ring tone be one of those songs is not a good subtle way to get her/him to start the conversation.Please respect if (s)he does not want to initiate the talk. What is the goal of the conversation? Is it to have the person cut back on their diaper usage or completely rid themselves of their diapers? Or is it some other goal covered that deals with their diaper use? Do you want to be supportive, and if so how much? Think honestly how much support you can give, as diaper wearers and handling them will take a lot of psychological and physical help from friends, and can be anywhere from helping them change their diaper to covering up their lie that they might not want exposed to others to shield the wearer from obvious psychological damage if they spread it to others who spread it even further. Turn off your phone to show you care about a private conversation. Let there be room for your friend to tell a sad story, cry and confide in you without disturbances or other appointments coming up. Your friend might have had this conversation before and be confident about wearing diapers, but it might also be the first time they have this conversation outside of close family.  Read the rest of this guide. Consider the intimacy of the help you want to provide, where your limits are as well as bring up situations where you have doubts on how to handle it. Express your friendship to and with them. Let your friend know that you like her/him because of certain reasons including their personality and that wearing diapers does not change your viewpoints of your friendship with them in any way. Ask what word they would prefer you’d use. Some prefer calling these absorbent pants diapers, while others don’t like the connotations these words give and prefer pads, briefs or absorbent underwear…sometimes, however, the wearer might not even like any of those terms to be used and would like another piece of clothing name to refer to it as. Find a word that suits you and your friend's level of discretion. Try on one of their diapers, to see how your friend feels when wearing them if you can stomach the idea that you are wearing one and can be assumed to be able to take it off confidently without a fuss. If you are an inquisitive person, you might ask your friend if you can borrow a diaper to try it on yourself, which can open the conversation to let your friend show their expertise and advice on their ability to wear a diaper and make them feel accepted and on equal footing with the remainder of the people in the world. Use the guide in How to Wear a Diaper to find out how you can wear a diaper like them.
Ask yourself some questions about whether you consider your friend to be a close friend or not? Prepare the first conversation. Plan the conversation to be in a private setting without other people around.