I have become reaquainted with an old friend and may begin to date him.  He knew me a long time ago when I had long think hair.  I am completely bald now and wear a wig.  So far I have been able to stay clear offering side hugs and not going on adventures that would cause my hair to get wet or blow in the wind.  I cant keep it up much longer because he knows I am an active person.  When is a good time to tell him about my hair loss? I dont want to say anything unnecessarily just in case our relationship does not take off.  But it feels deceptive to not tell him and then we start dating. Any suggestions?

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My advice is to tell him what is going on with you. If he really likes you, he will find reasons to stay with you. You can’t hide the fact from him for your whole life. 

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