Hi y'all!

So here's my decision: I'm shaving my remaining hair off at the end of the summer and ordering a vacuum wig. And I'm actually really excited! YAY!

Here's the thing. When should I tell a guy that I'm wearing a wig and my head is shaved? Do I do it before we get into a relationship? On the first date? When I sense things are going somewhere between us? I'm currently flirting and kinda dating this one guy who I met relatively recently. He doesn't know about my hair loss and I haven't mentioned it to him yet since my hair is still on my head. I'm just not sure what to do though. Do I tell him before I even shave it off? Do I wait to shave it off then tell him? Do I tell him now or wait until things progress? I don't know! We're not in a relationship. We've only been on a couple of dates and several group hang outs. We flirt a lot. I don't know if I should even tell him because I don't know what this is going to turn into.

I got some feedback from some people who know about my hair loss, and this is when they think I should tell a man.

Mom: Only when things get serious.
Grandma: Never. (Oy!)
Best Friend 1: Only when I feel comfortable.
Best Friend 2: Pretty soon, before things get serious, and if he doesn't accept me then he's not worth my time.

I think I should probably tell a guy sooner rather than later, it's just that I'm not sure when. I'm not sure if I should wait a little until he gets to know me and care about me more, or if I should just get it out there right from the beginning so there are no secrets to be announced later.

Please give me your advice and tell me your experiences! I know not all guys will accept this, but I'm confident enough with myself to know that it's not going to prevent me from meeting someone who will ultimately love me either way. I'm just not sure when to let them know.

Thanks! =)

P.S. - I was thinking about just going out with a shaved head and NO wig too just to see what it's like without the hassle.