Addressing "embarrassing" aspects of your background

[tf01]

I realize that it is important to become ok with anything "embarrassing" or "shameful" in your background. And, that sharing these things openly, honestly and with confidence during the dating process, can actually be a positive as this is the definition of being vulnerable during dating.

But that said:

When is it a good time during dating to reveal something like this?

Any suggestion on how to broach the topic?

I tend to reveal this only when it is getting serious. The times I have brought this up it took significant emotional effort on my part. But, at least in two cases, my girlfriends seemed unfazed.

[Vytas80]

Can you please be more specific on what do you find "embarassing" or "shameful"?

[bwong]

I use to think that me dropping out of high school was a big deal and that I moved to the city I'm living in to get my shit straighten out was embarrassing/shameful so I know where you're coming from. However if people were to ask me why I moved to Vancouver, I'd tell them exactly that: to get my shit straighten out. It's more important how you project and portray yourself with whatever you think is "shameful." In reality it probably isn't as shameful as you thought. Try to reflect on why you think its shameful, accept it and move on. If they ask something regarding it just be honest.