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How much cleavage are you comfortable showing?
I'm comfortable with showing almost any amount in general public. Around my parents or their religious circles I tend to be uncomfortable showing much cleavage at all as my parents and others are not terribly afraid of vocally criticising my exhibitionism.
What do you define as a lot of cleavage?
More than about two finger widths from the start of the gap to the top of the shirt. OR more than two finger widths space to insert between the chest and the shirt.
Are there times when you think a woman showing a lot of cleavage is inappropriate (for example: around children, at work, as a wedding guest)?
Professional work, church. I have no problem with displaying a bit of cleavage when I work construction. It provides a fun distraction for all involved. Some flirtation, fun looks, and I've never gotten a complaint from the male onlookers.
I guess the more professional the dress/occaision then the less cleavage.
Do you form an opinion of someone who is wearing a top that shows half of her boobs? Depends on what she's doing. If she is a receptionist in a professional office is see her as tasteless. If she's working out, shopping, or doing other casual activities I see her as fun.
I like seeing cleavage and I enjoy showing it. Growing up and at my conservative college the girls were not allowed to wear any collars that went more than 2 finger widths below the collar bone. I relish seeing and showing cleavage now. I think it's partly a rebellion of sorts.
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"Always learn the rules so that you can break them properly." Dalai Lama
My Karma just ran over your Dogma. 
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