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Your past is irrelevant. His "third is the charm" comment seems flippant and dismissive, but you won't know until your next encounter (w/o the sex).
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I think a lot of older people who are divorced, widowed, never-married, prefer to live alone, as it is not all bad living alone. In addition, the internet is a great companion. Of course, if someone falls madly in love with someone that is different, but I would not want to marry someone whom I just had an OK relationship with, even if they were a good person. Also, I think one's financial situation is a big part of it. Many people may not be able to afford to live alone, and will marry Mr. (Half-Right) to help with expenses, etc. I think even a lot of younger people are staying married because of financial reasons, kids, etc., and may not be happy with their spouse. I live alone and I like it, for example, if I go to the store, etc., I don't have to tell someone where I am going, when I will be back, etc.
Yeah, I'm still taking counselling, because I still don't like my body much. I'm less worried about my boyfriend dumping me now because he hasn't complained about my breasts till now and it seems that he finds me attractive. At least that is what it looks like. Things are going well 0otherwise, too, so maybe I keep worrying unnecessarily :s
I feel the same as Jazzari.
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wear your heels you'll look better in them