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I'm totally self-made, and still working my way to real financial stability, so I get it.
Not to mention, her boyfriend is YOUR friend. Where is your loyalty to your friend to allow this to happen?
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I think that one cornerstone of your problem is that you have some kind of shame/guilt issues yourself around sex. This talk of "blaming her for her past" sounds so weird - if you can't help blaming her, that tells us you feel like she's done something wrong. You think it's wrong of her to have a sexual past. You think sex is somehow wrong. Even though you admit that her past isn't that bad, your statement clearly implies that it's still bad, and that any sexual past is bad, it's just a matter of degree how bad.