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I cannot say "I'm sorry"

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Hi guys,
I have always been aware that I cannot say "I'm sorry" in situations that involve emotions. I have no problem apologizing for stepping on somebody's foot or for being late, but as soon as it comes to me messing something up emotionally and having to apologize, I just can't. Only if the person calls me out on it, I push out an insincere "sorry" but I know I don't mean it. I do regret the thing I did inside, but I don't have means to express it.
It kind of culminated a few minutes ago when I broke my friend's mug that bore a deeper meaning to her. I was immediately thinking of ways to fix it, Googling the mug, ordering a new one for three times the price she paid for it, but I couldn't get myself to say sorry explicitly. I basically shut myself out of the room immediately, busying myself with the phone so that I didn't have to confront her. Only after her boyfriend got mad at me for not having the 'common courtesy to say sorry, please or thank you, like ever' I managed to squeeze out anything of the sort (to be fair, I never noticed I lacked in the other 'common niceties' departments). I do truly feel horrible.
I come from a very disconnected family that never expresses feelings and never goes through that 'making up' phase after fights, and I've always thought that was behind my behavior. I do understand though that I can't just expect everybody to be fine with no expressed apology my whole life though.

How do I work on becoming better at saying sorry and meaning it?

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