Advice on discussing emotions?

Hey guys, new to the forum! A bit of backstory first. Back in my early 20's I dated a gal for two years. We remained very close in the years since, and I've remained close with her family too. The past month or so we've been discussing the possibility of getting back together. We're both a little nervous about it, as we've both developed a bit of a "history" and past hurts in the time since, her more than me, that we agree will need to be discussed. The problem is that she is the type of woman who finds it very difficult to discuss emotions, even with those she's closest to. I've been told by several female friends that I'm a great listener, however, as a guy, I'm not used to being the one to initiate discussions involving emotion. Any advice, especially from the women on the forum, on how to help her feel safe doing so? Thanks!

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