I think I've always known
I just didn't know it was okay, the aftermath of Southern upbringing.
When I started looking back on my unsuccessful career as a monogamous, one relationship really started to stack up for me - my first. It was high school, and we were both really busy people and we both wanted a weekly date and found one another very attractive and appealing, so she and I pretty much laid down groundwork on how that relationship would work, yet she did not get that it was okay for her to see other people, as long as she was open about it. Unfortunately, when she was, she'd lie about it, but when I did, i was out in the open. What she did not understand was that there was never any jealousy from me about these other guys, what upset me was the deception.
From there, for some reason, I looked again for a monogamous relationship, and after stumbling around for several years, I, thankfully, ultimately wound up marrying a wonderful friend of mine, and our friendship really is what made our step into polyamory comfortable with me.
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