My biggest "what if" is "What if I had not been openly poly".
It's not a think with a SPECIFIC relationship or anything. But when my ex-wife and I opened out marriage (I'm poly, she is 'open'), it was clear that it was because I wanted to fall in love again. She wanted partners.
This level of freedom and honesty in our relationship felt amazing and I wanted to share that "option" with people, so I came out pretty early on.
I live in a community of a thousand tight-knit folks with a common purpose. Within this community, I became somewhat of the poster boy for polyamory.
My only regret is what if I hadn't done that. The first person I fell in love with never returned my feelings... or not openly so. She was married and supposedly mono. She seemed to react more to the fact that I was poly, even when I was poly and SINGLE, than the fact that I was developing feelings for her.
She's been struggling with her marriage for a long time and she seemed to think that I was advocating one of two things - poly or divorce - when I was simply advocating for her to do what was right by her own developing standards. For years, she stayed with her husband.
Several weeks ago, and after I got myself to believe that holding those feelings for so long was unhealthy for me, she divorced of her own free will. After becoming limerent toward my best friend who is mono.
I have to wonder, partially arrogantly and partially just to ponder how domino effects happen... Had I been visibly "single" at that time... Had I been less of a leap from her valued "traditional" relationship, may that have happened sooner? Might we have become involved?
But I don't strictly REGRET my decision. I just wonder.
Connection is the path to passion. Passion is not the path to connection.