My gut response?
Should I try to talk to my friend first, or his wife first?
Husband. He's your friend first, talk to him first. UBER-respectful.
Make clear you will NOT do anything, or even let her KNOW of your crush. Because you value his friendship, and hers and you aren't having prurient interests but struggling to pay a compliment and ask if there's interest.
You've always been monogamous. You've never tried poly. but you would really, really be interested in trying to date this particular woman in this particular poly setup if all is good because you admire their communication ability and admire their skills and you feel good and safe with them, good enough to share this... even though inside you wobbly.
So even if it comes to NOTHING... take it in the spirit offered, that you hold them and their rship in highest esteem and aspire to something like it someday even if there's no spark here.
Should I get them both together and bring it up at the same time?
Hubby (your friend first). He can choose to let her in on it or not in his own time, and then initiate negotiation for just a trio talk, nothing more. Everyone respected and on the level. Just trying it on in their heads in a talk and no more.
Nobody ever DIED from going uber slow and uber respectful.
And if y'all decide not to go there you can at least enjoy friend intimacy and a titillating talk.
If I think my friend might have a problem with it, should I suck it up and leave them alone?
Depends. That's your call, you know the details there. Maybe you just want to put out there low key.
That you admire what they have going on. You wish you could try that one. Does he have suggestion for how to approach in safe way?
Take the temperature there. Maybe he's gonna reveal they crushie on YOU for all you know. Or maybe you pick up that there's no spark there, still friends, just no magic. Still happy to help guide.
But then spit it out. Maybe it never occured to them... but hey now that you bring it up... hrm.
If friend has prob? I'd suck it up. Apologize for rocking boat, make ammends for even bringing it up.
There's plenty fish in sea, man. Don't need to wreck a friendship with drama. Esp if it isn't one you want to risk losing.
What kinds of issues can I expect to run into that might surprise a usually mono person?
Sigh. IME, it was from my being the overlappy poly. Dating some open minded mono's and sorta another young poly. Overall it went well. In hindsight I am amazed this well for the age!
But I came across surprises -- like one relationship that got all huffy we weren't lovers. Like how come HE gets to be your lover and not me?! And I was offended because I'm not a candy bar -- everyone gets a piece? The rship needed to see if it would grow to there, you don't just get there because I'm there with another! (this one broke off fast)
Then I was surprised at tender spots. I was clear I was not exclusive, I was clear I was honest, I swapped names and numbers, I thought I was being as transparent as I could be and my second guy threw me for a loop. Because once we became loverly he found himself disturbed at the idea of my being loverly with #1. Like it BUGGED him -- he wanted to know but didn't want to know what the spacing was between him and other. Did I wait a day? An hour? Before having sex again?
I didn't think to talk this out, and neither did he and we were both surprised at it being so tender. We broke up and were good exes as friends and then his next GF wigged at me still being in his life as an ex-now-friend. I checked out to make his life easier and give space. He was annoyed by me doing that and annoyed with the GF, because he thought being good exes was a GOOD thing but... later when they broke up he called me me to thank me. Even as friends I kept putting his needs on up there with friend respect and well, she was an ex too now. Only a huffy broken one rather than a friend one. What kind of ex do you aspire to be?
I'd also be cautious of this in your case.... is it REALLY her? You sure your crushie isn't because your exposure to a poly pool of people is so limited? How big is your in real life poly pool? And are you actually crushie on her for HER or just because of the IDEA and pinning the ideas on to her as the handy holder? (I'm not sure I explain that well)
Another friend went thru a mega breakup with her V. She was the hinge. Because the quad ended because one male died in accident. They grew close in V for a time in the intense mourning (natural enough) and she thought it was permanent but then the arms of the V changed in their personal growth later. So it was a divorce of the "V" config commitment even though she and her DH arm were still married. (legal) It took flak. And she was STUNNED at the lack of support -- from her own DH even!
I told her too "I am so sorry. Had this been your legal marriage, people would be outpouring in support, I'm so sorry, divorce sucks, etc. But because this was a V marriage thing you are getting the SHUN. The "Whaddaya expect? You went looking for it" crap rather than comfort."
So if it ends -- not even if it goes SOUR and ends but just ends because the season is over? Are you prepared to mourn solo? Because you break up with the exes so can't mourn there necessarily with them. Will you have community support? Being afraid of the end is no reason not to relationship, but go in with eyes OPEN, ykwim?
Another poly newb friend had NO idea -- just jumping into the new adventure with wife. And he sometimes seems overwhelmed with the metamour management. Are YOU prepared for that? What if your loves have others, or if YOU find other? How will this impact the trio there and how will you handle? And do read up on poly math
Some monos I meet aren't even aware that there's at least 5 foundation rship in a 2 person config.
- me in relation myself as part of a couple. (as opposed to me to myself as a footloose single who answers to nobody but ME. I am different as a single -- my talk, my walk, ykwim?)
- me to him in couple
- him to him in couple
- him to me in couple
- us to us -- the couple as a unit, a team.
- (ghost layer that may or may not ever come to pass but needs talking about: Us to us if we become exes because we'd like to be good ones)
So they seem blindsided by poly math. My friend was boggled that when they opened up, he had to deal with his newbie nervy at dating AND deal with his wife being alternately depressed/delighted because her experiments weren't going as hot initially. They kinda had to shore up their foundation 5 some to be able to carry on.
Just streaming thoughts in no particular order for you to consider.