Hey all, I've sat in judgment of several questions in this sub, now it's my turn to be judged. 

Story: My wife and I are monogamous. A few years ago, we joined an IRL community that meets on Sundays. We're not religious but we didn't have any friends after moving from the town where we met, and we found a non-religious community that was welcoming. A TON of the people in the community are polyamorous. We'd never been exposed to that. At the time, we knew that wasn't for us - it didn't bother us, but we had too many years of thinking that serious relationships are only monogamous for us just to overcome decades of living a certain way that fast. We did talk a lot with each other about it, which led to us being more open with each other about crushes (a good thing, IMO). 

I struck up a friendship on Facebook with a friend of my best friend. We started off just sending memes and chatting about news and other stuff. She said we should get dinner sometime. Now's a great time for me to say that after years of being completely monogamous, I am Naive. As. Hell. I didn't read any romantic overtones into her saying that, so my response was basically "Sure! Next time you're in town, we can hang!" She let me know a couple months later that she was going to be in town, and asked me to dinner. I said "Sure! Can \[mutual friend\], my wife, and my kid come too? We all like \[the restaurant she wanted to go to\]!" She said that was totally okay. 

After the dinner, she messaged and asked if we were polyamorous, and put forward that she was attracted to me. I showed it to my wife immediately, and she helped me draft a response: "Flirting isn't illegal, but it won't go anywhere with me, and we're really not poly."

Well, she did take us at our word and kept flirting. I'd keep telling my wife, and she just said "I'd rather you not flirt back, but if it makes you feel good that she's flirting, I'm okay with it." I told this lady as much, and for a few more months, it kept up that way. I checked in with my wife, and that's when my wife said "Do you want to flirt back?" I said "I have to admit, I really like her, and the flirting is pretty fun." My wife gave the go-ahead, and even offered to help me flirt if I wasn't sure what to say. I was over the moon. 

There's no question that I was the asshole at this point: Having zero experience flirting in over a decade, I took it over the line into outright sexting. No pics, but me and the lady I was flirting with had covered pretty much all the ground in texts. There was a point at which I realized I'd fucked up, and came clean to my wife about it on my own. She was really, really, rightfully pissed. I took what was coming, stayed in my doghouse, and worked to make it up to my wife. Wife told me that she felt partially responsible for greenlighting everything, but not staying as involved as she felt she could have, and that I shouldn't just dump my flirt. Wife said we could keep in contact, but to keep it strictly G-rated. 

That lasted all of two days before the lady I was flirting with made a sexual comment about me being sensitive to one of her phobias, saying "The fact that you care about this stuff really turns me on." Remembering the doghouse, I immediately blew the whistle and told my wife, and she shut everything down. I went with it, remembering my fuckups from before. Before I cut communications, I'd told the lady I was flirting with that I hoped we could stay friends, that there was a lot I thought we had in common, platonically, and that even though she made a clear mistake, I still thought we should be friends. Her response was "you shouldn't stay friends with me." Normally, I'd leave it at that, but I knew that the lady I'd been flirting with had a history of depression and found the darkness a little too easily at times. I told her I wasn't going to just abandon her. 

Then, my wife said she was just done with all this drama, and had cut communications, and that she really wanted me to do the same. Again, remembering my fuckups, I didn't feel like I was in a position to argue, so I cut ties...but I really wonder if that was an asshole move after I'd told her everything I did about not abandoning her. So, my judges, AITA for going back on my word?  


TL;DR - Married, monogamous dude gets permission from wife to flirt, it goes too far, wife shuts it down, flirtee crosses a line, dude basically promises flirtee not to abandon her, circumstances prevail and dude breaks promise, and now wonders if he ITA. 