When non-monogamy hurts

Let me start by saying I’ve always been a monogamist. I was married for over twenty years before my wife and I divorced. Last year I met someone I’ll call Lily. Lily and her girlfriend had been together for over 10 years. They had lived together briefly before Lily’s partner moved to another city, yet they were still maintaining their status as partners. I got the feeling that Lily was not very happy in this relationship, that it was unfulfilling, the two of them were rarely if ever intimate, she was very lonely, and from what I observed, her partner took advantage of her by doing things like dumping her dogs on her to take care of for the weekend.
It didn’t take long before Lily and I acknowledged our mutual attraction, and after weeks of flirtation and some intense make-out sessions, we ended up sleeping together a few times. Lily found out during this time that her girlfriend *may* have been cheating on her (although I never knew this for sure). Lily was very upset, even though she was doing the same thing. By all observation, I thought their relationship was doomed. I went full-throttle into pursuing something with Lily. By all regards, Lily is perfect for me — physically and intellectually — and we have the best sexual chemistry ever.
As time has gone on, though, Lily and her girlfriend have stayed together. She sent me a link to an article on polyamory at one point, and I think she is truly in love with both me and her partner. She has told me she loves me, and though she tried to play it off as something she says to her friends, her actions say otherwise. As far as I know, the partner doesn’t know Lily and I have been physical, although she knows we spend a lot of time together — movies, dinner, TV, etc. I’ve met the girlfriend several times (very awkward) and had dinner with both of them a few times. I think the girlfriend is beginning to suspect there is something going on. Lily says she has made surprise visits to Lily’s apartment, and I think she’s hoping to catch Lily and me together.
Lily has not actually said she wants to be anything but a FWB with me. But as much time as we’ve spent together, I’ve fallen in love with her. I couldn’t help it. If I had known she and her partner were never going to split up I would NEVER have gotten involved with her. For now, I think Lily is comfortable with the situation. I’ve seriously thought of how I would feel about being in a polyamorous relationship (although I could never be in a triad as I am not the least bit attracted to her partner). I love Lily to the point I would almost consider such an arrangement, but only if all parties agreed to it. And I have no idea if the girlfriend would be open to it or not. But then I have to wonder what the future would be for Lily and me. I can’t see myself staying in that kind of situation long-term.
I’m wondering if I just need to break things off with Lily, painful as it would be. I don’t have any experience with polyamory, and I just don’t think I’m cut out for it. What’s your advice?

This is quite a dilemma to be faced with and you really do have my sympathies.

It looks like from the start you weren’t very honest with yourself. You’ve known yourself to be monogamous and it doesn’t sound like you have any genuine interest in polyamory and, as you said, you probably would not have got involved with her if her and her partner weren’t going through such a hard time. One thing I want to highlight in this letter though for you and anyone who reads this is that, if Lily had better boundaries in place and was actually polyamorous, she probably would have also not let this progress this far either.

Whatever is going on with her and her partner, I find it extremely odd that you would know so much without also having a clear conversation about what your relationship is meant to become. It makes me feel like Lily was using you from the start. You provided her the emotional support she could not find in her partner and also physical fun. She gained your sympathy by telling you about how difficult their relationship was going, letting you in on more information that wasn’t really your business to know, and kept you going on and on, all this time.

Then she sends you a link about polyamory and, in credit to Lily, sometimes this is how people discover polyamory. Monogamy is a cultural given and a lot of people who can’t do monogamy find this out the hard way. I’m not going to say that someone who cheats is incapable of being polyamorous because there are so many reasons people cheat, but what concerns me about what Lily’s doing is not the suggestion that she’s been dishonest with her partner but that she involved you so much in this process and really has never made it clear to you where you lie.

If her partner is making surprise visits to Lily’s apartment, it’s safe to say that Lily is cheating actively and involving you in that. And the fact that she’s comfortable with that is the biggest red flag here for me. She hasn’t bothered to ask you what you want out of this. Does she know that you came out of a 20 year marriage? I would expect a person like that to probably want monogamy and my suspicion is that Lily knows that’s what you want but, rather than being honest with you, she’s going to keep you for as long as you’re willing to entertain her.

Likewise, she’ll keep her partner stringing along for as long as she can. Ask yourself if this is a person you would want to date monogamously or polyamorously. She has proven to you on multiple occasions that she is primarily interested in getting what she wants. Whether you are dating one or more people, you need people in your life who care about your wellbeing and will not be willing to sacrifice your needs for theirs.

I don’t think this is a situation where you should try polyamory because I don’t think this is a situation where you should even try monogamy. I think you should find someone who isn’t already in another relationship. If Lily had made some type of commitment to speaking to her girlfriend about polyamory, of giving you a timeline for when she would introduce the concept, or even trying to make it clear to you what you mean to her and where she sees your relationship going… then maybe I would be more optimistic. Sometimes this is how people discover they aren’t cut out for monogamy.

But, the fact that, as you said, Lily is comfortable in a situation where her partner doesn’t trust her, where she’s potentially cheating on her partner, and she’s happy to keep you along even when you feel uncomfortable… I don’t think this is really a situation you should engage in at all. You could try giving Lily your own time limit to discuss this with her girlfriend because you do not wish to stick around but… if you are not sure you want this kind of situation long-term, even if it’s not cheating… It might be best to cut your losses and find someone else.

I hope this helps and good luck!

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