Tldr: the title my friend Melanie previously said she had feelings for me and I strongly sense she still does Melanie is interested in ethical-non monogamy but her girlfriend is less so, I am also interested in ENM and would be okay dating her if she still dated her girlfriend I am planning Melanie’s secret birthday celebration with her girlfriend for next month which makes the timing a bit awkward. When is the right time to say something and is there anything I should consider to approach this with as much intentionality as possible?

Context:

I have started to feel strongly about my friend of two years, Melanie, but as the title says she met Josie 6 months ago-ish. They've been girlfriends for 3 months now. This is a bit of a long one so thanks for sticking with me hehe.

I met Melanie a couple of years ago and we became instant friends. After 4 months knowing each other, she told me she had feelings for me but I told her I didn't feel the same way. Thinking about why afterwards, I realised that even though I could imagine us having the most beautiful life together, I'm drawn to dominant women sexual attraction-wise, and our dynamic is moreso soft and sweet.

Also on my end, I struggled with understanding how intimacy works after a very comphet sex life, so I was still learning what queer dating could look and feel like. And within our friendship, there were some communication issues because she didn't express her boundaries/preferences enough, so I was often second guessing what she actually wanted - I needed to learn how to give feedback and communicate better too.

After 8 months knowing each other, I realised she still wanted to pursue something with me when we met for lunch one time because she was being very romantic: bringing flowers for me, turning the conversation back to our dating/sex lives several times, paying for the meal, reaching for my hand when we left… So it showed me she was still hoping for something.

After this she had two short relationships. In the first, they broke up due to compatibilty issies around Melanie not wanting marriage and kids and Mel wanting to explore ethical non-monogamy (ENM). This showed me that me and Mel are really aligned because I want to live the same way, and I sensed that she was hinting about being with me when we spoke about ENM (but that could be me reading into things). The second relationship was full of red flags so I advised her that it didn't sound healthy for her, and she broke up with them. Since then she's been saying she trusts me with her life because I've been there for her through difficult situations. in general, this has been the hardest year of both our lives so we have grown a lot closer by supporting each other.

Then 6 months ago, she met her current girlfriend Josie, and she is so amazing. Josie met Melanie on a dating app since she was ENM too. Josie broke up with her then girlfriend (fair enough, she was not a nice person) and was leaning towards being monogamous after meeting Melanie. But Melanie still wanted to pursue ENM, so the boundary they settled on is that only flirting is allowed with other people.

And now coming to a few weeks ago, I had to have a difficult conversation with Melanie because of an imbalance in the way we were showing up for each other. When we unpacked this, reconciled and set new boundaries, I felt so much closer to her and we were both happy about how safe we feel being honest with each other.

Since then it’s been wholesome vibes - she’s been making me feel appreciated, and I’ve spent a more time with her than ever before cooking together, introducing her to tv shows, unpacking life etc. She was super supportive of a misadventure I had last week when I was feeling frisky for the first time in a long time and was wondering whether to hook up with this random guy I met (sidenote: that whole mess was the final confirmation I needed that I am sapphic/a pansexual lesbian lol). I noticed after recounting that silly sexual encounter to her that she was looking at me a lil intensely and lustfully. I think her feelings for me might not have fully gone away because she’s been flirty with me a few times in the past months - she gives it away by giggling about how she’s such a flirt after, but I could be reading into it.

So I started to fall for her after that because I rethought our compatibility and realised that she is everything I could possibly hope for. Our values align so well, we already trust each other and want similar things for the future, we inspire each other so much... I already have a sensual attraction to her and I know the sexual attraction has been building because she has expressed frustrations about not being able to explore her dominant side with her girlfriend (she’s a switch like me yay :)

And we have come a long way from the communication issues that worried me 2 years ago. My only reservation is that our dynamic is warm and soft, but I always saw myself being most compatible with someone who also has a deeply dry/sarcastic sense of humour (because there would never a dull moment). I know that this isn’t a dealbreaker for my desire to be with Melanie though because I don’t believe in the idea of ‘the one’ or expect my partner to fulfill every single one of my needs/ desires - that’s what friendships are for or having more than one partner through ENM.

The ironic thing is that I’m secretly planning Melanie’s birthday event for next month with Josie. This process has made me appreciate Josie so much more, and she said the same for me because I rooted for their relationship when Melanie had doubts in the beginning. I would be okay with dating Melanie if she continued to date Josie (at least I think I would be. I’ve never been in a relationship before, let alone an ENM one, but I feel peaceful about this and know that our relationships to Melanie are completely distinct and she loves us in different ways).

I know Melanie would want to know how I feel, and she’d be miffed that I haven’t told her already. But the timing doesn’t feel right because my revelation might cause issues with Josie since she wants different things from ENM to Melanie - I know that this would happen regardless of the timing, but I don’t want to risk being a catalyst for a break up before her milestone birthday because Melanie is working through some issues in her relationship to Josie right now (nothing they can’t get past I believe). Also Josie has put a lot of money and effort into the birthday plans. So even though I desperately want to tell Melanie now, I think it's best to wait until next month. And also December is a difficult time for Melanie so that would be bad timing too

So I would appreciate any advice about the timing and if there is anything I should consider in order to approach this as intentionally as possible?

Thank you in advance!

[Just to confirm - Mel and I haven’t done anything outside of the boundaries that she has with her girlfriend.]

Also I recently introduced her to reddit so I hope she doesn’t see this haha