The Courage To Have The Most Difficult Conversation With Your Best Friend

Leigh Lim
11 min readDec 3, 2021
Photo by: Paul Clifford

I’m constantly amazed on how there are times when things just fall into place. A seemingly inane example is the fact that I was able to discover ‘Saving Face’ (Alice Wu’s 2004 romantic comedy masterpiece) just at a time when I was ready to watch such a film. It had everything I was looking for (funny, layered writing, and well cast actors) and an extra bonus that helped me gain an additional worldview. Prior to watching the film, I paid little attention to (and at times even skipped) scenes with romantic connections between two women.

This led me into a rabbit-hole of queer content (which I consumed as I put together my write-up for the film). I learned a lot of relationships that began between friends. At times even best friends. Women mentioning the epiphany of one day realising that they’ve fallen for their best friend (or a ‘practising heterosexual’ falling for a close lesbian friend). I let myself wonder what would it be like if I ended up in a world where Sapphic relationships are the majority. Will I be part of the minority? Or would I be more open to marry a woman both because it is safer (and as a result I’ll be among the majority) and there are more chances to finding a life partner (since the dating pool is more significant)?

I would like to say that I’ve been good at following my intuition through the years, but there are times that something else would take precedence. One such epiphany hit me as I was reading through the transcript of episode 41 of ‘We Can Do Hard Things’. My brain somehow wouldn’t let me keep reading after I got to the point when a listener (Jenny) was sharing about her shock (because neither of them had never been with a woman) after hearing a female friend (who is married to a man) confess falling for her. After trying to figure out what was going on, I eventually traced it to the fourth item on what I put together to give to someone who’s keen on ‘assisting’ in finding my life partner.

Apparently, I have to have a conversation with someone who I no longer am in constant contact with. Lets call her ‘Estranged Old Friend’. If not for the knowledge that I best keep my distance from her (due to an experience about 10 years ago when I learned that we were at different paths — — mostly that I was on the ‘personal growth’ train…and she was…not even close to it), I would say that she would be my oldest and closest friend. The link to item #4 was a series of conversations we had that I (now) realised that I could have been more supportive. Because of having viewed ‘Saving Face’, fallen down a rabbit-hole of queer content, as well as taking the time to figure out why the film resonated with me…I felt I ‘leveled-up’ my empathy level.

The biggest epiphany was the realisation that ‘Estranged Old Friend’ might not just want to have a conversation about queerness, but also wanting to convey her interest in being more than a friend. Of course I honed in on the former, regretting that I wasn’t there for her when she needed me to. The first instance happened sometime during our adolescence. I was at her house a lot as it was a safe space to be while I was going through mine. The frequency of my visits eventually caught the interest of my mother who one day asked as I stepped through the front door if there was something happening between us.

I was really reluctant to reach out as the last time I spoke to ‘Estranged Old Friend’ (at least to my recollection), there was significant tension. I understand that it’s probably me being a ‘fixer’ and seeing all these things that she could improve in her life. I’m not sure how many ‘here’s how you can improve’ I presented to her, but based on my personality, I would guess there would be at least a couple. So the conversation with my brain went like this:

Fearful Me: No…don’t make me call her.

Personal Growth Brain: You know you have to do this. I’ve already proven that it is something that you need to walk through. I know it might be something that could cause you pain…but there is growth behind that.

Fiery Me: Says you! She already proved that she’s not someone I would want to be around. Do you even remember the conversations we’ve had?

Emphatic Brain: Wouldn’t you want someone to extend a little grace if you’re being difficult?

Fiery Me: Aggggghhhh! Okay! Okay! I’ll do it. See!? I’m looking up her old number. I bet it won’t even work as the last time I rang…she didn’t pick up.

Personal Growth Brain: The only thing you need to do is to make the call. Aren’t able to get through her mobile? Try the landline. Then if it doesn’t work…send an email to ask if she’d be okay to catching up via a secure messenger.

One of the things I’ve learned is when there is something that I feel I should take action on, now is the time. Because whenever I’d spring to action as soon as I could (even within that hour of the epiphany), I would discover that it would be the optimal time. Proof? Well, after I prepped my notes (of course talking points are important for the kind of brain I have: one that tends to go on tangents), I tapped in her number and after checking that mine would be displayed (I usually would block my number in case the person I’m calling has changed their number or if I mis-dialled) and after barely two rings, she picked up. How cool is that!?

Now, we did hit a bit of a bump in the whole phone call situation as she later mentioned that she lived where reception was bad. After the third ‘hello’ confirming that she couldn’t really hear me properly, I ended the call and sent her an SMS. I used that one word that we refer to each other. The word that represents how we basically adopted each other. When I read her response, it was confirmation why for a period of time she was my best friend. The explanation for the reason why, at one point, she told me I was her ‘soulmate’.

(Okay…I know if you’re rereading this…the ‘soulmate’ comment sounds like a love declaration. It was in a way…but more of a proof of friendship. How deep our connection was. More similarly to what Ashley McKinney and Justine Gendron shared during their appearance in an episode of ‘Best Forevers’. Though we did not declare how much our friendship means to us as publicly as they did.)

I’m guessing that it was more of hearing my voice (but not being sure) than my one word SMS. But we were able to jump to a more secure messenger. She didn’t have it, but didn’t have any issues creating a new handle so we could continue our conversation. After I apologised (I was thinking of those good times!) it took awhile for me to reach out, she mentioned that she wasn’t able to contact me as she lost all of her contacts as she changed phones. Of course, my ‘fixer self’ wanted to ask if she now has an offline database of her contacts and other important notes. I’d like to think that it was a result of me leveling-up that I did not ask her this.

Since I met most of her family and she also basically has been taken in as ‘adopted’, we were able to catch up on what had been happening. I shared the little things in my life (that is only possible with someone who has that kind of connection) and the years just melted away. However, things did take quite a negative turn: When I gave her a snapshot of my journey (thanks in part to ‘Saving Face’) on being able to find more empathy towards those who identify as queer and expressed regret that I didn’t probe more when she asked me about what I thought about her dreaming about one of our other female friends.

I’m not going to share the detail of the dream. Because the important thing in that scenario is I just waved it off. Years later, thinking about that moment, I’m wishing I asked what ‘Estranged Old Friend’ thought the dream meant to her. Now, as a middle-aged-woman, I no longer put importance on what dreams mean as I know that it’s the brain cleaning itself (to stave off and even prevent Alzheimer’s disease) and I just happen to catch a bit of the ‘memory sludge’ that was flowing through as it was happening. That’s the practical side of it, explaining why the dream happened. But there’s another side of the actual person linking something to the dream. This is what I wanted to check.

Since ‘Estranged Old Friend’ is only interested in the ‘now’ (any disagreements between us usually stemmed with me asking about something that happened and her being annoyed that I didn’t bring it up right then and there) which made me wonder if she’s actually an extrovert. I already know that we’re both Fiery Alphas (though I have not been regularly at the receiving end of this…I had witnessed her getting washed over by emotion and it would take awhile before she could be objective about something that happened), but the link between wanting to focus too much on the ‘now’ and not really interested in the past (to the point that it’s difficult for her to remember past conversations) is something that is very much a trait of an extrovert.

I had mistakenly assumed that she was an introvert (like me) and that was the reason we got along so well. It probably took me another realisation that extroverts could be book lovers too. Now I think it’s more that we are both quiet people. Her inability to understand that I was going through my own personal growth (because sometimes it is not too late to act or apologise for something that happened years and years ago) was a big contributor on our conversation going south. My messages were focused on clarifying what I was saying, but then she was hearing me trying to judge her rather than checking that I just wanted to find out if I missed out on something. I initially thought that it was because we weren’t having a voice chat and rather trading typed messages. Somehow I’m convinced that it’ll still end up in the same place: with both of us (or at least me) knowing that time apart is the best thing. Want to talk to an extrovert about the past? Wait for her to bring it up again, rather than hoping she would be able to recall something she said previously.

The point when I knew that we might never be able to walk it back was her asking me if she looked like someone who was into women (which was a shock to hear because as ‘Saving Face’ reminded me: there is no such ‘look’), and how pissed she was that I would assume that. It was bad. I was saying one thing (“Could I have been a better friend when you asked me that question?”) and she was hearing another (“Just admit that you’re a lesbian!”). Unfortunately, the jury is still out whether we would recover. I had taken a bit of time to let my feelings (I was really pissed off that she would think that I was trying to ‘out her’ or overpower her with the information I had), but I eventually managed to find a way to pivot and see things from her side. I was really ready to purge everything that had links to her (like my favourite pink hoodie) and surprisingly found myself softening as I was rereading our earlier conversation to make notes before it completely self-deleted. Being able to find a perspective that would allow for me to have more empathy towards her was helpful in crafting my responses.

Apparently, I took too long and it seems like her rage had been too much that it drove her to delete the secure messenger (I’m not going to name it — — because it might come across as me being compensated to mention it…or that I have other monetary interests in the app). When I hadn’t received a reply in 6 hours. I sent over an SMS thanking her for waiting for my answers and saying that I received her responses and sent 19 in reply. She wasn’t interested in my offer of re-sending those 19 messages as she doesn’t have anything more to say to me. Of course, I desperately wanted to say that the specific lot of messages would likely make things right again between us. That it was me seeing what was happening and making an effort to turn things around.

Will I get a chance to share those two podcast episodes that were included in those 19? The episode of ‘The Cutaways’ with Ashley and Justine discussing ‘Saving Face’ and basically just being so cheeky with each other that it could be mistaken that they were in a relationship. But after listening to their episode of ‘Best Forevers’, I now know that Justine was likely messing with the listeners (but maybe just Ashley?) when she stated that they were married. I’m quite positive that ‘Estranged Old Friend’ would have loved both episodes (maybe even laughing in the same parts as I did) as it was an example of a friendship that was extremely close.

It really doesn’t matter if indications were that ‘Estranged Old Friend’ fell for me at one point and she was attempting to take the steps (like reaching out for my hand and intertwining her fingers with mine long enough to make me slightly uncomfortable and wonder what was happening or later commenting that if she were a guy…she would pursue me) of finding out if I was possibly open to considering if there was an ‘us’. Women Loving Women (WLW) who identify as a lesbian, pansexual, or bisexual would probably be able to cite an incident in their relationship timelines where either they made that hand-holding move (the intertwined fingers) or was pursued by a woman who used that ‘move’ on them. What was important was her truth. If ‘Estranged Old Friend’ doesn’t feel like there was anything to it, then that’s the end of it. That was the point of me reaching out and asking if there was anything I could have done to support her more.

Maybe I wouldn’t have been open to her advances (if it was of that nature), but at least we could have had the conversation. At that time, it wouldn’t have occurred to me to pursue a relationship with a woman as I was quite content with the connections I’ve made with men. 2021 is a different story as I would think that I’m at a point where I’d be focused on getting the person inside before the one the rest of the world sees (I would think it would include both gender presentation and gender identity). Consent really wasn’t in the discussion rotation in popular culture those days, and even if it was…I doubt ‘Estranged Old Friend’ would ask if she could hold my hand. I bet it would have been ‘Estranged Old Friend’ just holding my hand assuming that it was okay with me since it also happened (she later tells me) with the other female friends she had during that period.

Whatever it turns out to be, I hope you could go at it with more gusto than I did. In the words of film editor Ashley McKinney: we have to give people a chance to be either the good guy or the bad guy. Though you probably know that if your closet friend is going to drop your friendship just because you wouldn’t be a godmother to her son or invest in her startup, the friendship is something you might need to either downgrade or walk away from. Until you ask, you would never really know. Push through feeling ‘silly’ about asking whatever you feel like you need to and you might be facing a whole different level to your friendship. You might even pave the way for your current ‘bestie’ to feel safe ask you something she’s been wanting to for ages.

For a boatload of quotes (and some of my thoughts) about friendships, you can dive in here.

PS: What were the difficult questions you needed to bring up in the course of your friendships? (Are there still questions you still have yet to ask?)

Drop me a line here or comment below! :)

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