the harry met sally conundrum


Women, women, women. How often are we guilty of this: How long are we into a conversation with a cute guy, when we hear his last name for the first time and imagine how it sounds with our first name? How often do categorize in our heads the potential boyfriends apart from the “never ever will happen” friends?

So there’s an argument, and When Harry Met Sally is a good illustration of the argument. Can men and women be in long-term platonic relationships?

I do not have the best (long-term thinking) answer for that. But I know that most of my friendships have not been long-term, with men and women. And their degrees in closeness have varied at times. So, I do not seek to answer that question. I do seek to help us understand that how we women often categorize, daydream, and overanalyze is building unhealthy walls to really beneficial meaningful friendships with men.

They can happen. They might be ambiguous, but that’s part of the fun.

I am currently working on changing my brain tracks. I have one track that goes into Teen Girl Squad mode, that can be absolutely relentless and always dwelling on everything that could happen with a guy. But I have been developing a more mature, sober-minded track that challenges the TGS thoughts. I am seeking to just completely change my mind in this matter. I want to be good friends with guys and have absolutely no expectations. I think I am starting to reach a good place.

I am sorry, men. For a long time, I haven’t valued you as friends who should be valued. I was overcautious and sometimes a bit contemptuous.


This has been a year of emotional risk-taking for me. I have had to become friends with guys. And I don’t mean just surface-level awkward-side-hug friends. But I mean friends who spend a lot of time together and actually know each other. Friends who are there for each other. Friends who delight in being around each other. While balancing the tension of my own attractions and over analysis.

I am actually a natural when it comes to having guy friends. Maybe it’s because I grew up with three older brothers, have a wry sense of humor and am satisfied often with only talking about topical things. In college, almost all my friends were guys. But after college, some sort of shift happened. I did not keep up as well with my good guy friends, even if we saw each other regularly. Overtime, I started only seeing them in groups of friends. And at some points of time, I even refused to text any guy friends at all, unless there was a super particular reason.

On the surface, I looked like I was doing fine, and being friends with guys. But inside, I was dying from overanalyzing any act of intentionality. You know that feeling when you find someone interesting as a possible friend, but you’re scared to talk to them because you are afraid they may misread you? That was the story of my life. There were plenty of potential good guy friends in Virginia, but I gave them all nervous smiles and moved on. There were a slight few who I had been long-time friends with, but those were the only men I found safety with.

But then along comes seminary.


Seminary does not have many girls. And I could count the number of single girls in my class on maybe one hand. There have been a ton of guys around, and for part of my first semester, I ran away from pursuing good, solid friendships with them. My slowness of being friends was probably not a completely negative thing however.

It gave me time to find a few friends who I feel safe with and who I trust. I feel very grateful that I can name a few guys this is true of.

In my first semester of seminary, I wrote a post called Boys and Girls and Proximity. I read it today and laughed at myself. I don’t think I necessarily stated anything completely untrue, but it is hilarious how well it captured my shock of the reality that I have to be friends with guys in seminary.

My attitude toward friendships (my heart) has completely changed since writing that post. That post was about being friends, but it was also about dating. And this post is not about dating. Well, not so much.

Every time I’d become friends with a guy in the past, I have questioned it. I have wondered if there was potential for dating. If they paid extra attention to me and we spent one-on-one time together, I would automatically assume they like me. Now, I have learned to just stop at friends. Dating is fun, too. I am not against dating friends. But I have learned to stop thinking about guys in that way every time we would do something intentional together. It just stops at friends.


Intentionality. This has been a long road for me and it has not quite ended, yet. But I have learned to be intentional with guys and not feel weird about it.  When they are intentional with me, I no longer think they are “testing the waters.” I simply believe they enjoy my friendship and that is all I need to know. In the past, the ambiguity has killed me. But I am learning to live in the ambiguity with intentionality.

I also find that a life of intentional friendships with different men is incredibly healthy. As a single woman, for a long time, I have missed out on what my brothers in Christ have had to offer me. Because I would freak out too quickly. But men bring something to the table besides being a possible significant other. They bring a part of humanity that I have been missing out on. Last semester, I was starting to become intentional friends with a few more guys, and I told my counselor how freakishly it scared me. She told me that it was a good thing. Friendships with men are more than just practice with my future husband. Assuming that I may be single for a long time, they are an essential facet of my humanity. I need guy friends to be refreshed in ways I cannot be refreshed by my girl friends.


People will always make assumptions.

If I am out with a guy in public (just the two of us), people always jump to the conclusion that we are at least dating.

I am learning that it is counter-cultural to be friends with guys.

With one guy friend, at least two times we have been paying for food, the cashier would ask if our purchases are together. I get why they ask this. But if I put the grocery bar down between our purchases, that is a pretty good indicator. It’s just something that men and women who are friends have got to be used to.

I watch the Disney channel all the time at work, and I am not ashamed to admit I enjoy the shows in a surface-level amusement. One show, Austin & Ally, has a guy-girl friendship and there is always a tension between them. On one episode, Ally loses her diary. When Austin finds her diary, he freaks out when he reads a description of a boy she’s crushing on. He starts acting weird around her. When things get resolved at the end of the episode Ally asks Austin why he acted so weird when he thought she liked him. Was she that repulsive? That gross?

I keep this in mind with my guy friends. I am trying not to act weird with cashiers. I could just imagine me saying “Oh no no! We are not dating! HAHAHHA. Gross.” Something out of some quirky sitcom.

Noooooooo. I should stop that. Because with any one of my guy friends, I am actually flattered that people think we’re dating. I never quite express it that way to them, but it’s true. They are really good people. Just because I am “just friends” with someone does not mean I want to “friend zone” them. I want to delight in their friendships and I do not want to bust their egos. This is not to say I want to fill their egos, but I want to encourage them, honor them, respect them, and build them up in Christ. “Friend zoning” is not honoring who they are and our differences in gender.


All of this is hard. Especially in the Christian culture we live in. A lot of books I have read make it seem like in the Church that guys belong to guys and girls belong to girls. Certainly, there are things I would talk to my girl friends about which I would nevvvver say to my guy friends. But this doesn’t mean we should separate ourselves into these different clubs. And this doesn’t mean that when we acquire significant others, we should suddenly ignore each other. Dynamics will change between opposite sex friends, but just being a friend with someone does not mean they are a “close call” for an affair. Boundaries are always essential.

Setting appropriate boundaries, though, does not mean putting up walls around our hearts.

It’s vulnerable to take the risk. I mean, it’s really hard for me to open up. But I know it’s good and healthy to be available to them, to share aspects of my femininity with them appropriately. To love them as brothers in the Kingdom. To practice being the Church with the opposite gender.

And it’s fun. Just in the past week, I have had hard and good conversations, I have appropriately practiced vulnerability, I have shared meals, I have gone clothes shopping, I went to the City Museum with only guys. A group of us even read the weirdest fairy tale out loud in British and German accents. And it’s always nice to go walking at night, and as a female who sadly cannot safely do that herself, it’s always great to bring a guy friend along. To walk, and talk  enjoying each other, the time and the company we give each other.

It is worth embracing the ambiguity of guy-girl friendships. It is worth not knowing if it will continue or desist, just like that movie struggles to answer.


2 thoughts on “the harry met sally conundrum

  1. Good words, describing this tricky landscape, with its potential pitfalls and joys. In somewhat related note, I once invited a friend, who I admit I was interested in, to a hayride. I told her It would be a “platonic hayride.” Since then, I have always thought that would make a great band name 🙂

  2. Thanks, Neil, for the positive feedback. That would be fun band name and I also find it funny how we use the word platonic as some kind of defense mechanism sometimes when we just wanna spend time with someone (and often when there is interest!). I am more inclined to overuse friend language when I find more ambiguity with feelings toward people. But at the same time, letting others know that there is safety there is never a bad thing!! 🙂 There is a tension..

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