Alright this is something I have avoided putting into words for a while.
In 2024, I frequented this coffee shop on a weekly basis. I had begun to get familiar with some of the people that worked there. One day in late autumn, I walked in and someone I had never seen before was behind the counter. She is overwhelmingly beautiful. I remember looking at her for the first time. It was a shock to my entire system. We will call her M.
Fast forward a few months. I got to know her name and we established the unremarkable rapport that so often passes between a service worker and a regular customer. I realized that a convenient opportunity to ask her out was not going to spontaneously appear. I didn't want to ask her out while she was working but I was at a loss for what to do.
One day M happened to be sitting at a table outside on her break. I decided then and there to ask her if she wanted to hang out some time. She said yes. But she qualified it saying that I should know she was seeing someone. It ended up never materializing. I texted her a few times about doing something, but for one reason or another... nada.
Fast forward a couple more months and I have become good friends and climbing partners with a coworker of hers. More and more I am invited to different events and outings where this woman is going to be in attendance.
As hard as I try to get over it, move on in my head, I cannot shake the strong feeling of attraction I have toward this person. Eventually we become somewhat more close as friends. We begin to hang out to study just the two of us sometimes. As time passes, we begin to talk about more meaningful life things. Deeper conversations.
It's important to note that at this point I have met her boyfriend. He seems like a good enough dude. He's nice to me, which is remarkable considering he almost certainly knew I had shown some mild interest in his partner. He's also good looking and kind of a freak athlete. L.
Ok so, now it's 2026. Some things have changed. I saw someone for a short period of time, but it ended after a while. One day, after I invited M and her partner to hang out with me and another friend of ours, she tells me that she and her boyfriend are broken up. Later, at one of our study sessions she gives me the details. Turns out he was kind of a dick. L.
In the interim, we both got accepted to grad programs. Me here in town at the local university. M got into her dream program in California. I am very happy for her. I am devastated for myself.
I think it is also important at this point to acknowledge that while I still am very attracted to her, M has not been the easiest person to be friends with.
She's very nice, very easy to talk to. But she is difficult to make plans with. She can be flakey. Sometimes she'll invite me to go do something on a particular day, but then when the day comes I don't hear from her until last minute, to cancel. When she's in front of me, she puts her undivided attention on me, and our conversations are very engaging. But at other times she seems very aloof.
Our mutual friends, unaware of how I first asked her out, tease her at times that on a daily basis young men walk into the shop and are bewitched by her. She does not deny it. She does not so much as look at me while she laughs and brushes off this insinuation.
It did not take me long to realize that it would be foolish to allow my own happiness to hinge on anything that had to do with her, since she was, in the ways I have described, unpredictable and at times not so reliable either.
Realizing these things about M has done very little to diminish the deep feelings I have for her. At times I wish I could just let these feelings go, and leave her be, and let her leave me be, in turn. But I cannot. There are nights where I am sleepless tormented by the picture of her smile in my head. She is absolutely radiant. And every time I see her in person, I am taken aback at how poorly my imagination captures the reality of her beauty.
So, it's summer soon. She leaves in August. I'll be staying. She's single. I'm single. But it's not the same as it was before.
When I asked her out the first time, I had nothing to lose. But now she is my friend. I care about her and her feelings. I care what she thinks about me. I doubt very much that she feels anything for me that approximates what I feel for her. And if I endeavor to ask her out on a date at this juncture, there will be no ambiguity as to what I want. Not just friendship. More. If she rejects me, I would be more than happy to move past it, and allow our friendship to continue as it always has. But will she?
I do not know what to do. I went to bed last night convinced that the right thing to do was to ask her out and be done with it. Be what it may.
This morning I woke up once again uncertain. Am I a fool? Surely she knows that the first time I asked her out, over one year ago, that I was doing so because I was attracted to her. Surely she hasn't forgotten. What does it mean that neither of us, in the many times we have hung out, have ever acknowledged that day?
Part of me feels as though, since one way or the other she will be gone in no time at all, that there is nothing to lose. Another part of me feels as though every bit of this is folly.
I am in emotional pain at the weight of this feeling on my heart. In those moments when I have the good fortune to see her face and hear her voice, I spend the rest of that day in a state of total elevation. I walk down the street with smile on my face that I cannot suppress. But at times, when I feel she doesn't really think about me at all, I feel totally hollow. I fear how it will feel when she is finally gone. And I fear how it will hurt if I allow myself to believe there is a chance for us to share a special connection, even for this short while, and it turns out there is not.
Help me. Tell me whether or not to ask her on a date.