By Rachel Turner
April 28, 2025

I thought it was just going to be a simple dinner with some friends, but it ended up being one of those nights that left me questioning everything. My guy friend, let’s call him Jake, invited me to dinner, and I thought it would be nice to catch up with everyone. He even let me choose the restaurant, which I thought was a sweet gesture since we usually just pick somewhere on a whim. I was excited—just a group of friends, some good food, and a night of laughter.

But it wasn’t the night I expected.

As the evening unfolded, it quickly became clear that the “group dinner” was no longer the plan. Jake and I arrived at the restaurant first, and everyone else canceled last minute. So, it was just the two of us sitting across from each other, awkwardly trying to make the best of it. To be honest, at first, it wasn’t that bad. We chatted like we always do, just catching up and talking about random stuff. The conversation flowed easily, and for a while, I was glad it was just us. It felt like old times—no pressure, no expectations. But then, something shifted.

Out of nowhere, Jake started talking about how he wasn’t happy in his relationship. He told me how he was feeling stuck, how he wanted to date other girls. It felt so out of left field. I mean, he has a girlfriend—someone I know pretty well—and I couldn’t understand where this was coming from. He didn’t just say it once. He kept bringing it up, talking about how he didn’t feel fulfilled and how he didn’t know what to do about it. It was like he was waiting for me to give him some kind of comfort or reassurance.

I didn’t know how to respond. Here I was, trying to be a good friend, and suddenly, I was put in a position I wasn’t prepared for. So, I did what I always do—I tried to be the supportive, motherly friend. I said, “But don’t you have a girlfriend? Don’t you love her?” It felt like a logical question, but I also wasn’t sure if I should have said anything at all. It was clear that he wanted something from me, but I wasn’t sure what that something was.

Jake seemed to appreciate my words, but it didn’t change the fact that it felt so awkward. I didn’t want to be caught in the middle of something I didn’t feel equipped to handle. He had put me in a weird spot where I was now comforting him about feelings he had for someone else, and I felt like I was being asked to validate something that didn’t sit right with me. I mean, as a friend, I care about his happiness, but I also care about his relationship and the trust that comes with it. Was I supposed to just tell him it was okay to feel this way? Was I supposed to encourage him to figure things out with his girlfriend, or should I have just kept quiet?