Kiss and Tell: “For months, I wrote every text my friend sent to the guy she was seeing”

Welcome to Kiss and Tell, a series about the steamy, surprising and frequently absurd world of Toronto dating. Send your most memorable stories from the pursuit of love and lust in the city to submissions@torontolife.com.

—As told to Juliann Garisto

One night, I was at the Horseshoe Tavern trying to hook up with this guy who played in a Kingston rock band. I’d seen the band before, and honestly, they were aggressively mediocre, but all the members were super attractive. The drummer had sexy arms, the bassist looked like a young Iggy Pop and the guitarist was tall with an expertly groomed beard. Then there was Max, the lead singer, who I was there to see. He had that ineffable frontman charm and looked like a mix between Jim Morrison and Jack Black.

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According to hearsay, Max’s dad was part of his own rock band and had some clout in the Canadian music industry. I thought that was cool, and it made me even more inclined to try to get with Max. So I took my best friend Sabrina with me to watch their set. She’s a bit socially awkward but very cute.

When they started playing, we pushed through the crowd to get to the very front. I actually got scratches on my arms from all the girls we shoved out of our way. But I didn’t really notice at the time, probably because I was amped up on alcohol and adrenalin. I then spent the entirety of their set trying to lock eyes with Max. I danced to the upbeat songs and swayed when the rhythm slowed down. Between songs, I would cross my arms tight across my chest to make it pop. Whether it was my energy or my cleavage—or both—Max did end up noticing. He made flirty eyes at me, and I knew I would be able to approach him after the show.

Sure enough, as the band was packing up, Max and I exchanged hellos, and he slipped me a piece of paper with his number on it. When I looked behind me to check on Sabrina, I was astonished to see that she was talking to Simon, the lanky guitarist. As it turned out, they also exchanged numbers. The fact that my best friend and I had simultaneously scored digits from hot musicians made me deliriously happy.

They were headed straight back to Kingston but told us they would be returning to Toronto the next week for an extended stay. They had applied to some residency program in the city and, despite their mediocrity, had actually gotten it. Sabrina and I were stoked about these new connections, but neither of us was looking for anything serious—especially considering that these were musicians.

There was just one problem: Sabrina was struggling to text Simon. She complained that she didn’t know how to talk to him. “He’s just so beautiful,” she’d say. “What if I say something dumb?” She’s a lot shyer than I am and less inclined to flirt, so I really needed to pump her up. The stakes for texting were high—we didn’t want them to forget about us before they got back into town.

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Sabrina asked me how Max and I were texting, so I let her scroll through our history and see for herself. For example, she read aloud a text where I’d written, I just ordered a new set of lingerie from La Senza ;). “There’s no way I can get away with saying that,” she said. It didn’t seem like my examples helped her much.

Admittedly, I’m pretty forward in my romantic interactions, but I still thought she was being silly. After I’d done everything I could to encourage her, I finally told her to hand me her phone. I opened her text conversation with Simon and just wrote, Hey, how’s it going? He responded immediately, which made Sabrina panic. I ended up texting him for the rest of the night, with Sabrina gazing over my shoulder. It was an innocent conversation about what we’d each done that day, and then Simon sent some song recommendations. I told Sabrina to listen to the songs in case they ended up meeting in person and he asked about them.

Soon enough, Max and Simon were back in Toronto. Max and I started seeing each other regularly, and so did Simon and Sabrina. Sometimes all four of us would hang out. But Sabrina was still in a constant state of fear over how to text him. So I continued writing every single message she sent him. She’d hand me her phone whenever he reached out. If we weren’t physically together, she’d send me screenshots of his messages.

I enjoyed crafting messages to Simon—it made me feel like I was living a double life. I liked the idea of the four of us as this pair of power couples. More than anything, though, I liked double-dating with my bestie. I guess I could have encouraged her to take over eventually, but it was easier and more fun to message on her behalf. It never felt weird, even when the messages got flirty.

About two months into all this, I ended up moving in with Sabrina. A few weeks later, I was in my room when Sabrina texted me the siren emoji—a signal that she needed my help. I joined her in the living room, where she and her phone were on opposite ends of the couch. I knew her passcode, so I opened the text convo with Simon and sent him a joke. It was nothing special, so much so that I don’t even remember it. What I didn’t realize was that I’d already made the exact same joke to Max.

Related: “My Hinge date started ignoring me. It turned out he was buying concert tickets”

A couple of days later, I got a text from Simon asking why Sabrina was stealing my jokes. It became evident that Simon had shared the joke with Max and that Max, having already heard the joke, had realized that something was up. I tried to cover my tracks by saying that Sabrina was just a joke stealer, but the boys were on to us. Simon told me that he and Max had been comparing text messages and noticing other similarities. Shit, I thought, the jig is up.

I called Simon while Sabrina was sitting next to me on the couch. I told him everything. Then he asked if Sabrina and I were free to meet him and Max at a bar. We went, and Simon got me to repeat everything I’d said to him, but this time in front of Max. They were surprised, and they had a lot of questions. We gave them honest answers, even though it was uncomfortable. Had it ever been Sabrina texting Simon? No. Why hadn’t Sabrina just told Simon that she didn’t like texting? Because she wanted him to like her. I’d lied to them for months—didn’t I have a conscience? Maybe not. After a couple of drinks, we tentatively made a few jokes about it to lighten the mood. The boys were grinning, and it seemed like maybe it wasn’t such a big deal.

But then, in the days after that, there was total radio silence from Simon and Max. I started to wonder if we’d actually hurt their feelings. On the third day, I texted Max to ask if things were okay and if he wanted to come over later. His reply: Hold on—let me get Simon to reply for me. Ouch, but fair. I guess they were a bit upset after all.

Both relationships had basically ended at that point. We did manage to all have one last hang as their residency was wrapping up, but it was strictly platonic. Since then, I’m happy to say that I’ve had better things to do than handle my friend’s text correspondence. As for Sabrina, she’s learning to embrace being awkward instead of running from it.