One Night with Becky: Chapter 7

I stopped checking the dating apps. I just couldn’t handle the disappointment anymore. Every swipe, every face… it was like I thought I would swipe and see Becky along with ’New Match!’, but it never happened, because it was an impossible fantasy. So I left those damned apps alone.

At first, it was just a day. Then two. Then a week passed, and I realized I hadn’t opened Tinder, hadn’t swiped, hadn’t stared at filtered photos wondering if maybe this one would be different. Maybe I had just… given up. Maybe the idea of having nothing was better than the idea of settling for something that didn’t make me exciting. At least this way I didn’t have the guilt of giving some innocent person the wrong idea.

I stopped going out too. No bars. No cafes with the hope of bumping into some cutie. No more late-night scrolling through escort sites, hoping to find some physical Becky match that could satisfy me temporarily.

I just… stopped…

And for a while, it was disorienting. The world seemed grey and lifeless, and I wondered at times what the point of it all was. 

I spent a lot of time alone. Not in some depressing, pathetic kind of way where I was in some concrete room with no windows, with the lights turned off. 

Just… quiet. 

Me and my apartment. My couch. Old books and movies I hadn’t touched in years. A drawing hobby that I never fully realized. Some free weights I bought a year earlier thinking I would start to get in shape.

I even started walking in the evenings—not expecting to meet anyone, but just to keep myself active. I started really enjoying being out when the sun was setting. I started to enjoy stopping in at the library and swapping out books. 

My life had become… still, but in a calming sort of way. Maybe it was a bit sad at first, but soon, I started to appreciate the peace and quiet. 

And it was in that stillness that I started to see things more clearly.

I started to think more about the Becky situation—not so much about Becky, but about all of the feelings that came during and after that date. I started to try to unravel what had happened inside of me.

Every time I’d thought I was chasing love, I was really just chasing distraction. From what, I wasn’t even sure. From Becky, maybe. 

But it went deeper than her. 

I’d been chasing something long before she entered the picture. Some hole inside me that I didn’t want to sit with long enough to identify.

Becky had just lit it up.

And every girl since had been another attempt to cover it.

I thought if I found someone else like her—someone beautiful, charismatic, and valuable—I would be satisfied. I knew that thousands of other guys wanted that date that I won, and I guess that made her seem like she was so valuable—something that I needed to have, like a dog guarding a bone. And then, during that date, Becky made me feel like I mattered, like I was just as valuable to her as she was to me. It was fake, of course, but the feeling was there. 

What I’d really wanted was validation. Proof that I mattered. That I was desirable. That I could still be wanted by someone special.

The problem was, none of those women ever had a fair shot at being anything but a stand-in. I didn’t want them. I wanted a second chance at that first high. A rerun of a story that was never even real to begin with.

That was the part that stung the most.

Because Becky had never promised me anything. I was the one who wrote the fairy tale. I’d created that fantasy, and then I’d blamed her when she didn’t act accordingly.

And I realized something else too…

I’d been treating these trans women like some secret door to a deeper love story. Like they were some key to the mystery that had been plaguing me my whole life—or maybe like some shortcut to the love that I wanted, because I felt it for a moment with Becky. I’d never stopped to consider what it was like for them—to be seen that way. To be held up to impossible expectations. To be constantly compared to something that never really existed. 

I felt ashamed. Not for trying, but for why I was trying. It wasn’t love I’d been after. It was some sort of escape.

I had to sit with that… for days… weeks… months…

Slowly, the ache softened. Something deep inside of me was telling me to stop looking for love, that I just wasn’t ready for that yet.

So I stopped.

I let the quiet stay. I let go of the idea that the next person would fix me and my problems. 

*

It started with a message.

Not from a dating app. Not a push notification or some algorithmically generated “perfect match.” Just a simple text message from a name that I didn’t expect to see pop up.

“Hey. Just wanted to say hi. Hope you're doing okay.” It was from Jenna.

I stared at it, surprised to see that name. I felt a weird stumbling in my chest. My date with Jenna had been a bit awkward. Not terrible… but awkward. And the way we left off just felt… unresolved. I thought that she hated me for having sex with her and then not reaching out again. I assumed that she had just assumed I used her for sex, but it was way more complicated than that—too complicated to try and explain to her, so I did the cowardly thing and just moved on as if the date never happened. Now, she was reaching out, maybe looking for answers. 

After a moment, I replied.

“Hey! Thanks for checking in. I’m… yeah. I’ve been better. You?”

She answered quickly. “I’ve been okay. Started a painting class. I’m terrible, but it’s fun.”

I smiled, picturing her saying that—half-serious, half-shy, probably tucking a loose strand of hair behind her ear. I have to admit that Jenna was cute in her own way. Sure, she had some more masculine features, but she was still early in her transition. 

We messaged for a while. The conversation came surprisingly easy. She didn’t seem to have any resentment for my ‘ghosting’ her. There was no pressure. I didn’t feel like I needed to pretend to be something else to impress her. I even ended up apologizing for not reaching out. “I was going through some stuff and I just didn’t want to pull you into that,” I told her. 

“It’s okay. I was… going through my own things.” 

Eventually, I sent one more message. “You know… I’ve been thinking about that night we hung out. I know it didn’t go so great. But I actually liked talking to you.”

A long pause.

Then: “Yeah. I’ve thought about it too. It was a bit clunky for sure. But it really wasn’t the worst date that I’ve ever been on.”

I hesitated. Then typed:

“Would you want to grab a coffee sometime? No pressure,” I said.

I watched the screen as the typing dots came and went.

Then finally: “Yeah. Let’s do that.”

We met at a quiet, slightly run-down coffee shop that looked like it hadn’t been updated since the early 2000s. Vinyl booths, faded posters of coffee beans on the walls, and jazz music that nobody asked for. 

She was already there, sitting by the window with a cappuccino in front of her and a scarf wrapped tight around her shoulders. I hesitated a moment. She looked better. She was a few months deeper into her transition: a few more months of hormonal changes, a few more months practising her makeup, growing out her hair, figuring out her mannerisms and posture. 

“Hey there,” she said as I approached.

“Hey,” I said, sliding into the seat across from her.

She smiled softly, but her hands stayed curled around her mug.

“You look good,” I said.

“So do you,” said Jenna. “Less… frazzled.” She giggled. That giggle sounded a bit more feminine too. Her voice wasn’t perfect. A step in the feminine direction from last time for sure, but still not perfect. Though it didn’t really matter. 

I laughed. “Yeah. I’ve been trying to slow down a bit. Deleting things… I’d like to think that I’m less frazzled.” 

She raised an eyebrow. “Deleting things?”

“Dating apps,” I said. “All of them.” I felt my cheeks redden. 

Jenna tilted her head. “Even Tinder?”

“Oh, of course. Even Tinder.”

“Wow.” 

She seemed less shy. Maybe it was my own energy. When we first met, I was so tense, so high-strung, and that probably made me hard to talk to. Now, I was more relaxed—and she seemed to have settled more into her identity. 

I smiled. “I’ve been… kind of re-evaluating a lot of my life, I guess you could say.”

Jenna nodded and looked down at her drink. “I get it. I’ve been doing some of that myself.”

It was silent for a moment, but it didn’t feel awkward—not like before. This was a mutual silence. Just quiet. Gentle. Comfortable. I looked at her, seeing her in a different light than before. Her little flaws that seemed so inexcusable before seemed curiously endearing now. I felt guilty for having ever thought they were flaws at all. I suppose they were never flaws—they were just the qualities that made her different from Becky. Hell… now, they were highlights—a nice reminder that she wasn’t Becky. 

“So how’s the painting going?” I asked.

“Oh, terrible,” said Jenna, laughing. “I glued a canvas to the floor by accident last week. Not even kidding. I had this idea to create more texture by mixing glue into the paint… Well, not so much my idea as something I saw on TikTok… But anyway, I did it with the canvas on the floor so that the glue-paint wouldn’t drip down… Long story short, there’s art on my floor now, and it’s there for good.” 

“Installation art,” I said, grinning. “Bold move. It will increase the property value.”

“Hopefully my landlord agrees.” She giggled again. I was really starting to like that giggle. 

We talked about nothing and everything. About music. About what we were reading. About movies we’d seen and movies we hadn’t seen yet. 

“I don’t really know what I’m looking for right now,” I said eventually, unprompted. It just felt like something I needed to say: an honesty that I needed to be upfront with. I didn’t want her thinking that I was there with expectations or assumptions. 

I was just there for… fun. I was still sitting there because I was enjoying our time together, and that didn’t have to mean that this needed to ‘go’ anywhere. 

Jenna looked at me carefully. “Me neither. But I wouldn’t mind figuring it out… someday… with the right person.” 

I nodded.

“Yeah,” I said. “Me too.”

And for the first time in a long time, it didn’t feel like I was chasing anything. In fact, it wasn’t until much later that night that I even thought about Becky, and it was just for a quick moment when I logged onto my computer and saw one of Becky’s websites in the ‘frequently visited’ tab. I decided then to clear my browsing history, and after that, I never did see anything from Becky again. Maybe I thought about her a couple of times here and there for brief moments. It’s not like I was able to erase those memories completely from my brain. Those memories were there and always would be there. 

But after meeting up with Jenna, I did manage to erase something from those memories: that feeling of attachment that used to come whenever I thought about Becky. Now, the only emotion that sparked up when I thought about Becky was embarrassment—not from having hooked up with her, but from being so wildly obsessed with finding her qualities in other people. 

A few nights later (after a couple more meetups), I ended up at Jenna’s place to watch a movie, and when the movie ended, I got a chance for a redo. We kissed. We undressed. We explored each other tenderly. I sucked her and she sucked me. This time, I was only thinking about her. This time, I was able to appreciate what she had to offer as her own unique person. Jenna wasn’t some expert porn-star. She didn’t have some fourteen-inch monster-cock. She was just herself. She was who she was—and that was enough. 

THE END