The First Date Dilemma

Honestly, I had no idea that Preston was into me. He claimed to be straight, and I took him at his word. There was no reason not to. At first, I wasn't even sure if I liked him as a person.

He was distant and always had a sarcastic remark ready. Looking back, I probably should have fallen for him from the start, but then, this would be a very different story.

Our paths crossed at a writing group. Over time, Preston started joining me for dinners or drinks after our meetings. He bonded with my friends by teasing me about my obsession with cottage cheese, even when I wasn’t dieting.

Then, one night, everything shifted.

“Will you walk with me to the train station?” Preston asked. “There’s something I want to tell you.”

“Yeah, of course,” I replied, feeling a bit puzzled.

I didn’t know what was coming, but I’d learned early on that when someone asks to talk, you don’t say no. Maybe he just wanted to vent about writing or ask for advice about a love interest, I thought.

We weren’t exactly close, but it wasn’t unusual for straight guys to seek my help with women. Most of them knew that gay men often have insights into what women want.

As we strolled, Preston was unusually quiet. For someone who wanted to talk, words just weren't coming out. That worried me.

Before I could ask what was wrong, two mutual friends caught up to us, and whatever Preston wanted to say could wait.

Leaving It for Later

That weekend, I went back to Detroit for my sister’s wedding, where I was giving her away. I needed to be there.

At the wedding, I had a few drinks and finally admitted to my cousin that maybe I was attracted to Preston. Still, I believed there was a boundary — I thought he was straight.

“I don’t think he’s straight,” my cousin said.

“He says he’s straight, that’s all there is to it,” I argued.

“Straight guys don’t tell their gay friends they miss them,” she countered.

“He might. Things are different,” I replied.

When I told a friend about it, she quickly agreed that Preston probably had feelings for me. She pointed out how he always found ways to make me laugh and smile, and even touched me lightly now and then.

But I wasn’t convinced. Preston insisted he was straight, and I accepted that — for now. Or so I thought. Later, I learned that he hadn’t outright said he was straight. His exact words were that he’d only been in one relationship, and it was with a woman. However, he never ruled out being with men.

That revelation stunned me.

“Preston, do you have a crush on me?” I texted.

His reply: “I live outside Manhattan and travel twice a week to see you.” Then he asked, “What do you think?”

That moment, I felt like I’d had too much to drink and decided this conversation was better had face-to-face.

The Talk and a First Date

When I returned to Manhattan, I knew it was time to talk. Preston had the same idea — he asked our mutual friends to give us some privacy.

After our writing group session, we headed to a local pizzeria. We both loved cheap pizza and beers, and it seemed like the perfect setting to discuss what was happening between us.

While waiting in line, I noticed Preston kept trying to hold my hand. I offered my hand, and he took it with a smile. It felt natural and right.

“Is this our first date?” Preston asked, cheeks flushing red.

“Do you want it to be?” I responded, cheeks warming too.

“I do,” he admitted.

Before he could lean in for a kiss, we were called to order. The cashier looked between us, then turned his back, handed Preston a box, and took his payment. The pizza was shaped like a heart. Preston claims it was unintentional, but I have my doubts.

“I really like you,” he said as we took our first bites.

“I like you too,” I responded. “But I thought you were straight, and I didn’t want to risk making things awkward.”

“I never said that,” he replied.

That was the first of many debates in our relationship. Preston and I weren’t your typical couple. We thrived on arguing, challenging each other’s points, and pushing for better reasons.

When the time came to part ways, there was no drama. We both recognized that staying together might make one of us unhappy — and that wasn’t what either of us wanted.

In the end, we chose love — not labels or assumptions.

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