Dating can be a bitch for a hundred reasons, but it’s perhaps at its bitchiest when your emotions get involved before you’re ready. As much as I try to let logic and reason rule in the early stages, it’s not always easy, especially when you meet someone you feel an immediate connection with. This was the case with Trent.

Trent found me online and sent me a message, and though he lived several states away, I replied because it was obvious we had things in common. Plus he was hot. And tall. And adorable. So this was a no-brainer. Trent and I struck up an email conversation, which turned to texts, which turned to phone calls, and soon we were communicating daily.

The next obvious step: Meet in person.

Since he lived a ways from me, this wasn’t going to be as easy as, “Let’s grab a glass of wine on Friday night.” But soon enough, he booked a trip to California and we began making plans. A little background on Trent: He was a widower. At 49. He had lost his wife (whom I could tell he deeply loved) four years ago in a car accident, and though he’d dated since, he had never moved on to another relationship. Did this make me nervous? Of course. Whether or not he was ready to do so remained to be seen–but given all we had in common and the connection we felt through our long-distance interaction, I was hopeful.

One of the things I’ve realized at this stage of life is that, while opposites may attract, they don’t always last. That’s why I’m interested in men who are more similar to me than they are different. Trent liked what I liked, we shared similar passions, and I could talk to him on the phone for five hours but barely feel like an hour had passed. All good signs that we might be able to connect in person.

So Trent and I didn’t start with a “date,” per se–we started with a vacation. He traveled to California for a week, and I took time off to be his hostess and tour guide. After our first evening together, sipping wine, sampling cheeses and talking for several hours at my place (with a few kisses thrown in the mix), I was pretty sure I’d want my role in his life to morph into something more, but it was early . . . and I was trying to be patient. So I concentrated on simply having fun with him.

The next day, we walked along beautiful cliffs with amazing views of the Pacific in Santa Cruz. Relaxed at a wine bar on the water underneath a full moon. Toured San Francisco the day after that. And then traveled to Sonoma for a weekend of wine tasting. Through it all, I was smitten. Trent was kind, humble, affectionate, charming and I loved how he looked at me. You know what I’m talking about–that look a man gives you that says, “You’re amazing and I’m crazy about you” without a word. And I’m pretty sure I was looking at him the same way. There was no mistaking our chemistry, and butterflies were flapping all over the place. I knew, early on, that this man could capture my heart.

The problem was, it didn’t take long to discover that his was already captured. Still. By his late wife.

We had chemistry, yes. Physical attraction, no doubt. There was a connection, absolutely. But his heart–well, that was a whole different story. By about the third day, I could tell that Trent was still madly in love with his deceased wife (whom he still called “my wife”), and many of our conversations would eventually lead back to something about Amy and how much he loved her and what an amazing woman she was and even how hot their sex life was (I shut that conversation down quickly–I didn’t need to hear details).

If he complimented me on something, it was usually followed up with something like, “that’s how Amy was,” or “Amy would do the same thing.”

Our day in San Francisco was like a trip down memory lane for him about the last time he’d been in the city. With his wife. In 2009. A year before her death.

And our wine tasting tour in Sonoma? Well, let’s just say I immediately felt like a third wheel when, at our first winery, Trent showed me the chain he was wearing around his neck containing Amy’s ashes. This was a “tribute tour” to her, he told me. And I guess I was just along for the ride?

Good thing I’d spent $200 on a driver for us that day–I wouldn’t have wanted either of us to worry about drinking and driving as we were toasting to this woman whom I would clearly never live up to.

When I dropped Trent off at the airport the following Tuesday morning, I knew I’d never see him again. Even though we had plans to meet in Chicago for New Year’s Eve in three weeks, I knew it wouldn’t happen. I was ready to explore a relationship with him. I was tired of dating men with no connection, fending off unwanted advances, clearing unsolicited dick pics off my phone and kissing frogs with no prince in sight. Trent was different, and I didn’t want to let go of that.

But he wasn’t ready. I think he wanted to be. But the truth is, he wasn’t. He emailed me the day after he got home to tell me that my having to “analyze” everything and the “emotional roller coaster” from the weekend made him pull away and place me squarely in the friend zone.

I guess that’s what I get for asking questions like, “Are you really ready to move on?” and “Do you believe that you can have another great love in your life?” Maybe it was too early for that? Maybe I should have let all the talk about Amy continue and just shrug it off and chalk it up to normal widower conversation. Maybe I should have been okay with the possibility of being second best in his life.

But here’s the deal: I am ready for a great love. And whoever I share my heart with will never be second best . . . he will take the top spot. Call me greedy, but I need to know that it will be the same for him.

Someday Trent will be ready to move on, and the woman who’s there when he is, well . . . she will be a lucky gal. He’s a great catch.

But so am I. And someday there will be a kind, humble, affectionate, charming and emotionally available man who gets that. Cheers to meeting that prince.

-Sienna