I've been single for close to a decade and I have a lot of stories that go, I could have done this, or I should have done that. As I notched a year into my 30s, I vowed that I would take more risks when it comes to pursuing women. I no longer wanted to wonder about what ifs in life.

It was then that I met Gwen at an office gathering. We've been working at the same company for two years and have a lot of common friends, yet our paths never crossed until that night. I have to admit, I immediately had a crush on her. We briefly spoke, but nothing really came out of it.

It would take another four months and another office party for Gwen and I to really talk. I realized then that I really liked her. Since we have a lot of common friends, I slowly eased myself into her inner circle. We also had long conversations over Facebook and exchanged text messages.

One night after work, I finally had the guts to ask Gwen out. She immediately clarified if I meant on a date. When I concurred, she was honest, saying, that though she was dating, she wasn't really looking. She recently came out of a long-term relationship and was just looking to enjoy life and concentrate on her career.

I understood this but I also knew I didn't want to add another what if story to the long list I had. I told her that I wanted to pursue her. That I wasn't in a rush, and that I'd like the chance to get to know her. We could take it slow. I convinced her enough to say yes, or maybe because it was already late at night.

During our first date, I was rather nervous, wanting to impress. Gwen was calm, she asked a lot of honest questions as did I. I've never been on a date where you simply can just talk and we laughed a lot—even about how awkward we both are.

That night was followed by a number of dates and hangouts. The conversation just flowed. We started opening up about our families, dreams, and stories from our past. When I asked, she even talked about the other guys she was seeing. We were so honest to the point that it scared me a bit. But it was refreshing. Gwen was smart, and I felt we connected intellectually—something I've never experienced before.

Things seemed to be progressing, but I knew how to temper my expectations. Every time we're on a date, Gwen would often tell me to date other people like she was. By choice, I didn't. I wanted to show her that I'm serious about her, and that I meant it when I said I wanted to pursue her.

I didn't tell her this, but the moment she said yes to our first date, I made a decision to wait. Yes, she wasn't ready, but isn't the goal of dating to eventually lead to something? I've never done this in the past and I felt that our connection was growing. This was a conscious choice.

As the months went by, friends wondered how we were. While most of them were happy for us, some also questioned the uncertainties. One of them even asked "Why treat someone like a priority when you're only just an option?" Deep down, I knew what I was getting myself into; I knew there was a chance that it wouldn't work out.

And indeed, it didn't. Around the four-month mark, Gwen decided that it wasn't working and that it wasn't a good idea for us to keep dating. This caught me off-guard. I really felt that we were progressing. Where did I go wrong? Much as I wanted answers, I chose to distance myself from her which was hard considering we have so many common friends and worked in the same office.

There were chances for me to ask her the many questions I had, but in her words, we were, after all "just dating." It's not as if we were in a relationship. I tried to manage my expectations from the start, but like any one who dates, I became hopeful and fell deeper than I expected. Gwen simply didn't feel the same. 

Do I regret my decision to wait for a lady who wasn't ready? Not one bit. I made a conscious choice to pursue Gwen. I followed my instincts and did the best I could to show her how much I cared. Perhaps, I became too available, in the eyes of some, but I also just don't spend time and pour my efforts on just any woman either.

There are still nights when I think of the shoulda, woulda, couldas. But if things are truly meant to be, everything will just fall into place. Complications will easily figure themselves out, too. I had the chance to try and win Gwen's affection and I didn't. That's just how stories end, sometimes. 

SCREENCAP: How I Met Your Mother/CBS

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