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My Dating Dilemma as a Girl in Her Late 20’s

My Dating Dilemma as a Girl in Her Late 20’s

When I was 21, I was pretty sure I was going to be engaged and married to the love of my life at 25. Then, when that relationship didn’t work out, I thought I was going to marry the next love of my life at 27.

Well, I just turned 27 and I’ve been single for 6 months and counting. 

I couldn’t help but think that this is such an interesting time of my life. I’ve been in some form of romantic relationship since I turned 15 and there were never big gaps in between each relationship. In the last couple of years, however, things started to take a different turn. Before my last relationship, I’ve been single for 8 months. Then this time, who knows…

The shift however, is apparent to me though. And it’s not until I take a look at the gradual shift in my relationship history did I realize why this is so.


My first relationship is with Ted. We dated for a year and a half, and he was my first boyfriend. He set the standard for the next guy who came into my life whose name also started with a T. This Mr. T and I dated for almost 6 years, with major on and off periods. He was the kind of boyfriend who fits the bill at that time. He brought me lunch, was tall and cute, and made me laugh, but what I didn’t understand is what it meant to love someone when I was with him.

I didn’t understand what it truly means to love someone, so completely, that your whole life gets sucked into the relationship and into making it work. I didn’t understand what passion is until I met Mr. A.

Mr. A. was an interesting guy who had a lot of things that I wanted. He made me laugh, he was sweet and romantic, ambitious and kind. He was athletic and made it obvious that he cared about me. There were moments when we would lie in bed and just talk about whatever the heck we wanted and it would be fun. He taught me what it means to feel alive in a relationship, until it didn’t.

I loved Mr. A. with all of my heart as the young 23 year old who was willing to follow him to the ends of the earth, but something didn’t feel quite right. He didn’t want to do the same and there were all sorts of obstacles in the way that broke my spirit. So, things came to an end with Mr. A and it hurt so much that I was thrown into long 8 months of self-reflection, growth, and learning to forgive him and myself.

The thing is, Mr. A. had all the makings of the guy I would love to share my life with, but he wasn’t there yet in many ways like maturity and stage in life whereas I was a bit ahead, but I am confident that one day he will be. I have no doubt, that whoever Mr. A ends up with will be a very lucky gal.

Though the timing wasn’t quite right, he set the standard for the next man to come… and I realized, with each relationship, it became harder and harder to find the next Mister in my life.

Then of course, I met Mr. E. A.k.a. Moose. Meeting him, was unexpected after an 8 month gap of Single Lesley. And oh boy, did this relationship change my perspective. The thing is, the gap of non-dating made me stronger, more capable of knowing what I want. I didn’t fall into relationships anymore because I didn’t need to. I was on my way of being comfortable with myself.

And it was true because when I met Moose, I recognized in my gut that he would be worth being ‘in a relationship’ for because being in a relationship was no longer about having fun and having a companion to eat lunch with. It had trade offs.

Being in a relationship meant sacrificing my needs and wants sometimes, and putting my emotions and heart on the line. It meant trying to fit another person’s goals and dreams into your life. It meant I was willing to risk getting hurt again and being considerate of the other person in all your life decisions. It meant, giving up time to chase after my hobbies and working towards my dreams for dates and phone calls.

But he was worth it at that time, and I knew. So trust me on this, you will know when someone is worth it. You see, after dating all those other Misters, I took away nuggets of information subconsciously. I knew what I liked, what I didn’t. I learned how to communicate and how I reacted to my gut instincts. He showed me how I should be treated in an adult relationship and he made me understand what it means to be valued.

To this day, I still ponder about how and why it ended. Perhaps it is timing or we weren’t quite right for each other? But that feeling of coming so close, to falling in this mature yet fairytale like kind of love, still lingers. But it definitely makes it harder for me to date the next man.

So, why did I just summarize my entire relationship history?

Because here’s what I noticed:

  1. My relationships have gotten progressively better and so have my partners
  2. Alone time has allowed me to find partners who are better for me in the long run
  3. Timing is key to successful relationships, sometimes relationships end because of lack of maturity or it started in the wrong place and time
  4. The key to a successful relationship could be finding someone who is the end result of all the things you’ve learned from your previous relationships and then a mix of good timing and a huge dose of commitment
  5. Trust yourself more, because subconsciously, you know what’s best for you and the kind of love you are looking for (You don’t have to convince yourself to like someone, and you shouldn’t date someone because you feel guilty or feel like you owe them)
  6. Life takes unexpected turns, so don’t set expectations for when you’re going to achieve things as important as who you’re going to spend the rest of your life with

Here’s the dilemma:

Society deems that we should date and be partnered up, and perhaps, married before you’re 30.

Then you get lonely. 

The thought of dating crosses my mind often and I’ve been on dates here and there. But, it’s kind of funny, I don’t fall as easily anymore and I am even closer to knowing exactly what I want.

I know it’s silly of me, but because I know that feeling of love that I had experienced in those certain fleeting moments, I don’t settle for less than that, or try to change my expectations to fit those of the other person (e.g. If the other person wants something casual and I want something more serious, I walk away).

I much rather, do my own thing, follow my own dreams, chase after what makes my heart beats, than go on more dates with people who I don’t feel connected to. Sometimes, I catch myself trying to reason myself into giving more chances to men who just don’t feel quite right to me.

Maybe, that’s just the symptom of being a hopeless romantic.

Because there’s one thing that I can’t seem to unlearn. It’s believing in a magical, passionate kind of love. It’s giving all of my heart to one person who I know I can trust to spend the rest of my life with. It’s believing that all of this searching will come to fruition one day.

So yes, I am single by choice… and it’s been 6 months and counting.

As a girl in her late 20’s, I’ve learned that it is easier to say no to people who don’t make sense to you because you’re worth so much more.

Despite what society says, age and all, I still believe in that saying… while I’m off chasing my dreams, I’ll meet the love of my life. When we meet, there will be fireworks and my heart will feel like it’s home.

Call me crazy, but I will not settle for anything less. 

Until then, I have the strength to walk alone.

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