Imagine this: I’ve been on so many dates that my friends started calling me "The Serial Dater." I've seen it all—dinners, coffees, awkward silences, and too many men with the personality of a plank of wood.
Finally, just when I thought I had met "The One," and the romantic comedy of my life was about to hit its happily-ever-after, the plot twisted harder than a kid going down a helter-skelter. Turns out, "The One" was just another Mr. Wrong, leaving me with nothing but another story and a new resolve.
Three years ago, I found myself in a peculiar romantic limbo. After dating someone for ten months—yes, I hear you gasping, "Ten months?"—we never quite got around to the official "boyfriend-girlfriend" labels. It was one of those situations where we got along so well platonically that we convinced ourselves we could make it work romantically. Spoiler alert: we couldn't. Cue the inevitable breakup and my subsequent dive into the unpredictable world of dating.
Since then, I've been on more dates than I care to count and the staffroom has become my personal therapy lounge. "You're so picky," "What's wrong with them this time?" are just a few of the remarks I get from my colleagues when I tell them the 125th story of how I've got the ick. If there were an Olympic sport for catching red flags, I'd be a gold medallist by now.
Although in the last three years I have a couple of almost-romances. The first was two years ago with a guy I went on four amazing dates with. Just as I started to think he might be "the one," he rekindled things with his ex. Can't compete with an ex, right? Especially when the "what if" scenarios start messing with their heads. Well, it worked out great for him—they're now engaged. Everything happens for a reason, or so they say.
And the second guy? Rewind four months, and I'm juggling conversations with two guys—let's call them Jake and Tom. Tom and I hit it off right away. Our conversations flowed effortlessly, and when we finally met up, there was an instant spark. It felt incredible to experience that kind of connection again after two years. At the end of our first date, he messaged me saying he couldn't wait to see me again. Cue a two-week wait. In the grand scheme of life, two weeks is nothing, but in the dating world, it's an eternity!
We finally met up again, had another fantastic date, and he told me once more that he couldn't wait to see me. And then... another two-week intermission. It was like dating in slow motion, with more pauses than a poorly buffered YouTube video. Back to the drawing board. Jake pops back up and invites me for a drink. I don't know whether to go; he was nice, but his messages were a little flat. What harm is there in going? I accept but don’t expect him to blow me away. How wrong I was. He was interesting, funny, charming, good-looking, sweet, courteous—just lovely. We have an incredible date, the kind where you just don't want it to end. He messages me asking when he can see me again. We set a date for two days' time, and he’ll make the plans. Jackpot! This is what I need—someone who knows what they want and takes control. Exactly what I found Tom was lacking.
Over the next month, we meet up regularly. I feel like a 16-year-old again—completely giddy and constantly thinking about him. I’m like a Cheshire cat (VOM), and everyone is shocked at how much I like this guy. I like the way I am around him. He makes me better. Then he goes on holiday for ten days, which means I don't see him for two weeks. I miss him. What has happened to me? He tells me he feels the same and can't wait to see me when he gets back.
Everything is great when Jake gets home, and then it all starts to change. I can't pinpoint where it went wrong; I just had a gut feeling that something wasn't right. Things at work had gone south for him, and he seemed down. He stopped messaging me as much, didn’t do the little things every day that made me smile. One day, while I’m at work, Jake messages me telling me he’s struggling emotionally at the moment. He says he’s sorry for being awful but that he wants to keep seeing me.
Therefore, I persevere because it's rare I find someone I can actually see myself with, but I end up feeling like a nuisance. I continue to ask him to meet up, which we do, and we have a great time. But in the interim, the messages are flat and become less frequent. Our meet-ups are staggered, and I begin to feel unappreciated and unwanted. This goes on for a few weeks. Fast forward to last week, I tell him how I feel and that I don't think it is going to work. No reply. Silence says it all... he’s just not that into you, Jen!
To say I'm a little gutted is an understatement, but hey ho, life goes on. Plenty more fish in the sea, as they say (I can only hope). After all, who doesn't love a good fishing metaphor when you're swimming in the shallow end of the dating pool?
Cue endless venting sessions with the girls—seriously, where would I be without them? They patiently listened to my constant drone of despair, armed with wine and words of wisdom. It's in these moments of shared laughter and commiseration that my dating blog was born. I hope it to be a sanctuary where I can vent, laugh, and share the rollercoaster ride of my love life. Because if you can't find love, at least you can find humour in the search.
So here I am, turning my romantic misadventures into entertainment. If my dating life can bring a smile to someone's face or make someone feel a little less alone in their own quest for love, then all those awkward first dates and almost-romances were worth it. Because, at the end of the day, laughter is the best matchmaker—even if it sometimes sets you up with a punchline instead of a partner.
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