Why Do I Stay In Fun Relationships That Are On The Fast Track to Nowhere?

Sometimes I watch myself date from above, like a god, OK let’s be real, more like a friend in a healthy relationship, looking down from an airplane, and I think “What are you doing?” I float there, knowing full well that every word coming out of a guy’s mouth is BS, and every frustration I’m feeling is totally valid, and yet, I let it happen. I let myself continue to enter into what I know is the wrong thing. I’m not talking about a gut wrenching, heartbreaking saga, I usually have enough control to stop myself before I get there, but I do like to get my toes wet, dip my feet in a little too deep into the world of dating with fire. The kinds of dates that are fun, but lead nowhere. They’re exciting enough to keep me engaged, but dysfunctional enough to keep me distant. And yet, I never come out unscathed.

I’m a rational thinker. Sure, I can be impulsive, but I tend to look at things discerningly. I trust sparingly, and yet, I trick myself easily.

Recently I dated a guy who frustrated me to no end. He showed up late. He pushed off dates. He missed phone calls, and then he’d follow up the next day with the most casual “what’s good?” as if nothing was wrong. He was fun, he was smart, he made me laugh and he confided in me. And yet, he couldn’t set a plan until the day of, and he’d cancel on me for work with few apologies. I told him I wanted to date, he told me he wanted something more chill. 

And yet, every so often, my phone would buzz, and his name would pop up, and I couldn’t help but indulge in his banter.


Well why not,I would tell myself. You know he’s not going to give you anything serious, and you have nothing else going on right now. What’s one more flirty text, if I know I’m in control? If I’m wholly aware of all of the consequences, I can’t get hurt, right?

I admire anyone who is self aware. I think it’s the best way you can be. And so I tell myself that’s what I’m being. Except, is it possible to be self aware of your self awareness, so much so that it undoes the whole thing? That you become so entangled in yourself that you’ve managed to convince yourself you know best, but really you know absolutely nothing?

I spent years taking my dating life too seriously. Date for marriage. That’s the slogan of my community. And after years of sitting through stiff dinners and awkward drinks, I’ve finally reached a point where I’m starting to just have fun with it. Which I think on so many levels is amazing. It’s leading me to people and experiences I never would have met or had. I’ve downloaded apps and gone to parties I never would’ve gone to when I first graduated college. I’ve dated guys younger than my youngest brother, said yes to dates with men with non traditional jobs, tried new drinks and new foods, explored different neighborhoods, learned about new industries and different ways to relate to god and religion, found new music I liked, and bands I hate, and honestly, I’ve become much more secure in who I am, and all because I was ready to finally have fun and take dating and myself a little less seriously. And that’s what I’m doing. Having fun. All the while knowing that the little voice in the back of my head, the one that’s watching from above, will every so often chime in and say “what are you doing?” And it’s good to know I can still check myself. But is it enough if I don’t always listen?

They say hindsight is 20/20. Well, the truth is, sometimes living through something is just as crystal clear, and yet for some reason, sometimes you just don’t want to see. I’d rather put down my shades and go just a bit longer. Because, sure relationships are hard, but dating, is really damn hard, even when it’s fun. And being able to look from afar and separate yourself, well sometimes even the most educated, self aware of us all, need a little time to get there.



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