Confessions of a Dating Disaster

Author: Mary Grace Donaldson, The Dating Game

Millennials, I’m about to let you all in on a little secret. While I don’t necessarily hope that you can relate, I’m willing to bet that some of you can.

I’m a dating disaster.

While I’ve been able to open up about some of my past experiences and personality quirks, it’s easier for me to write than speak sometimes and as a result, I’m pretty closed off. While I’m talkative with “adultier adults,” and with people I know very well, I also get nervous when meeting people.

Which makes dating… well, difficult.

I’ve been through a litany of disaster dates and situations — from the time that I completely embarrassed myself on a blind date, to the time I thought I was on a date but it was not a date… from unrequited love to “friends with benefits” to two failed profiles on dating sites while I was in college to making a dramatic exit from the fast-food restaurant where my college “boyfriend” (who may or may not have actually been my boyfriend) worked. And while it takes a lot for me to admit this, it gets frustrating.

Yes, I laugh about it. Yes, they all make for great stories that I tell with such dramatic flair when given the right audience that you’d think I’m performing stand-up comedy. Yes, I fully believe that there’s nothing wrong with being single… though I can list lectures 1-54 from my best friend on the subject of how I push people away and how happy he’d be should I manage to find a mate to the point that I think he’d wave pom-poms in my face. And what do I do? I stand there rolling my eyes.


But if we take all of the funny window trimmings away, sometimes, it’s a drag being a dating disaster, who either pushes away any potential mate who may get too close or who makes up scenarios in her head that will never ever happen… with the wrong person. My philosophy that it’s better to be upfront about feelings than to beat around the bush probably doesn’t score me any points in the wrong situation either — and my declarations of “I like you” or even worse, “I love you,” that went unrequited have not helped.

And you can’t help but wonder: is it me? Is there something wrong with me?

Millennials, I’m here to tell you that it’s normal to have that feeling. Your stupid, crazy and even hurtful experiences can truly shape your outlook to the point at which you can’t help but wonder if you’re the only common denominator in these situations. And I’m also here to tell you that such thoughts have not disappeared from my mind even as I write this.

But it’s also important to remember a few things when you have those thoughts.

Dating is different for us than it was for our parents. Not necessarily bad, but different. And it’s okay if you long for a dating world that you’ve never had — I know that I do. But it’s not you. It’s not even the other person you’re currently seeing or those you’ve dated in the past. It’s the dating world in which we live.

But, don’t give up, fellow dating disasters — that is, of course, if this is something you want. If it’s not, that’s more than okay. But if it is, don’t ever stop being who you are. Remember: there’s someone out there for everyone.

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