What Dating Is Like When You’ve Been Disappointed A Lot

Many of us are looking for love and hoping that every romantic encounter we have will finally be that happy ending we’ve been waiting for. Obviously, that’s not usually the case, and when you’ve had your heart broken or been let down by guys a lot, dating can be challenging. Here’s what it’s like to be looking for love when you’ve been constantly disappointed in relationships:

Our walls almost make us seem uninterested. It’s almost as if we can’t let your guard down even for a moment in fear that we’ll be bulldozed again like before. With each disappointment we’ve faced, the guards get thicker, stronger, and more impenetrable. We have a hard time building the romantic intimacies we need to feel that lustful beginning because we’ve done it time and time again, only to be let down. We keep our feelings close and protected until we’re sure.

We search for reasons it might not work out. We’re dying to see how this one ends, because endings are all we’ve grown accustomed to. As sad as it might be, that’s our reality, so forgive us if we’re not swooning madly when you’re charming in the beginning. We’ve heard that song before.

We don’t get overly excited anymore. As much as we want to be those women who open up their hearts and go forth confidently in the direction of their hearts desires, we can’t — at least not right away. It takes us real time, which we’re not used to having, to really feel at ease with things. We’re used to a dozen first dates that don’t lead to seconds. We’re used to being ghosted. We’re used to short-lived experiences and we’re used to starting all over again.

We constantly question what’s wrong with us. We look at other couples and think to ourselves, “Why can’t I have that?” or “Why couldn’t I have just found my person earlier and be done with this endless search?” We sit in these thoughts for longer than we’d like to, but we seriously just can’t help it. It’s hard to rebuild your confidence when it’s constantly kicked from under you time after time.

Our friends feel genuine pain for our heartbreaks. Our friends have heard so many unfortunate stories of our relationship demises that they’ve actually felt real grief from watching us go through it so much — especially when we‘re genuinely and purposefully searching for something real, honest and lasting.

In fact, everyone feels sorry for us. Our parents, our bosses, everyone. It’s legit not even funny anymore and sometimes we get so lost in the shame of our constant failures that we wonder if we should even bother participating any further in the madness.

We don’t give our trust freely. They say trust should be given freely until proven otherwise, but when you’ve been disappointed a lot, that’s easier said than done. You’re an ending waiting to happen until you prove to us just how into us and serious about getting to know us you are. I know this sounds insecure and it probably is, but we can’t help it. We’re willfully hopeful, yet diligently petrified.

We try to be positive, but it’s just so hard. We want to believe in happily ever after — that this one be the one we’ve always wanted — but our personal history kills our hopes. We totally know that it would be way easier if we just behaved as if nothing could go wrong, but we know better, so we choose to be practical instead of losing our heads for possibly no reason.

We try anyway. Despite all of the reasons we doubt, fear and question, we pull our act together and try anyway. Sure, it takes us a while to open up, to drop our guards, and to truly feel an element of trust, but when you’ve been disappointed a lot you can’t help but be cautious. We know in the end that when the right person finds us, the process will have been worth it.

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