I was sitting in temple recently celebrating Rosh Hashanah, the Jewish New Year, when a friendly couple in their 60s struck up a conversation with me about love and relationships. I’m not quite sure how we got on the subject, but I think it had something to do with the fact that if I had my way, I’d stick to dating guys within the same faith. This was an issue because the guy I had been seeing most recently was not Jewish, and I often wondered how things would progress should they get serious down the road. On the other hand, I thought I had found ‘the one’ with my last boyfriend (who was Jewish) and he ended up breaking my heart. As I had to remind my parents over and over again, just because a guy is Jewish by no means indicates that things will work out. It certainly would have made things easier, but what about life is easy? The man then turned to me and said, ‘but at least now your heart is no longer broken from that young man, right?’ In a day that I thought would never come, I proudly looked at him and said, ‘yes.’

It was a comforting feeling to know that the biggest heartbreak of my life hadn’t ruined my ability to find love again, and could even be better than the last time. Still, the pain of my last relationship was always in the back of my mind, aware that you are never fully exempt from it. It’s like jury duty. You get called in, and whether or not you are excused after one day, or one case, you know that a year later, you’re gonna be thrown back into the jury pool. Boy, oh boy, the fun never stops.

Still, I wanted this newfound happiness to last as long as possible. Too many times it seemed like I always got a taste of the main course, but I never got to finish it (or rather, savor it). For once, I wanted to really be happy and not be constantly looking over my shoulder waiting for the other shoe to drop. Any therapist would tell me that anticipating a problem is never a good way to start off something new, but until I learned differently, experience was all I had to go on.

So even though I kept whatever fears and insecurities I had to myself, it came as no shock to me when my new guy admitted that he was harboring quite a big secret (he was going through a divorce which was continuing to be drawn out thanks to a greedy ex-wife) and the stress of that was stopping him from fully committing to me. Bam! Just like that. What he originally explained as just work stress was actually something so much bigger (he never even admitted to being married when we originally talked about past relationships). So, merely two weeks after solemnly celebrating the Jewish New Year, I found myself with another broken heart. As much as I told myself that one day I’ll be whole again, it didn’t take away the pain that was marinating inside me. Frankly, nothing can. It’s that gut-wrenching, sickening feeling in the pit of your stomach pain that churns inside you like the most dangerous of twisters. You can almost feel the stress hormone cortisol throwing a party inside you, and somehow this feeling like you’re gaining weight even when you’re running at 7.0 mph on the treadmill. You try to convince yourself that you’re just thinking negatively, that things are never as bad as they seem, but your gut—and your heart—knows differently.

With my last relationship, I tried endlessly to make things work. But if you’re dealing with a liar and a cheater, no matter how much you try to do the right thing, it’s like trying to teach a politician to remain faithful (well, many of them, anyway). Forget it. They have to want to change, and more importantly, recognize there is a problem worthy of change. With my newest relationship, I was dealing with heartbreak far worse than what I had been through before. He knew he was a work in progress and needed to take inventory on himself before he could fully commit to me, or anyone. As a result, no matter how much he liked me, he just couldn’t be in a relationship. So now, instead of hoping a guy would recognize a need to get help, I had a guy who was already doing so. Except I still lost out. Having to say goodbye was that much harder because AT LEAST he was taking the steps to get where he wanted to be. The last guy didn’t even know there were steps to take.

So although I tried to tell my new guy that he’s more together than he ever realized, and we’re too good of a team to not try to make a go of this, he felt that he just wasn’t good enough for me. (And attention Greg Behrendt: I promise this is not a case of “he’s just not that into you”). He was just so down on himself that in his mind, I’d be hurting myself by being with him. When I confessed that I really missed him and my days weren’t the same without him, he replied, ‘I hope things are going good for you. You truly deserve only the best, Jess.’ Just put a dagger through my heart right now why don’t you?

I don’t let myself open up too often, but when I do, I know (as well as my friends and family) that the person must be pretty special. Usually then my friends and family get scared as well. I’m at my most vulnerable, and there’s nothing they can do about it. As the rabbi said to us this year, ‘we’re all alive, but how many of us are actually living?’ So when I find someone that I deem worthy of me, I jump in with both feet, hoping for the best, but also, maybe pessimistically, expecting the worst.

I know I will get over the newest guy. My last relationship taught me that. But no matter what, when you’re going thru the deepest of heartaches, it feels as though you might as well be having open-heart surgery without the anesthetic.

Matters of the heart. Why does it have to hurt so badly?