The context obviously makes a big difference here. If the situation is one in which you have only just met the person and you're operating on a superficial level, or there was little to no connection/chemistry, neither is probably that difficult. Sure, you may feel bad if the other person had feelings for you, and/or was very positive about the shidduch, but at the end of the day, it's just not that hard to say goodbye to someone you shared little with. (If there is hurt here, it would be the losing what the shidduch represented rather than the person himself/herself.)
In cases of longer stints, if you know that someone likes you and you don't like him/her, it may be harder to be the heartbreaker, because if the other party ends things, you probably won't be that broken up. On the flip-side of that, if you like someone and s/he doesn't like you, I'm not sure which would be harder. You almost don't want the person to continue dating you if you know s/he's not into it, so you might rather him/her break it off, but maybe it gives you a sense of empowerment to be the one to call it quits.
I was once dating someone, and things were a bit ambiguous. We got along great, but we had some major hashkafa questions. When push came to shove, because we weren't sure about things, he decided that was enough of a reason to break up. (I should mention that he was happy to continue dating forever, but I sort of forced his hand by inquiring what we were "up to" and wanting a direction/tachlis for our dating.) He suggested we take a break (indefinitely), in other words, break up and keep the option open of revisiting things. (Tangentially, revisiting is always an option, regardless if you outline that when you part ways or not. It makes things harder when you do say it, because you then keep this person in the back of your mind, and it's harder to move on. But maybe that's just me and my need for closure.) Either way, ultimately, he made me feel like I was breaking up with him, or at the very least like it was mutual. I think he thought he was being nice by giving me that empowerment.
When you find yourself in a serious relationship in which both of you thought things were going somewhere, this is obviously the most difficult scenario. If you break things off, you may end up feeling really awful about what you did to the other person, second guessing your decision, feeling like you created your own unhappiness, or a whole slew of other emotional repercussions. In this case being the heartbreaker still leaves you heartbroken. The other side of that coin is feeling jilted and angry. However, that anger is almost better than just the lonely sad and perhaps guilty feeling of scenario one.
In one of my serious relationships, I called it quits at the end of round one. I remember feeling really bad about it for awhile afterward. At the end of round two, he ended up picking up that break-up, although we both agreed marriage was not in the cards for us, and the break-up was mutual. I guess we were just not in agreement when the break-up should happen, or maybe it was the fact that he was engaged a little over two months later. He was good about making sure we were both ready to part ways and move on, had the clarity and closure we both needed, but still I think I felt differently than round one.
For sure in the scenario with the dude I was almost engaged to, in which he changed his mind out of the blue refusing to give any explanation and then got engaged five weeks later, anger helped me there. Had I listened to all the pink/red flags and been the one to break up with him instead of the other way around, I think it would have taken me a lot longer to get over him than it did this way.
Bottomline, break-ups are difficult no matter which way they break. So, please remember a little break-up etiquette.
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