While some people need alcohol to be themselves on a date, my friends joke that I probably need all my inhibitions to behave. If someone buys me an alcoholic beverage, he might get more than he bargained for. It will actually probably be fun, but once upon a time when a date got me a Jack and Coke, it emboldened me to break up with the fellow. I can't remember the details, but I'm sure it was probably in motion already at the time. Without the Jack I likely would have just discontinued the shidduch through the shadchan. (It was a beginning date. The discussion regarding communication and at what point you should break up in person rather than through a shadchan will follow.)
There are many different things to take into the equation regarding how to break-up. Personally, I feel like one of the worse things you can do is blindside someone. It's insensitive to take a girl on a long date, have a really nice time together, say nothing to her when dropping her off (or even tell her "I had a nice time") and then tell the shadchan you do not want to see her again.
Communication is super important to me. I will often have a conversation with a guy (after reaching a certain point in a shidduch) about how it's difficult to put ourselves out there and try to build a relationship when we know that either one of us can go back to the shadchan and end it any time. I find it's more helpful when trying to build a personal connection with someone to suggest that after this point there will a discussion about why it won't work if either of us decide to end it.
I know that not everyone dates like I do, and for some it's more comfortable to break-up through the shadchan. It can be more hurtful to hear it straight from someone rather than through a third party. However, because of this previously mentioned blindsiding problem, this is not always a good solution.
Generally the rule is that if you are communicating directly and have dropped the shadchan, you cannot go back to the shadchan and ask him/her to do your dirty work. It's also disrespectful to the person that you're dating. Even if you have not yet dropped the shadchan, perhaps it is still the right thing to let the other person know that you don't think things are going to work. It's a case by case thing, and you need to use your intuition.
Break-up speeches can also make or break the relationship. Be nice, be polite, and you don't have talk about every single thing you think went wrong. The shidduch might be over, but you don't have to ruin what you did have or walk away with a bad taste in your mouth. Sometimes it is helpful to discuss what doesn't work, because it will be beneficial to know why you won't want to revisit the idea in the future. Comprehensive break-up talks are also constructive in terms of closure. I'm all about closure, but I'll tackle that another time perhaps.
People often get paralyzed and don't know what to say when they're breaking-up with someone. One dude told me, "In all my dating I haven't met anyone who had the whole package like you, yada yada yada (a little elaboration here). I just don't think it'll work marriage-wise." After I told him I understood and no sweat, he started his speech all over again. I know he felt bad or perhaps stupid for walking away, but, really, why is it my job to placate you when you're breaking-up with me?!
Often people will go with the "It's not you, it's me," line, but that really means nothing. If you don't know what to say, try something sincere. I generally attempt to find something really great about the person and compliment him about it as a means to take the sting out of the breakup. Here's a depiction of how something like that would go: In our example, the guy I'm breaking up with is someone who's extremely refined and very sensitive. Maybe I appreciate this, maybe I don't, but either way, "You're really an amazing person, and I know the right girl will genuinely appreciate your refinement and sensitivity." In that sense I don't have to say that it's something I don't necessarily value, I compliment him on something I know he holds as something that's fundamental to who he is, and I give him hope for the future. Win win.
You obviously need to tweak the wording and the formula a bit to fit your situation, because breakup lines should not sound contrived. Canned lines are more of an insult than anything else. If you can't even speak from the heart to break-up with me, then was our relationship worth anything?
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