Labels. We all know them: "Modern" "Yeshivish" "Frummie" "Velvie" "Srugi" "He's koveia itim" "She wears pants" etc. And of course, we all say we hate them - and we do. They put people in boxes, they essentially limit or define people into boxes when of course, nobody fits into that box. That's why every girl from Brooklyn still 'isn't the typical Brooklyn girl', and why every guy isn't really that "shtark". But we still all use them, because they're still 'useful' and they still help and they still allow us to get a basic idea of a person in a really short period of time, say... 60 seconds or less, because that's important, too. After all, if you need more than that to describe someone, there must be something wrong with them... right? End rant one.
But let's talk seriously for a second. Those annoying labels do matter, those characteristics we use to define people do have a use. When you're trying to set up a shidduch and you know that one side cares very much about following halacha strictly, it doesn't make sense to set them up with someone who doesn't. When one side cares strongly about specific chumros, even, it likely doesn't make much sense to set them up with someone who is very against those particular chumros. This is not a place for debate as to whether those chumros have great importance or are complete garbage; this is simply a common-sense approach to matching two people together. You wouldn't match up someone who is often extremely sarcastic with someone who doesn't appreciate or get sarcasm; you likely wouldn't set up someone who thrives when they're with someone who stays in the background and brings out their talents with someone who thrives on being at the center of attention. We all use common sense and our own gauges of what we think will 'work', and we try not to do the "oh, here's a girl, here's a guy, let's set them up" approach.
And that's all great. But what about when we start using those labels? Those labels are useful only when they actually have meaning. When someone says "Well, she wears pants...", that's generally used to define a person who doesn't follow halacha particularly stringently, does it not? So if a person is trying to set up a match for a nice frum young man who cares about halacha, and then they hear about the woman that "well, she wears pants", that's often going to cause the person to not even bother trying to set it up. And in most cases, that makes perfect sense. Why bother setting up a guy with a girl who doesn't particularly care about the halachos of tznius? It's simply a waste of time for everyone involved. He wants a girl who cares about the halachos; this girl does not.
But what about when those labels don't actually apply? What about a girl who does feel strongly about halacha; who thinks being tzanua is of utmost importance? What about a girl who specifically wears certain types of women's pants that she grew up learning were absolutely fine? What about a girl who knows more and cares more about halacha than most every girl you'll meet... but in this particular issue her understanding is slightly different than the "that's just what people do" approach? Is that a girl who shouldn't get set up with any halacha-following guy, because "well, she wears pants"? A girl who doesn't feel wearing pants is something she has to do, but something that as a single person following the halachos and minhagim she grew up with and learned - that's something that essentially results in her being "punished"? How does this make sense?
This is when labels cease to be useful and begin having real-life negative effects. Forget the specifics of the example above for a moment, and let's talk more generally. Instead of people consistently vetoing shidduch ideas before they even begin because people randomly throw out a few labels, let's think if those labels make sense in the specific case we're discussing. If the reasoning behind the label doesn't apply in the case at hand [such as pants = doesn't care about halacha], then don't use it. If it's a very specific issue that the person might care about, then why not let the people go out, date, and when the time is right to discuss the issue, they can discuss the issue themselves. They're mature adults, are they not? (If not, they shouldn't be dating!) If it's something within the realm of halacha regarding a specific issue that one may understand differently, let them go out and see if either side feels it's actually important; in the specific example above, perhaps the girl doesn't care that much about wearing pants if it's that important to the guy; or perhaps the guy is okay with it as long as it is within the realm of halacha. Let them see!
There seems to be this unspoken fear by people to set their friends up unless they think a person is 'perfect', lest their friend be 'insulted' that they set them up with a person 'like that'. That's ridiculous. Are we not all adults? If this issue was something that the person being set up cares about, then they can say "Thanks, but this issue is something I care about, just so you know for the future." And the person setting them up can respond, "Okay, good to know, I'll keep that in mind." Is that so difficult? Is that conversation so hard that people would rather look for any way to strike a shidduch through every label imaginable so they don't have to worry about their friend coming back upset? If the person is so horribly insulted by the suggestion, let them explain it. If they just want to whine, so don't set them up and you won't have to deal with it anymore. But don't continually strike ideas that seem pretty good because "maybe he/she doesn't want a girl/guy like that". That doesn't do anyone any good.
Shidduch crisis, eh. Whatever happened to not being so judgmental!?