A few decades ago, I met my wife on a singles weekend. Then, singles weekends were the common way that people met. Granted, at the weekend, one of my friends suggested the idea of meeting this wonderful girl, so, in a sense it was a "shidduch" - match-making, but nowhere close to the formalized "shidduch" process we have now. We hit it off immediately and were engaged about 2 weeks after we met, and married 2 months later. Everyone thought we were crazy, and, a few tried to break us up. I won't delve into what eventually happened to most of the people that suggested the break up, but you can figure it out, probably.
While the idea of singles weekends is rare in the Orthodox Jewish community, and there are few mixed social events around, mainly because many community rabbis discourage mingling, I would still encourage boys and girls to meet informally rather than go through a shadchan (matchmaker). My reasoning:
- I've seen these shidduch "resumes" and "forms". Many of the questions are bizarre and the resumes are even stranger, frequently. "What color table cloth does your mom use on Shabbat?" - Why is that fact important to know BEFORE couples meet? Why is the shape, size, color and type of yarmulke important? I am surprised that often the one question that should be on a form for male applicants is "What occupation do you have?" or better "How do you plan to support your family?" isn't there at all. Do so many shadchanim expect mom and dad to support the newly married couple?
- I feel that match-makers interfere a bit too much in the process. Almost everything has to go through them. If I dated a nice girl and I want to date her again, I pick up the phone (and, yes, I mean using my voice - not text, fax or email) and I call her to ask. If she hesitates too much and can't give me a straight "yes" or "no" - well, what should I think? I think the answer should be obvious to someone who thinks it through. If I'm not sure, then maybe I'll get a mutual friend to pry some additional info from her. The point is, that the intermediary should be a back-up choice, not the main method.
- Personal meeting is, overall cheaper than using a match-making service or a dating service. Believe me, things add up quickly. But, besides the cost, the main advantage is that I think couples get to know each other's best when a spontaneous situation arises. If I meet a girl at an event or a weekend, we're both under a bit of pressure. IN a way that's an advantage, because we both get to discover how we can handle ourselves and have a conversation under pressure. If you want to stay married, believe me, both you and your spouse will be tested numerous times. This is a good way to discover each other. It's very different than when a match maker has prompted each of you on the rules and boundaries of what to say and what not to say.
Having mentioned some of these ideas, I am assuming that the two people already know proper etiquette. If not, hopefully, parents, siblings, peers, or friends would give each other some advice beforehand. A shadchan can do that, but, seriously, a shadchan's goal is ultimately to personally profit from the match making. Yes, they'll give you advice if needed, but, really - it's not the same as getting it from a close friend or parent who has known you well for a long time.
There are many who are shy or "awkward" and a shadchan may be the best route for them if they are uncomfortable going to events or single's weekends. I admit that blind dates and friend set-ups aren't for everyone. It really depends on the individual's personality.