I started off posting this as a comment over at A Blob of Something Different in response to this post, but then it got so long that I figured I'd just post it on my own blog. It's an old post, but I'm sort of new to the blog, so I hope to be forgiven for my delayed reaction.
I married at 19. I was lucky. I never had to shidduch date because my husband and I were close friends and never dated at all. But had I not been in that position, I wouldn't have felt ready for marriage for a very long time. In fact, in the weeks leading up to my wedding, I felt EXTREMELY unprepared for marriage. Terrified of it, even. I remember calling up my best friend in tears on multiple occasions asking her if I was making a huge mistake. In the months following my marriage, as my husband and I went through the normal adjustments that newlyweds must endure, I questioned my readiness some more. Thank G-d, I DID make the right choice, and clearly I WAS ready for marriage because we've been mature enough to get through the growing pains and ups and downs that wedded bliss inevitably entails (I say "we" but the truth is, I think it's all Yaakov. Ask him about my use of the "reverse royal We" in other contexts, like chores).
All of that being said, I will state the obvious: Pressuring 18-19 year old girls to marry, out of fear that they will become old maids at 21, has resulted in a lot (this being the scientific measure of choice for such precise statements) of failed and unhappy marriages, or broken engagements (if they're lucky). Obviously MANY happy marriages have also come out of this (I would even say that MOST of these girls end up happy). But we should never push aside the concerns of a girl who doesn't feel ready.
On the other hand, we really can't blindly accept it, either. It's important to find out WHY the girl doesn't feel ready. It may be something vague and difficult to put in words, or it may be something specific. In either case, there are a lot of valid reasons why a girl may feel unprepared, but that doesn't mean she should just sit and wait for them to resolve themselves. If she says, "It's really important to me to finish college first" and she's actively working towards that goal, then wonderful. But if she feels that she doesn't know herself well enough and is simply waiting for an epiphany to hit, we have a problem.
I may be biased because I'm a social worker in training, but I think therapy is an extremely useful tool for just about everyone, not just the so-called "damaged goods" among us. That's not to say that everyone should always be in therapy, but I believe that there comes a time in every person's life where they would benefit from a therapy relationship. It's my personal opinion that shadchanim should recommend therapy to young men and women submitting their resumes. Shidduch dating is an emotionally turbulent experience, and it can be helpful to have someone impartial to help you process everything that's going on. Obviously, there are those who have enough support from friends and family that this may be unnecessary, but I think they represent a minority of very lucky people.
And while I don't believe that a girl who feels unready for shidduchim is "sick", I do believe that such a girl may benefit from having someone who can help her work through those feelings. So while it shouldn't be about "convincing" her to be ready, I think it is important to offer her support so that she can resolve whatever concern may be holding her back.
Now I'm fully aware that in the shidduch world, the word "therapy" can become a stigma and, as a result, many in the community have developed a phobia of entering into such a relationship. But that, my friends, is another post.