Keep an Open Mind
You know your daughter may not have made the choices you would like to have seen her make, but she's getting there. To judge her negatively based on the fact that she forged her own trail instead of following a map that a certain father of hers tried to give her is unfair. Be aware of the common things that convince parents (wrongly) that their children are not now, nor will they ever be, adult enough to be married.
The Career Scene
You wanted her to go to law school, or at the very least, get her MBA. She could be making a killing on Wall Street, or she could be tearing witnesses up on the stand every day. Instead, she chose to work in a coffee house. Jeepers creepers, you think, did I teach her nothing about life? How's she going to make it on minimum wage?
Consider how difficult it was for her to not follow the path you laid out for her — the sure thing. She would, no doubt, be making a good living if she had gone to graduate school. Obviously, what matters more to her is achieving success on her own terms; she also wants to succeed doing something she enjoys.
Do you have any idea what her interests are? It could well be that she is planning on one day opening up her own little café or becoming a chef or a caterer, and this job is a stepping stone (and a learning experience) for her.
Think of it this way: Pick something that you do for fun or relaxation or simply because you're good at it. Is it the same thing you do for a living? If you could make money doing it, would you? If you were thirty years younger, would you take that shot?
Be honest. You'll see that she's not so silly after all. She might even know exactly what she's doing, and she might be the one laughing all the way to the bank someday.
Yes, she's brought home some doozies in the boyfriend department. There was that guy who was conducting a sensory-deprivation experiment and so chose not to open his eyes for the entire weekend; and then there was that other guy who was forever singing show tunes — loudly and off-key and at the most inappropriate moments (hey, he honestly thought that Aunt Betty's wake could use a little jazzing up). And what about the guy who was convinced that he was an illegitimate member of a certain royal family because of his uncanny resemblance to a particular prince? As you recall, he was off to Europe to claim his birthright…
So she's made some curious relationship choices in the past. That doesn't mean that
Yes, everyone knows that as the family patriarch, you know best, and your predictions usually come to fruition. Consider, though, that you may be a bit prejudiced, confusing your daughter's fiancé with those who have gone before. Give the guy a fair shake — it's what you'd want if you were in his shoes.
Her Support System
Your daughter is your baby — and not necessarily because you want it that way. She simply can't function without touching base with you or your wife several times a day; there's no way she can deal with life without you holding her hand. And now she says she's getting married. You can see it now: You'll be supporting her, her husband, and their kids.
Here's where letting go becomes your priority. If she's planning on getting married and leaving the nest, you have to help her to do it. Acknowledge that she's made a life-changing decision. As long as the boyfriend seems like a decent enough bloke, it's really all right for you to let go of the past and start thinking that she just may be headed for matrimonial bliss.
In any event, reminding her that she's never been able to make it on her own won't help matters and is not the helpful criticism that you might think it is. (In fact, it's just cruel.) This man in her life may be the self-esteem booster she's been needing all of these years, so don't assume the worst — help her to help herself. Be the strong, supportive (and if you can't say anything positive, silent) father of the bride.