I absolutely agree with you that the "incessant questioning" is more than irksome. I find it to be offensive in some cases. And as sites like End the Madness show, there is a huge emphasis placed on marriage within Judaism (specifically Orthodox Judaism) and it can come at a terrible price. The social pressure is intense. It can even become economic pressure; while I generally disapprove of anecdotal evidence, I personally spend hundreds more a month on rent than Harley, so that I can live on the UWS and hopefully meet my b'sheret (soulmate).
Yes, the pressure is ridiculous, and I don't necessarily think that the line of questioning is helpful (Really? We should get married? Thanks Mrs. Blum, now that you've mentioned it, I'm sure that he'll propose, he just hadn't thought of it yet.) but I'm not ready to throw out the baby with the bathwater. You see, I am a Modern Orthodox Jew, and I do see marriage as an objective good. I think that in a world where marriage exists, the choice to remain unmarried (for it is a choice) says something about the level of commitment in a relationship. I don't necessarily think that living with a significant other/partner is a good idea (aside from religious reasons), and I certainly don't think that those who live together first are more likely to stay married. The numbers* show that those who live together before marriage are 33% more likely to get divorced.
Unlike Harley and LT I do think that you can be objectively "ready for marriage." Even without a significant other in the picture, you are still not in a vacuum. I am currently in a financial and emotional place where I could look for a spouse. You see, I believe in "dating for marriage." The purpose of dating, in my mind, is to meet someone with whom I would want to spend the rest of my life, with whom I would want to build a strong Jewish family. I think that framing dating in that context changes it. When I say that I'm "ready for marriage" I don't mean tomorrow, I mean that I am ready to look seriously. Dating for marriage is a process by which you look for someone that you could love, respect, have fun with, etc, but also someone who shares your values. It doesn't have to be a perfect match, but it presumes two things, that I think are not necessarily present in non-dating-for-marriage contexts:
1) You recognize that marriage is work, you are looking for the best match (whatever that means) but you aren't with the person ONLY because you love them, but also because you think that you can make a go of it.
2) Marriage is a big step. You shouldn't take it just because it is the next step. So you've been dating for 4 years, you live together, the next step is marriage, should you get married? I don't think that everyone necessarily sees it as a seperate institution, and not just "the next step." When you look at marriage (a good marriage) as the goal, you put more thought into the process, really evaluate the person not only as a good relationship, but as a good marriage prospect.
So, yes, I am ready for marriage, and I want to get married, and I don't think that concubinage is necessarily to the detriment of the woman, or that living together is wrong. But I still resent when strangers, or even aquaintances feel the need to assume linearity in my relationships, and comment on it.
*Harley is going to kill me for saying "the numbers." I'll try to find a source.