I have amused myself while writing this book by trying to identify which, if any, late antique or early medieval writers (that is, those whose personality we can recapture, at any rate in part, with least mediation) I could imagine meeting with any real pleasure. It comes down to remarkably few: Theodoret of Cyrrhus, Gregory the Great, Einhard, maybe Braulio of Zaragoza -- and, with less enthusiasm, Augustine, for his remarkable intelligence and self-awareness however, not for his tolerance. But for all its distance from us, and in large part because of it, the early Middle Ages -- the many different early medieval realities -- are interesting.
I find this interesting because my reaction is almost the opposite: the late classical and early medieval period is precisely a Dinner Party Period. Lots of the major writers of the time would probably have been pretty pleasant to meet in person. Another Dinner Party Period would be the seventeenth and eighteenth centuries. This contrasts with, say, our time, which is not a Dinner Party Period; major writers and intellectuals today are often very boring people, who not uncommonly have clear social skills deficits. This is not really surprising, given that we live in a society that largely consists of people of relatively uneventful lives who do not study how to be charming dinner party guests. We still recognize that something like it is a useful skill, as when we talk about the importance of networking, but we have nothing like the elaborate customs, conventions, and expectations interwoven in even daily interactions that Dinner Party Periods do; we really leave it to natural talent and vague exhortation, and nothing more. In Dinner Party Periods being pleasant to know is a survival skill that can make the difference between wealth and poverty, life and death. If you don't have it, you either have to make important and useful connections some other way or you aren't going to be a major writer.
It's something of an irony, given that both the late classical/early medieval and the early modern periods are intensely polemical periods, whereas ours is not -- despite our occasionally thinking that we are fearsome, if you actually compare, we are quite mild and amateur polemicists, whose feelings are too easily hurt for us ever to be in a position to learn how to be really polemical. But I actually wonder if the two are related. Intensity of polemic is far more a matter of literary convention than an immediate function of personality. In highly polemical periods, people who are subjected to polemic tend not to complain about that in itself, because they actually expect it; they simply return in kind. It's just what you did in certain kinds of writing, and nobody was caught off guard by it; it was mostly just a genre thing, and you wrote in that genre in part just to show (as our much less polemical arguments-in-writing also tend to be done to show) that you could handle the language and style of argument as well or better than your opponent. There's no doubt that Sir Thomas More, a very intense polemicist, would generally have been awesome to meet in person, because the name-calling and the like would have been nearly entirely confined to the actual writing of polemic. And polemic itself is a genre that presupposes a society in which there is considerable rhetorical training, which historically is in itself treated as education in the ability to act appropriate given one's social role and situation. I'm pretty sure the reverse is not true, but I think it's an interesting possibility that in periods of intense polemic the people involved in polemic are actually very sociable -- in a sense your society has to be quite sociable to handle intense polemic as a matter of course.