For some odd reason I have never had a date during The Nine Days. Why this so, I am still unsure. Then again I am relatively certain that it’s not the only stretch of 9 days where I consistently have not had a date, such as Succos, so go figure? I can’t really complain; this shot, yet consistent, unexplained vacation has been sort of convenient. For one, that means less time dating while bearded. (Yes, I know, some girls like it! As concluded here, but as I mentioned earlier I don’t particularly like the itchiness that it provides, particularly on dates; it’s just a tad uncivilized, so yay for that.)
From a planning perspective, The Nine Days do not present any significant challenge. There are ample dairy restaurants scattered about that would make for a lovely outing as well as many activities that are somewhat appropriate, such as the Museum of Jewish Heritage and such. As for the weather…. We’ll I guess that’s not something truly unique to The Nine Days….
As an aside, and quite interestingly, it’s possible that if G-d were to send someone a really bad date during The Three Weeks or The Nine Days, they ought to be extra nice, as it might be a test in their adherence in compassion of bein adam l'chavero… or not… :-/
From a theoretical point of view, I assume, but do not know for a fact, that going out during The Nine Days is permissible, but does that mean that if one where to go out during these days that one shouldn’t do certain date activities? Should one abstain from “fun” dates and choose a more somber pastime? Should one limit the amount of corny jokes they make? :-p (Okay that last was just a tease…) But seriously, what is the right thing to do?