So, apropos of nothing in particular, let’s say you wish to communicate privately with someone you’ve not communicated with privately before, for whatever reason you might have. And, wanting to stand out from the crowd, you decide to try to be clever about it, because, hey, you are a clever person, and as far as you know, people seem to like that about you. So you write your clever bit and send it off, safe in the knowledge of your cleverosity, and confident that your various cleverations will make the impression you want to make on the intended cleveree.
Two things here.
1. The effectiveness of clever on other people is highly contingent on outside factors, over which you have no control and of which you may not have any knowledge; i.e., just because you intended to be clever doesn’t mean you will be perceived as clever, for all sorts of reasons.
2. The failure mode of clever is “asshole.”
Allow me to offer a suggestion. If you are privately communicating with someone for the first time, as a general rule, the best course of action is to be polite and to the point. This is particularly the case if the reason you’re communicating with that person is because you are hoping to get them to do something for you, i.e., you’re asking for the favor of their time and attention and even possibly their money. That is not a situation in which you want to risk the failure mode of clever.
This is not to say that your cleverness should not eventually come out in your private communication; there’s a time for it, and usually that time is after you’ve established enough rapport with the other person that you know their receptiveness to cleverness in general, and your brand of it in particular. It’s “third date” material, as it were, not “first date.”
Indeed, the most clever thing you can do with your cleverness is to know when is the right time to use it. When in doubt, don’t. And if you’re not in doubt, ask yourself if you should be, especially if you’re communicating privately with someone for the first time. It’s just a suggestion.