[ryjm]

The article did not mention anything about skipping questions that were important to him; it specifically said that he had originally been picking questions "more or less" at random.

You're also assuming that the set of questions he had algorithmically selected did not overlap with the questions that were important to him. This seems unlikely.

The only dishonesty here is that by (presumably) determining the breadth and detail of his answers by order of importance to the cluster, he is in effect answering the questions /as if/ they are as important to him as they are to the average representative of that cluster. But if everyone else was also answering the questions "more or less" at random anyway ("He’d been approaching online matchmaking like any other user"), this doesn't seem so bad (and is probably why his algorithm gave him so many failed dates, since the relevant questions wouldn't have been answered).

Honestly all he did was make himself way more visible. You'd probably get a good amount of dates by making a sign and sitting in Central Park too. Sure, it's a bit distateful, but no less manipulative than that (and much more clever).