Also, here's my .02 re-posted from the comments section:
Rather than answer the questions that were important to him he decided to find a set of people he thought he would like then only answer the questions they care about, and not even the way he would naturally answer them, rather he used an algorithm to determine the weight that would be best to get the highest match %. The fact of the matter is he could've spent a fraction of the time just answering all the questions honestly and with his honest weights and he would've found high matches too. Furthermore, he could've narrowed it down to just the kind of people he wanted through a normal search and then filter their questions based on what's important to them (which is a normal question filter on OkCupid).
So in fact what he did was pretty bad, violates OkCupid's TOS in numerous ways and at the end of the day wasn't honest to himself as he created specific profiles for his targets.
Honestly, we should not be celebrating this.
To recap what he did:
1. Didn't want to answer questions, so let's find all the questions that are important to everybody from the categories of people he thinks he likes based on clustering and then browsing a profile or two of people in that cluster. (He did this by creating numerous fake profiles and having those bots answer all the questions so he could scrape his targets question)
3. Create specific profile for his targeted group. With words and information that he knew they would like.
2. Answer ONLY the set of questions deemed important to those people. He answered these with weights determined by an algorithm that determined the best weight to achieve the highest match% rather than honestly.
3. WIth new found 99% matches go on dates with these people and follow normal dating process.
Now that we see the above broken down we can see that it's really not good. In fact, he was only answering what they wanted, and created profiles for them. But he wasn't being honest with himself or with his answers. If we're trying to match with everyone, which is essentially what he did, it's not that difficult to do. The fact that he eventually found someone is great, but the information used was faulty. Obviously there's no way he would be 99% with that many people normally.