There's no way that in a post that explores the limits of technology, he's actually trying to make some claim that he missed a huge red flag in an online dating algorithm's output, nor that we should interpret the situation in that way.
I wouldn't put so much stock in someone like eHarmony, but OkCupid--sure! Those guys use math!
disclaimer: I work for OkCupid Labs.
OKCupid uses reader-generated surveys.
Was somewhat disappointed when okCupid was acquired by match.com.
I agree with you that we shouldn't put too much stock in these algorithms. Still, it's interesting that OK Cupid reached the same conclusion as Alex's wife: we're too different.
The enemy part is particularly interesting because it indicates conflict. The story would seem different if it was like "Ok cupid says we're 70% match but we think we're 99% match!". Instead, it's OKCupid saying: "you have conflicts" and the couple deciding to move forward despite those conflicts.
I'm not trying to make a big point here; I just find this part of the story fascinating.