Good question, in his twenties, he dated a lot and yes he was very picky. He did have one longterm relationship in his twenties though.

He settled last among our friends group. He is about 40 now. He has been married for about 5 years and before than he was with same girl for another 2-3 years.

His wife is a bit similar to him. Though I have never heard her complain about anything but art and literature are very important to both of them. Not just that they have very similar likes and dislikes. One major difference might be she is vegan and he is not. While every couple has their issues but, tbh, it seems they have fewer issues than average.

So it is like he found his soulmate and he is able to commit. (No kids yet.)