Holden met his ex-ex-ex-wife, Lily, when he was just her stable boy. They came from two different worlds, even if Holden's sister, Iva, is Lily's bio-mom (but it turned out that Iva was adopted). They thought their love could conquer all that, not to mention the brain injury that gave Holden amnesia, and Lily being so freaked out by her sister's death that she sometimes assumes her late sibling's identity.
But even after Holden became a successful executive, it wasn't enough to keep Lily from constantly rekindling the flames with Dusty, her first love. Holden decided he'd rather leave Lily and city life behind to live in the country and breed horses. Still doesn't stop him from kicking himself for not getting just how crazy Lily became after her sister's death ... until it was too late.
Holden loves all six of his kids and stepkids. (He and Lily both have kids from other relationships.) He was particularly supportive when son Luke came out of the closet. And, of course, Holden still loves Lily -- just not quite as much as he did any of the three times he married her.