In his own warped way I think Henry loved all of his wives, except Anne of Cleves, but even after they got divorced I think there was a level of friendship toward her on his part.  Clever girl, giving him what he wanted 

Katherine of Aragon was his first love, and I believe they were in love for a while.  And of course, she never stopped loving him.  If she'd given him what he wanted – sons – they may never have got divorced.  I can see Henry, whilst taking mistresses from time to time, retaining a good level of respect for her and as long as Katherines position as queen and that of her child/children wasn't threatened she would have been content too.  A typical 16th century royal marriage.

Jane Seymour I think Henry chose because she was the complete opposite of Anne, but also I think he loved her more after she was dead perhaps more than when she was alive.  He must have felt something for her as it took him a good couple of years to marry again.

Katherine Howard he definitely loved or was majorly in lust with anyway.  Like Anne Boleyn she broke his heart and once a wife did that then Henry always reacted in the most extreme way possible.

Catherine Parr is interesting and in everything I've read about her and Henry, it was him who chose her simply because he fancied her.  I think the two were very well-suited and Henry actually grew to love her (although her being in love with someone else, perhaps her feeling towards him were more complicated!)  She could irritate him and he definitely tested her but then saved her at the last minute so I think there was absolutely a level of love there from Henry that never quite died.

But it was Anne Boleyn that Henry loved most passionately, obsessively and desperately.  She was the one who challenged him the most, the one who he would do absolutely anything for.  The grand passion of his life.  Not an exactly healthy love on Henrys part but it showed itself most obviously with Anne.  For the first time in his life he was absolutely head-over-heels in love.  But Henry could hate just as much as he could love… 

I agree with Sharon that Henry's love is conditional. I still have a hard time to accept that Henry was capable of loving anyone, other than himself.

It does seem Henry had a hard time telling if a woman was a virgin. Not sure what that says about Henry's..umm… abilities. I could say more, but I'll leave it there.

Katherine: first love of his life. Of course, the marriage was politically viable, but Katherine and Henry were equals in many ways. He trusted her to be Regent when away in France. Katherine loved Henry until the very end; Henry “loved” Katherine while she was fertile. When the possibility of sons ended, he moved on to a newer model.

Anne: Henry's obsession. She turned his world upside down. While it was a great love affair, it was not the healthiest of relationships. I do not doubt Anne's love for Henry, but Henry only wanted Anne was long as a son was necessary. This was the great passionate relationship of Henry's life. I imagine Anne haunted Henry until the end.

Jane: the perfect Tudor wife. She was Anne's antithesis. She was in the wrong place at the right time. I imagine Jane was terrified of Henry; Henry wanted a son, but I doubt he loved her. She was the rebound wife. He never respected or cared for her. It was in death that Jane became his true love. In life, she was a doormat for Henry's triviality and immaturity.

Anne of Cleves: the survivor. Henry fell for her portrait, and was disappointed when he met her in person. Another example of Henry's women never living up to HIS expectations. Although Anne was smart enough to know when to fold, and she earned Henry's affection and respect as his “sister.” She was lucky not to be “loved” by Henry.

Katherine Howard: the middle age crisis. Like many men, Henry fell for the young, pretty thing. He felt rejuvenated, young, and virile, but he was deluded to the reality of the situation. Poor Katherine having to endure sex with that disgusting man. I feel the most empathy for her. She got caught up in court politics she was incapable of understanding, and fell victim to a world she had no control in.

Katherine Parr. the nursemaid and friend. Katherine was a good match for Henry. While he was too late in life to have another passionate affair, KP was a passionate woman, who shared Henry's intellectual pursuits. She was smart enough to save her head, but was trusted by Henry when he made her Regent. She did her duty with intelligence and consideration. I think Henry needed a woman like her in his older years. I doubt she captured him like Anne or KOA, but she better treated than most.

I think Henry 'projected' what he wanted onto his wives. He didn't see the real women, only what he wanted to, whether good or bad. When he got to know the real women, he discovered they were not his imaginary ideal, but real human beings with faults and feelings like everyone else.

With Catherine of Aragon, I believe his love for her was conditional on her staying young and beautiful and producing heir's. She did neither, so forfeited his love. I can imagine Catherine as a mothering type of wife, who perhaps filled the gap his mother had left when she died.  Henry adored his mother, and looking at portraits of both women, they have similar features. I believe Henry also married her because she was the damsel in distress, he the gallant knight. He probably thought they would live happily ever after, but the reality was nothing like the fairy tale.

With Anne Boleyn, I feel Henry fell IN love. He loved her as a man, not a king. She was his intellectual equal, spirited, captivating and honest. I can imagine Catherine told Henry what he wanted to hear, where as Anne was brutal in her honesty. Anne was full of life, young and pretty. She was his great passion, and he loved her deeply, as she loved him. I imagine they were very close, living almost like husband and wife for a very long time (minus the marital relations). Once they married, he realised she was just a normal woman. She didn't give him a son, she was difficult, but he still loved her. I think he loved her till the day he died, but he believed she had been unfaithful, and had bewitched him.

I think Henry lost his ability to love before he murdered Anne Boleyn, she was his last love. Maybe something to do with the head injury, or just his humiliation of risking the love of his people, for an heir who never arrived. He believed he was the victim.

With Jane Seymour, she was easy to live with. He didn't love her, there didn't seem to be much to love. He lusted after he because he couldn't have her, and when he did, he treated her with disrespect. Once she gave him a son however, she earned his love. Unfortunately she died in the process. With Jane, Henry just wanted a woman who would shut up and give birth to sons. 

He didn't love Anne of Cleves – but he did project his 'ideal' onto her portrait. The reality was not how he imagined. He did find friendship with her.

Katherine Howard was his mid life crisis. After Anne of Cleves had shown him that he was no longer young and handsome, Katherine fed his ego. I think she may have reminded him of Anne Boleyn.

Katherine Parr was his companion and nurse, and he loved her as such.

I think Catherine of Aragon was actually his best-loved wife. She was the woman he loved as a young king, before he became the tyrant of later years. As such it was a purer love. Henry was the perfect medieval prince swooping in to rescue his perfect medieval princess, then later they became king and queen and would play Robin Hood in the palace. It’s adorable. They lived together for two decades, most of which time was spent happy. Then he symbolically graduated to the Renaissance, and his renaissance woman was Anne Boleyn.

Anne was the great passion of his life. He certainly was the love of her life. He turned the world upside down in order to possess her, but I don’t know how capable Henry was of actual love. I love Anne Boleyn and think she is one of the great figures of history regardless of Henry, so I don’t think I’m saying anything against her when I say she wasn’t Henry’s greatest love. I don’t believe love ever really dies, and there is some evidence of this with Catherine. Henry was cruel to her, but not as cruel as he was to subsequent wives. With Anne, there was passion instead of love, and passionate love quickly flipped to passionate hatred. He basically gave up on her, not caring if she were alive or dead, before she actually was dead. I don’t think he even began to think about her again until after Jane Seymour was dead.

With the others, I’d agree with the other poster who said Henry’s love was conditional. Jane gave a son, so she’s in, Henry loves her. Anne of Cleves-Henry’s in a bad mood when he meets her, so she’s out, no love. Katherine Howard-a lot of people are saying she was just his midlife fling, and I’m inclined to agree, but let’s not forget that contemporaries said at the time that she was actually Henry’s great love and her death hit him harder than the others.

Katherine Parr-in my mind it went something like this: Henry:”you know who was kinda hot? That girl Kate who you used to hang out with my daughter Mary. She seemed pretty sane too. Women these days are crazy. Maybe I’ll see if she’s not married maybe she’d like to come to court.”. I don’t really buy the idea of Katherine Parr as his nursemaid since Henry had doctors and stuff an probably wouldn’t want his wife to deal with his wounds. She seems more like someone Henry could reminisce about the old days with-he didn’t have Catherine of Aragon or Anne Boleyn to chat with in his old age, but he did have someone who was at court at the time as a teenager.

For me….Henry loved his ideas of each wife

KOA…Henry loved in the whole “courtly tradition”. He was her Shining Knight, KOA  the high born Damsel in Distress. His love was based on his protection and her suitibilty as his queen. She was regent while H8 was playing war in France.

AB…He fell hard for the unresponsive, distant, possibly heart-broken Anne. Wanting was much much more desirable than possessing. The fact the “The Whole World agin us” makes for strange bedfellows..plus young enough for healthy children

JS…presented as the Anti-Anne..soft, submissive, passive, easily moulded…the ideal Tudor Woman(®)…and from a fertile family…

AOC..lack of domestic replacement, many other royal ladies and their families had reason to be wary to Bluff Ole Hal.. Anne was really the only candidate. He was unprepared to love the reality of Anna.

KH..pushed as the “New Improved Howard…now 90% easier  on the King's psyche”…shame K wanted more outta life..like a young man or 2 or 3 or…

CP..twice widowed, used to dealng with irrisable men, shame she had a brain and was unafraid to use it.

For me, Henry had his illusions of each woman. That they failed to live up to them was the wives's fault.

Jane died at her trimupment moment and was viewed in retrospect as the “Perfect Wife'.

AOC  made the best of a bad deal and allowed herself to be cast off and as a result Henry respected her as he would have KOA should she have made the same decision.

CP outlived any reprecussions that Henry had in place, even though Gardinder tried..

KOA and AB failed to give Henry what he wanted…KH could have provided the “spare”

Sorry about the all-post purple.

I disagree with AoC being the only virgin Henry ever met…

With AoC I think Henry said she had saggy boobs and a podgy tummy. This made him come to the realisation that she had obviously had children… which as we know is not proof. I think he was looking for any reason to be disgusted by her, and found it there. Considering AoC thought she could be pregnant after a kiss, and lived a life away from men in her home land, it's pretty obvious she was a virgin.

Perhaps his behaviour explains his dislike of women after they had his children… He obviously liked toned ladies lol.