Did Anne Boleyn and Bessie Blount ever meet? Why didn’t Henry marry Bessie since it seems he was in love with her his whole life? And what do you presonally think, who was Henry’s true love: Anne, Mary Boleyn or Bessie?
There is no record of Anne and Bessie meeting but I'm sure they would have crossed paths at court at some point. Anne was in France while Bessie was Henry's mistress so they wouldn't have met until later, when Bessie was married to Gilbert Tailboys or her second husband, Edward Fiennes de Clinton.
I have not found any evidence to suggest that Henry was in love with Bessie his whole life. Bessie had a son by Henry - Henry Fitzroy, Duke of Richmond - in 1519 and possibly a daughter - Elizabeth Tailboys - in 1520 (see http://www.theanneboleynfiles.com/18102/was-elizabeth-tailboys-the-daughter-of-henry-viii-guest-post-by-elizabeth-norton/), but it does not seem to have a been a very long affair. It is impossible to know how the King felt about her. I think he was fond of her, after all, she had given him a son, but I believe it would be going too far to say she was his true love.
Henry would say that Jane Seymour was his true love, his one and only true wife, and I think that was because she gave him the ultimate gift, a son, and then died because of it. I think he then viewed her and their marriage with rose tinted spectacles. I think he loved Catherine of Aragon, Anne Boleyn, Jane Seymour, Catherine Howard and Catherine Parr in his own way at some point. He and Catherine of Aragon were married for over 20 years and he chose to marry her. His marriage to Anne Boleyn was a love match and he waited seven years to marry her, so he definitely felt strongly about her. He was devastated when Catherine Howard betrayed him and he seems to have been fond of "Kate" Parr. Who knows how he felt about Mary Boleyn? We don't have any details about their relationship, how long it lasted or anything. It could even have been a brief fling or one night stand. I would say that Anne Boleyn was his great passion, but only Henry knows.