WALLACEWallace and Winona have an interesting relationship. In the manga, we see them together a few times, and Winona always seems a little bit awkward around him. When Ruby and Sapphire go diving to find the underwater cave, Wallace states that they can't wait around for them and they need to take action. Even though Winona is in charge, he gives out his own orders of what he is going to do, instead of talking to her about it. Then he demands to know what she is planning on doing. Instead of giving back an assertive answer she blushes and gets flustered, as if she doesn't know what to say back. To herself, she says what she really wants to do is join Wallace in on the battle, but she is loyal to the orders she was given. All of a sudden, a giant object flies at them and the two scream out, wondering what it is. The two end up okay, and realize it is time for them to split up. Wallace reaches his hand out towards her, she blushes and then grabs it once more. They touch hands to show their affection towards each other, just in case the mission goes sour and they don't end up surviving the battle.
We find out a bit of Wallace's past during the manga as well. When he finally beat the Pokemon League as a trainer, he turned down the position of Champion to take over the Sootopolis Gym after his master, Juan. It is also noted that this is the same time that Winona became a Gym Leader as well. He admitted to having the intention to stay closer to Winona, but she was opposed to his actions. She stated that she thought having a man much stronger around her would be smothering, which led her to break up their relationship. Back to modern day, Wallace attempts to fight off two villains, Archie and Max, but they taunt him and say to look closer to what he is fighting against. When he looks, he sees Winona, trapped and injured in in the middle of the battle field. With Winona held hostage, Archie and Max tell Wallace to put down his Poke Balls and surrender to them. Wallace is left with no choice but to listen to them, allowing himself to be defeated. However, Sapphire's Celebi ended up healing all of the fallen Gym Leaders, so Wallace and Winona were able to reunite together after the battle was over. The picture on the left shows Winona with both her arms on Wallace's shoulders. Could this imply that the two got back together from the life or death situation?! I would like to assume so!
I can understand why Winona broke things off with Wallace. She is a very powerful woman and likes to be in charge, therefore she felt intimidated by an even more powerful man in her life. However, she needed to realize that you can still be independent and be in love at the same time. Relationships aren't suppose to be smothering, and for her to assume that he would smother her was a bit unnecessary. But, if it was her first relationship, maybe she was just afraid of what it would become. I am glad that in the end, however, she realizes that she could't hold back her feelings for him anymore, and she embraces him with open arms (literally lol).