Piper Halliwell and Leo Wyatt

The relationship between Piper Halliwell and Leo Wyatt is the longest running, and arguably the favorite among fans. Leo was first introduced as the handyman, and soon became a major love intrest for Piper. Piper and Leo's relationship has spanned the whole series, and has been the source of both extreme happiness, and extreme heartbreak for both of them.

Season 1
Sometime in 1998, the Elders gave Leo his biggest assignment yet--he was to be the Charmed Ones' Whitelighter. Since he couldn't tell the sisters just yet, he posed as a handyman. Both Piper and Phoebe showed interest in Leo, and it soon became a competiton for his attention. After Prue cast the truth spell, Piper took the opportunity to make a pass at Leo, and after asking him how he liked girls who made the first move, Piper boldly kissed him. When Leo became too close to Piper, the Elders sent him away; Whitelighters weren't allowed to be romantically involved with witches. He briefly returned to get the sisters in touch with Max Franklin, a young witch being tricked into using his powers to help a pair of crooks commit robberies. It was then that Phoebe found out he was a Whitelighter. Leo admitted he'd been agonizing over how to tell Piper he was a Whitelighter. After getting shot by a darklighter, Leo orbed himelf to the manor, where Prue and Phoebe were about to leave for a vacation. Piper was shocked and angry at the revelation of Leo being magical. Piper then successfully heals Leo by switching their powers. Leo then admits that he is willing to clip his wings for Piper's love, but Piper is unwilling. Leo then leaves the Piper to go back to the heavens, and their relationship is seemingly over.

Season 2
With Leo gone, Piper becomes involved with her neighbor Dan, but she and Leo still have feelings for each other. Leo fears that their relationship is getting in the way of their work, and briefly gives up his billet as the Charmed Ones' Whitelighter. After Piper gets sick with Oroya Fever, Leo goes behind the Elders backs to heal Piper. Leo subsequently temporarily loses his powers as a punishment, and Piper gives him a job and place to stay at P3. On Valentines Day, Leo gives Piper a card and flowers, and Piper has a daydream about running to kiss Leo, but she doesn't act on these feelings. It is later revealed their past lives were having an affair. Piper struggles with choosing between Leo and Dan, and after a spell goes awry, she reveals she loves Leo, and doesn't need a spell to tell her that. In Murphy's Luck, Piper decides she wants to tell Dan that she has chosen Leo, but he is out of town and wants to tell him in person. Piper finally breaks up with Dan in How to Make a Quilt Out of Americans. Piper and Leo have their first date as a new couple in Chick Flick, which is cut short by the elders. Leo starts staying at the Manor often, and starts to seemingly annoy Prue and Phoebe. Actually, her sisters both wish they has someone as great as Leo, and see him as the perfect man.

Season 3
In the beginning of season three, Piper and Leo defiantly try to marry in a handfasting ritual. Since a solar eclipse was occuring, the Elders couldn't look down to Earth to monitor Leo, but Cole, Phoebe's demonic love interest tipped off the Elders, which resulted in Leo being teleported back to the Heavens. Piper then goes on strike, vowing not to save a single innocent until the Elders bring Leo back to her. Finally, the Elders decided that if no innocents are put in danger because of the relationship, Piper and Leo can wed. Piper and Leo have a somewhat normal relationship until they once again attempt to get married. This time, it's Prue who stops the wedding, as her astral self takes over, and rides out of the manor on a motorcycle, destroying the wedding cake in the process. Shortly after, Piper and Leo finally have their dream wedding with their closest relatives and friends.

Season 4
Piper had very hard time after Prues death, but it all passed well thanks to Phoebe, Leo and new half-sister Paige. They were deciding on wether or not to have a child when Paige bought them a plastic baby. The fake child was hit by an energy ball, but Piper and Leo both decided that they could protect their child, and started trying for their baby. In last episode, when sisters were visited by an Angel of Destiny Piper found out that she was pregnant.

Season 5
Piper and Leo are expecting their first child in season 5, thinking they are having a daughter. They also begin to have couple issues as Piper is constantly annoyed with Leo's focus on his job and Leo is frustrated by Piper's pregnancy problems. To make them understand each other better, their unborn child swaps their powers and Piper's pregnancy symptons begin to occur on Leo's body. In mid-season, magic disappears from the entire world and Piper goes into labor, giving birth to Wyatt Matthew Halliwell, the future savior of the Earth. At the end of season 5, three Greek Titans are released from their prison and an unknown whitelighter from the future named Chris manipulates the situation into his own grip, turning Leo into an Elder and separating him from Piper. Leo and Piper share a painful goodbye, saying that they will always love each other. Leo tries to ease her pain to make it easier for her, right before Chris sends him to the isle of Valhalla.

Season 6
Without Leo to reverse the magic on Piper, she becomes increasingly "chipper" and optimistic, though her powers are out of control. The situation turns to the worse when Piper loses her memory, and they locate Leo on Valhalla. By seeing Leo again, her pain and memory returns immediately, but it becomes so painful for her that she joins the Valkyrie warriors to escape the torment. Phoebe and Paige manage to make her face the pain and Piper tries to move on with her life without Leo, though they remain in an odd relationship. Leo still cares for Piper, which is what keeps him from leaving her permanently. It is later revealed that Piper's new whitelighter, Chris, is actually her and Leo's future second son and that their first son Wyatt will become a powerful leader of evil in the future, but they must reconcile to conceive him. In mid-season, they are trapped in the Ghostly Plane where their powers are numbed, and Leo gets poisoned with whitelighter poison. Through this incident, they lower their guard and make love, thus conceives Chris. Leo later decides to leave Piper and Wyatt permanently to keep them safe. Finding out that she is pregnant, she decides to keep Leo in the dark about it.

Six months later, Piper becomes the target of a spider demon and Leo is asked to help, which forces him to face the fact that she is pregnant and that Chris is really his second son. They become closer again after this as Leo decides to stay with them for the time being to keep them safe.

By the end of the season, elder and headmaster of Magic School, Gideon, attempts to sacrifice their son Wyatt because he believes that a child born with such powerful gifts will become corrupted overtime, without knowing that he is the cause. Piper goes into life-threatening labor while Leo goes to stop Gideon, but also loses Chris in the process. At the end of the season, Piper is saved and baby Chris is born perfectly healthy.

Season 7
Two months have passed since the end of season six, but things haven't gone well for Piper or Leo. Piper has completely cooped up in the house with her children and Leo is crazed to seek vengeance on the demon, Barbas who helped Gideon. Phoebe persuades them to attend an Indian wedding of their friend's, only to get hijacked by the Hindu gods, Shakti and Shiva. Barbas attempts to make Leo kill another Elder by going after Chris, and lure him into a trap. His plan is a success, but Piper and Leo decide to keep it hidden. Leo, being emotionally distraught, has an incredibly hard time readjusting his life on Earth as he is haunted by "weird faces".

Season 8
Last season, Leo and attacked by the Angel of Death. The sisters are looking for a way to reverse the situation. Piper calls for an Elder and an Avatar to restore life to Leo, but both were forbidden to do so. So, the sisters called the Angel of Destiny, who warned of an impending evil force and that Leo's death would be the only motivation for the sisters struggle with that force. They decided to freeze Leo promising if they beat the Force he returned to them.

After the destruction of the mansion and the deaths of Phoebe, Paige, and Christy Jenkins, Leo returned by the Angel of Destiny. If not intervened, Piper would have killed Billie Jenkins, in an act of revenge. With the manor destroyed, Piper and Leo leave the area.

Piper and Leo went back to the past to save Phoebe and Paige, which they do successfully. On their trip, they accidentally travel fifty years in the future, where they meet a happy, much older, version of themselves.

The Future
It was shown 50 years into the future Piper and Leo are still together and had 9 grandchildren. it is unknown how many fights they may have had to this point but it is shown that they are still in love.