Poor Edith. She's probably had the worst luck of the bunch. She loved Patrick, but he was bethrothed to Mary and then he died. Edith then started a relationship with Sir Anthony Strallen, but Mary drove him away. Edith's fortune seemed to improve when Patrick showed up alive after all. Was he really Patrick or a fraud? That remains unclear, but Edith was left alone again when he left because of the family's doubts. Edith and Sir Anthony Strallen got back together and were even engaged. Edith was finally in love and getting married ... until Anthony left her at the altar. Yes, she's had terrible luck in love. And, it didn't get better from there. She started seeing Michael Gregson, a newspaper man, only to find out he was already married. He decided to go to Germany to get a divorce to marry Edith. Positive, right? Not really. He disappeared in Germany and Edith's now pregnant with his child from their one night together before he left.
Sarah had a troubled marriage with alcoholic rocker, Seth. They got divorced and Sarah moved to her parents with her two teenage kids. Her love life had its ups and downs. She dated a much younger Mark. They almost headed down the aisle, but it wasn't meant to be. She also dabbled with dating photographer, Hank. Sarah's started to find herself, so perhaps she's ready to for another relationship and commitment now.
Rebekah's troubled love life started early. She fell in love with and was set to marry Alexander, a vampire hunter. When he found out she was a vampire, he staked her and her brothers. Klaus killed Alexander and that was just the beginning of her brother's involvement in her love life. In New Orleans, Rebekah and Marcel fell in love and were happy until Klaus daggered Rebekah. She had a fun summer fling with Matt, but left hm behind when she returned to New Orleans. Her relationship with Marcel has been hot and cold since her return due to their loyalty to Klaus.
Matt's such a good guy, he should have girls all over him. Matt and Elena were the perfect couple until her parents died and she broke up with him. He got close with Caroline, but when she turned into a vampire their relationship soured. He had a whirlwind summer fling with Rebekah, but that ended when she headed to New Orleans. He needs to find a nice human girl that will love him for all he has to offer!
Sam's college girlfriend, Jessica, was killed on his ceiling like his mother. Her death hit Sam hard and set him on the road with Dean. He fell for Sarah Blake, but the job took him away. She ended up married with a daughter before she was killed by Crowley. Sam met Madison and they were instantly smitten. She ended up becoming a werewolf and Sam killed her at her request. Sam had an odd relationship with Ruby. She was his ally, his lover, his Demon blood supplier, and then foe. In the end, the brothers killed her. After Dean went missing, Sam finally found happiness with Amelia, but that was short-lived too when her presumed dead husband showed up alive. She ended up chosing Sam over her husband, but Sam had already left with Dean. Sam's love life has been filled with more death than happiness.
Dean's had more hook-ups than true relationships. He recognizes the limits that his job places on his love life. He has had a few meaningful loves though. Dean's best fit for a romance would have probably been Jo, since they were both hunters. They cared deeply about each other, but never were really together before she sacrificed herself. His longest relationship was with Lisa. She went from an occassional hook-up to his love. Dean lived with her and her son when he gave up the hunter life. He tried to maintain the relationship when her returned to the job, but it put them at risk. Dean's back to the occassional hook-up that's more fitting with his lifestyle.
Bay's the youngest of the group, but has suffered bad luck in the love department already. She fell for Ty and he left to serve in the Middle East. Then she started dating Emmett and he cheated on her with her former best friend. Ouch! When Ty returned from war, they gave a relationship a try and it was going well until was ordered back overseas for another tour. He let her believe that he cheated on her and broke her heart. May Bay find true love and honesty in her next relationship!
Captain Hook's love was killed by Rumplestiltskin. He spent years in anger and vowing to get revenge for her death. He finally put that anger aside after he met and fell for Emma. They kissed, but Emma's heart wasn't free. A curse separated them, but now they are back together only she doesn't remember him. Unrequited love....
Christopher was tricked into falling in love with and marrying Pamela without knowing she was Cliff Barnes' daughter. It got worse when she ended up pregnant with his children. His love life seemed to improve when he re-connected with his true love Elena. Their romance was upended when Elena helped protect her brother after finding out he set the explosion responsible for killing Christopher's twins. Will he ever find someone to love that will stand by side-by-side with him?
Bo's love life is naturally complicated by being a succubus, but she's tried to remain loyal in her relationships. Her main loves have been Dyson and Lauren. Both have been complicated. Dyson lost his love for her when he made a deal to save her. And, by the time he got it back, she had moved on to Lauren. Bo's relationship with Lauren went from a spy-bang to true love until the doctor took off and then went missing. Plus, it turned out that Lauren wasn't really Lauren at all, but Karen. They had a positive reunion, but that was soured when Lauren decided to stay with the Dark Fae over going with Bo. The succubus can't get catch a break when it comes to love. At least she always has her bestie, Kenzi, by her side!
Whether it's been a man or a woman that's caught Nolan's heart, he's been screwed over and betrayed. Marco revealed Nolcorp's ties to Grayson Global causing Nolan to lose his company. Nolan may have started out using Tyler, but he fell for the con man and it didn't end well. His relationship with Padma was filled with secret motives. Nolan ended up in jail because of a video confession that placed the blame on him. Most recently, Nolan made the mistake of falling for Victoria's son, Patrick. Yep, he betrayed Nolan too. Despite all the backstabbing, Nolan continues to have a huge heart and willing to give love a chance.