Top 10 Unlucky in Love TV Characters

“Stargate SG-1” (1997-2007)

A military astrophysicist always on the move, Samantha Carter is one of the smartest and toughest people in her fictional universe, but the life she’s chosen for herself definitely take its toll on her romantic endeavors. The majority of Carter’s love interests in the show tend to die, from her power-mad ex-fiancé to her brainwashed love interest Martouf - the latter of which she actually had to kill. Even when her love interests don’t die, she’s often left unhappy for years due to not being able to be with them, as was the case with the mutual attraction between her and commanding officer Jack O’Neill, given that their relationship would have been strictly against military regulations.

“Arrow” (2013-)

Being a billionaire playboy/vigilante ain’t all it’s cracked up to be. Oliver Queen, a.k.a. the Green Arrow, has endured more than his fair share of trials and hardships and (unfortunately for him) they often involve his love life. While his loved ones often find themselves targets of his enemies, Oliver has also fallen for villains, lost women he’s loved (some multiple times over), including the mother of his son. He may be out to save his city, but it’s arguably his love life that most often needs saving.

“Breaking Bad” (2008-13)

While other entries on this list may have more numerous instances of bad luck, Jesse Pinkman’s has a name: Walter White. His life might not have been great to begin with, but it went notably downhill when he teamed up with ex-teacher Walter White - taking his love life with it. He plans to run away with girlfriend Jane, but Walt’s inaction causes Jane to die of an overdose, for which Jesse blames himself. His next girlfriend Andrea has her son poisoned by Walt. Even after ending the relationship, Andrea is murdered by the men who’ve enslaved Jesse to be their meth cook.

“Smallville” (2001-10)

The man of steel may be bulletproof, but relationships are his kryptonite. Well, technically kryptonite is his kryptonite, but they’re a close second. “Smallville” explores Clark Kent’s youth, but he experiences more heartache throughout it than many do their whole lives, having not one but two of his girlfriends die, one of whom had also stalked and manipulated him. Then there’s his drama-filled romance with Lana, who marries his worst enemy and becomes literally toxic to him after absorbing certain green rocks’ radiation. Even his destined romance with Lois Lane isn’t without conflict, since he experiences the classic superhero love triangle involving himself, his love interest and his alter ego.

“Shameless” (2011-)

The Gallagher family as a whole is general pretty unlucky and dysfunctional when it comes to romance, but Debbie takes the cake. A dreamer whose fantasies border on the delusional, Debbie is generally sweet and kind-hearted, but her desperate desire for happiness, and boys, takes her to darkly criminal extremes, including losing her virginity by raping a drunk guy and then lying to her next boyfriend about being on birth control so she can get pregnant without his consent. Both of them rejecting her probably has more to do with her behavior than ill luck, but we couldn’t leave her off our list.

“The Good Place” (2016-)

Even being dead isn’t enough to stop a pratfall-laden love life. Chidi Anagonye is an incredibly nervous individual with near superhuman indecisiveness, which left him unable to form lasting relationships in life. Unfortunately, that same personality trait proves equally troublesome for him in the afterlife, as his alleged soulmate is almost completely the opposite of his own personality, and affection from two women sends him into a spiral. Worse, when he is finally decisive and open with his feelings, it’s all for naught, as he and Eleanor lose their memories soon after declaring their love for one another. If we were in his shoes, we’d have stomach aches too.

“Dexter” (2006-13)

Huh…another Deb! A homicide detective in Miami and the adopted sister of the titular serial killer of serial killers, Debra Morgan has an incredibly depressing and tragic track record when it comes to men. She’s been involved with married men, an older man, confidential informants, and even a serial killer - who turns out to be Dexter’s blood “brother” and who tries to kill her after proposing. Furthermore, she’s been involved with several other men who were murdered, one of them in front of her. Worst of all though is her brief epiphany that she’s in love with Dexter, which happens shortly before finding out he’s a serial killer. Talk about cursed!

“Supernatural” (2005-)

Over a dozen years of battling monsters and demons, and yet Sam Winchester can’t seem to catch a break when it comes to women, particularly since several of of his romantic interests are monsters and demons! Sam has gotten into relationships with werewolves, a demon, and several other creatures, and has even had to kill some of them. But the supernatural hunter’s luck isn’t much better with human women either, as his longtime girlfriend was murdered by a demon in the same way as his mother. Then there was that time a “normal” fangirl put him under a spell in an attempt to force him to marry her. Poor guy!

“Buffy the Vampire Slayer” (1996-2003)

Speaking of characters that attract supernatural love interests, Xander Harris might even beat our last entry. The sarcastic member of Buffy’s “Scooby Gang,” Xander experiences plenty of misfortune with his relationships, getting into a rather messy love triangle and later being sexually assaulted by the girl he had previously lost his virginity to. But where his bad luck truly shines is with monster women, which he attracts with strange regularity. His most lasting and healthy relationship is actually with a former demon, Anya, but even that relationship ends badly, since he leaves her at the altar because he’s afraid to commit. The fact that she’s killed a year later doesn’t help either.



Before we get to our top pick, here are a few honorable mentions:

Angela Montenegro

“Bones” (2005-17)



Shane McCutcheon

“The L Word” (2004-09)



Jane Rizzoli

“Rizzoli & Isles” (2010-16)

“How I Met Your Mother” (2005-14)

The protagonist of “How I Met Your Mother” endures quite a lot of heartbreak and unfortunate romantic circumstances before (and after) he meets the titular mother. While plenty of it is the result of his own choices, Ted dates his share of crazies, and he also has his heart broken several times, including being left at the altar. However, even meeting Tracy, the mother, isn’t enough to end his misfortune, as she dies during the finale, which is partly what spurs Ted to tell his story to his kids in the first place. Talk about a heartbreaking way to end a series.