15 TV Heroines Who Suck At Picking The Right Guy

Television is supposed to be an escape, something that plays on the viewer’s emotions and fears. There is no question that women characters are sometimes both the butt of many jokes and the solid voice of reason.

There has been a surge of women writers in Hollywood as of late. They create strong women who still struggle with their choices in men. All these fabulous leading ladies can’t find a guy who isn’t a walking red flag. Here are 15 fantastic female TV characters who fail at picking the right guy.

15. Molly — Insecure

Anyone who watches Insecure knows that Molly, Issa’s best friend is a BBE — beautiful, black and educated. However, they also know that Molly is a hot mess. Her high standards and snotty attitude have put her in a category, where she is so far out there that she ends up picking the worst guy possible.

In season one, Molly was looking but she knew when a guy was not for her. Next, in season two, she seemed to be picking at straws and lowering her value. She has found herself in so many predicaments, fans question why she even bothers. Her latest conquest — getting involved with a childhood friend who’s married —  is just the icing on the cake.

14. Issa Rae — Insecure

Issa like Molly has had a hell of a time with the boys, which is beyond frustrating because she is a pretty smart chick. However, unlike Molly, Issa has no upper-class standard; she’s okay with a ghetto neighbor boy or a wannabe musician. She does not discriminate.

One has to wonder if she even has a bottom line. Issa cheats on Lawrence with someone who most would consider below Lawrence’s level. She begins a sexual relationship with her loser, stoner neighbor and she treats the good guys who want a real relationship like straight up crap. What’s her endgame? Are the fans missing something?

13. Marnie Michaels — Girls

Marnie is the absolute worst. Some may even say that after the way she has treated men in her past, she deserves to meet only losers and jerks. Within the entire series, the only “decent” guy she was involved with was Charlie. She managed to strip away his manhood episode by episode.

She made him look like a fool by cheating, lying, talking crap about her relationship, etc. Everything kind of went downhill from the get. Her other flings — Desi and Ray — were not step ups from Charlie. Nor are they steps down they are just… different.

Charlie had it together and they are kind of floated into an abyss. Marnie needs to just stop going for these artsy, path-to-nowhere dudes and grow up.

12. Mindy Lahiri — The Mindy Project

Since the beginning of the series, Dr. Mindy Lahiri has had way too many problems with men. She just never seems to notice that they are either using her for sex or they like the idea of a girlfriend — but just not her. One would assume that Mindy Kaling would write some better men into her show but maybe this is her way of keeping it real.

Truthfully, fans could have done without Brendan, judgemental Ben, that user Tom and of course freaking Tommy the liar and drug addict. Mindy now has a baby so hopefully, she’ll have better judgment when it comes to men. No one wants random men coming in and out of the lives of their children.

11. Carol Pewterschmidt — Family Guy

Lois’ sister’s escapades with men have been highly debated on Family Guy. Everyone in the family including Lois has made a joke or two about her struggles with men. She has been dumped time and time again. A whole episode was dedicated to her tribulations with love.

In it, she falls in love with Mayor Adam West, whom Lois tries to talk her out of marrying in a rush. Carol has so many last names that it’s hard not to laugh at her struggles in life. All these marriages, a kid no one ever sees, and nothing to show for it but an extremely long last name. Family Guy hit the nail on the head one more time.

10. Claire Fisher — Six Feet Under

Six Feet Under will forever go down as having one of the best finales in television history. However, one of the most annoying things about the show was Claire’s choice in men. She always seemed to hook up with guys that were just a little bit off. They were either blatantly not her type or their problems were way over her head.

And, the one time she did find a great guy, she decided to run off and “find herself.” The next time he appeared in her life though, she was willing and able. Before that, fans had to watch her suffer through narcissist Billy, art stealer Russell and of course that jerk Gabe, the toe sucker.

9. Jenny Schecter — The L Word

Jenny is a hot mess. Not only is she confused about how life works, she also lives in her own world. She thinks everyone wants to “understand” her. Truthfully, she is a horrible person who is easy to hate and to top it off, she picks horrible men who compliment her horribleness.

Okay, so some will say that Jenny is a lesbian — she’s actually bisexual — but let’s not forget that her fiancée for several years actually turned out to be a terrible guy. Then she dated Max who was transitioning from female to male. He was also a bit of a narcissist. Max’s hormone pills made him an even bigger jerk.

The only beautiful relationship she had was with Shane, her best friend. And that’s because she knew how to put Jenny in her place.

8. Louise – Pulling

Pulling is a British show about three friends trying to navigate their messy lives. They are all a bit messed up but Louise is the worst. She is cute and funny but — my lord! — her cluelessness when it comes to men is shocking.

Louise picks men based on their looks. Sure, everyone does this to an extent, but she is so desperate and sad that it never works out for her. She always sets her sights low and then cries to her girlfriends when the guys cheat on her, leave her, use her for a place to stay.

She’ll stick with bad men even if the sex is bad. Guess you have to kiss a few frogs before you find your prince. 

7. Sam Fox – Better Things

Not that she gives a crap but Sam Fox picks the worst men to hook up with. A single mother raising three daughters on the show Better Things, Sam refuses to get into relationships. Therefore, the majority of her encounters come off as friends with benefits or one night stands.

Right down to her ex-husband, who was a bonafide mistake. He never wants to hang out with their kids. He even had the audacity to ask her to keep the kids away from him during the summer so he could work on a project.

She keeps up relationships with unattainable men. But on the bright side, she knows what she is doing and doesn’t complain about being single. Maybe she’s onto something.

6. Dee Reynolds – It’s Always Sunny In Philadelphia

It’s not bad enough that sweet Dee has to deal with four horrible men in her life. She also has to be the girl who sucks at picking men and relationships. Since season one, she has been way over her head when it comes to guys. It’s like she’s so desperate that she can’t even see that there is something significantly wrong with all the dudes she chooses.

There was that guy from her acting class Darnell who was actually gay. To this day, she will swear up and down that he isn’t. There was the wannabe rapper who Dennis and gang convinced her was mentally challenged. And let’s not forget all the preppy douche bags she threw in the mix. Dee sure knows how to pick em’.

5. Buffy Summers – Buffy The Vampire Slayer

Buffy Summers is always on the tail end of a crappy relationship. In her case though, it’s not that the men themselves started out  crappy — it’s like she made them become crap. Well, except for that one childhood friend, who was using her to become a vampire.

Angel — her true love — wasn’t a bad guy. He was just so brooding that there is only so much one can take. Riley had his own demons — literally. Buffy just couldn’t catch a break. At one point, fans had to wonder is it the men or is it her? Not every guy can be messy, right?

4. Fiona Gallagher – Shameless

Fiona Gallagher is 100 per cent a product of her environment. She is noble for taking care of all of her siblings at such a young age. But it sucks that her only example of a man is her deadbeat, alcoholic father Frank. There is no doubt that she struggles to pick good men because she doesn’t know what a good man is.

Some say that Jimmy is the best thing that ever happened to her. But when you really examine their relationship, he was a terrible individual. He didn’t have an honest job, he was flake and a con man. Gus might have been the best man to stumble into her life but even he had his flaws. Besides, she cheated on him with her drug-addicted boss. 

3. Nancy Botwin – Weeds

Truthfully, Nancy Botwin should be number one on this list. Nancy knows what a good man is. After all, fans can assume that she was married to one based on flashbacks. She remembers her deceased husband, Judah, fondly.

However, after he passed away, it’s like she lost all her senses. Or maybe she never had any. She has managed to get involved with the most untrustworthy, drama-filled men ever.

She had some kind of weird relationship with her weed supplier Conrad. Then she got married Peter, a DEA agent — not the best choice. Then came a corrupt politician. The list goes on and on and truthfully, they were all a hot mess. Thank God, most of them died.

2. Olivia Pope – Scandal

How can one woman constantly pick the worst, most dangerous men? First, you’re having an affair with the President of the United States? That doesn’t seem like a red flag to you? Then in a bid to get over him, you begin dating a crazy ex-military type, who has so many of his own problems that he probably shouldn’t be anywhere near a relationship?

This one seemed to have been set up for failure from the start though. It’s like everytime Olivia gets into a fling, her father is behind the scenes either ruining it or setting it up to keep an eye on her. At this point how can she trust anyone?

1. Hannah Horvath – Girls

One can’t help but think that Hannah only gets crappy men because she is such a crappy person. However, it can’t all be her fault, right? The real question fans should be asking is what is making her pick up these guys? She comes from a good family, she’s a privileged girl, she seems to make the struggle herself.

She has been picking bad guys since college and — who knows — maybe before. A prime example is Elijah; how could she not tell that he was gay? Then there is Adam; he wasn’t a horrible guy, just kind of a lost cause. What does he really have to offer Hannah? She needed to get real and stop hooking up with people just because “it’s what girls her age do.”

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