The only world that’s more complicated than the anime world is the world of love. Trying to find a life partner is tough. Even if one has good looks, it won’t help if they don’t say the right words. Flirting is usually the way most characters go when talking to their potential love interests. Some are successful in attracting droves of fans, and have an easier time in wooing the one they like.

On the other hand, there are plenty of anime characters who are just plain bad at flirting. It makes for a hilarious watch because of how bad they are and how their love interest rejects them. If they’re not facing rejection, their friends are probably dragging them away and telling them to calm down.

10 Brock (Pokemon)

Normally, Brock is like an older-brother figure in the group, and quite domestic. He sews and cooks for the group, making sure they get proper nutrition, and always has some Potions and Pokemon Food in stock. But as soon as he catches sight of a pretty girl, all common sense is out the window. His advances don’t really lead anywhere, and he’s rejected a good chunk of the time.

RELATED: Most Iconic Anime Pacifists

His love for Officer Jenny and Nurse Joy is so strong that he can tell when one is an imposter — and weirdly enough, this skill has come in handy throughout the series. Either way, the moment he starts falling heads over heels in love, his friends and sometimes his own Pokemon will drag him away.

9 Boa Hancock (One Piece)

It’s not that Boa Hancock is bad at flirting or seducing most people, but she just can’t seem to get Luffy to notice her. Then again, Luffy is a bit of an airhead, and being interested in girls is the last thing on his mind. However, Boa is so used to everyone falling for her that his rejection has literally caused her to faint.

But it can’t be denied that watching her flirt and try to seduce Luffy is pretty funny. He unknowingly makes her look bad whenever he doesn’t notice her advances, but this hasn’t stopped Boa from trying. If anything, his rejection has made her more determined to get him to notice her.

8 Loke/Leo (Fairy Tail)

Whether he’s in his human or Celestial form, Loke is a flirt no matter what. He is somewhat of a ladies' man and has had several girlfriends, but these interactions aren’t seen. When Lucy joined the Fairy Tail guild, he flirted with her until he learned she’s a Celestial Spirit Mage, then ran away stating they couldn’t be together. Though he avoided her for the most part, Loke still flirted with her whenever they did interact.

After regaining his Celestial powers, Loke would openly flirt and declare his love for Lucy, which was usually for comedic purposes. Lucy always turns him down or tells him to just stop, but she’s never cruel about it.

7 Mayune Awayuki (Pretear)

Mayune’s way of flirting and seducing men is rather unique and not a good way to start a relationship. She forced Hayate, Sasame, and Goh to make up for bumping into her (usually in hilarious fashion) by forcing them to be a butler. She would flirt with them while also coming up with a plan to seduce them, but they would usually end up leaving before she finished planning.

RELATED: Best Anime Stepsisters

Unfortunately, Mayune’s attempts to flirt with them are about as successful as her poor attempts to prank her stepsister Himeno. None of the Leafe Knights she tries to seduce give her the time of day, and most probably don’t even remember her.

6 Zenitsu Agatsuma (Demon Slayer)

Zenitsu fears he doesn’t have long to live because of his occupation as a Demon Slayer, so he feels he needs to find a wife soon. When Tanjiro first met him, he saw Zenitsu begging for a random village girl to marry him. At first, Zenitsu was pretty shameless in his wannabe-womanizing ways, flirting or showing off to any girl that gives him attention. Now, he has become more respectful when it comes to boundaries after Sumi, Kiyo, and Naho called him out on his behavior.

At the end of the day, Zenitsu's heart truly belongs to Nezuko Kamado. Every chance he gets, he flirts or interacts with Nezuko, even though she doesn’t really understand him.

5 Miroku (Inuyasha)

It is pretty well-known in the anime world that Miroku has the worst luck with the ladies. His way of flirting with women is by first asking them if they would bear his children. It's not exactly the best way to start off a relationship, and he’s usually rejected in hilarious fashion. It also doesn’t help that he can get a little handsy with them, especially Sango, who tends to be his most frequent target.

He usually ends up with a slap mark on his face and being scolded by Kagome and Sango, or Inuyasha and Shippo just shaking their heads at him. Granted, Miroku was cursed and believed he didn’t have long to live because of it, but asking a woman to bear his children is not the best opener.

4 Licht Bach (Plunderer)

To know Licht’s history with women, one just needs to look at his left hand. The poor guy has -999 on it, because that’s how many women have rejected him. It later goes down to -1000 after Hina tells him she hates him for leaving her behind. Poor Bach is actually a good guy, but he does come off very strong and a little perverted when flirting with ladies.

It probably doesn’t help that he wears funny-looking masks that usually make women avoid him. Licht has been able to make women fall for him whenever he removes the mask, since he is very good-looking, but he prefers to wear one when out in public.

3 Sanji (One Piece)

If there is one man in the Straw Hats Pirates the ladies can count on to protect them when needed, it’s Sanji. He claims that the main reason he joined the crew was because of Nami, and has consistently protected her throughout the series. He’ll flirt with her and sometimes Nico Robin any chance he gets, but he’s not too overbearing. Nami does use his attraction to her to manipulate him sometimes, but Sanji is fully aware that she does this.

RELATED: Most Iconic Royal Families In Anime

Whether Nami will return his feelings has yet to be seen, but it does provide some of the funniest moments in the show. Sanji could easily settle down with another woman, especially since he is of royal blood, but his heart seems to belong to Nami.

2 Jean Kirschtein (Attack On Titan: Junior High)

Jean likes to think himself as a ladies' man, but he most certainly isn’t. He likes to flirt and try to impress him, but they don’t find him attractive at all. If anything, they find Jean to be a little repulsive because of his arrogance and obnoxious nature. Even Marco told him that he’s just not as popular as he thinks, but Jean didn’t hear him.

The only girl that Jean has managed to impress is one that he doesn’t want. This is only because she’s a Titan, and fell in love with him because he threw his lunch at her. None of the human girls are interested in him and tend to stick with their own friends.

1 Ryunosuke Tanaka (Haikyuu!!)

Poor Tanaka has been ignored or turned down at just about every turn when it comes to his flirting with Kiyoko. He proposed to her the first time they met, but she turned him down without a second thought. This hasn’t stopped him though, and he continues to show his adoration for her and shares this interest with Nishinoya. The two of them protect her from men they think are flirting with her, even though Kiyoko is more than capable of taking care of herself.

Though Tanaka doesn’t stop his advances, he is pretty respectful about boundaries and just keeps it to harmless (albeit loud) flirting. He must have eventually done something right to make her say yes, because at the end of the manga, the two are married.

MORE: Dark Slice Of Life Anime