The Handsome Lech is a skirt chaser even if his shameless flirting is playful and kind of charming. When the more negative parts of their personality become obvious (fear of commitment, irresponsibility, etc.) this will drive away potential suitors. Everyone else will merely not take him seriously because he's a good guy at heart.
These are almost guaranteed to have luck with the one character (who is attracted to him, if only in a Slap-Slap-Kiss way) willing to put up with these problems. If not, then Failure Is the Only Option.
This may be the quirk of a Bunny-Ears Lawyer. Compare Chivalrous Pervert, with which this may overlap. A Casanova Wannabe with the added bonus of being attractive. Unfortunately, this may not apply to the rest of their personality.
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Anime and Manga
Genpou Saji from Ikki Tousen. His introduction is groping Hakufu (which was also the first time they met and stole her magatama), sleeps with Ryoufu and uses this to turn her against Toutaku (and may have raped her, according to the Battle VixensMacekre manga), teases the Tsundere Ryoumou (who's in love with him) mercilessly, fingers a nurse when he's hospitalized, much to Ryoumou's anger, makes Ryuubi (who's the leader of another warrior group) almost cry by groping her Gag Boobs in Dragon Destiny, which was the first time they ever met...
Oreldo from Pumpkin Scissors fits the bill perfectly, has the looks, and doesn't need a library card to check the "file folders" in the records office(the records keeping girl is hot, and the only obstacle keeping him from important information). He is also well known for showing up in the series with dishevelled uniform and lipstick on him.
Miroku in InuYasha is infamous for his smooth if perverted behavior of groping women and casually asking them to bear his children. See here under "Miroku Promo". Further supported in that he stops almost entirely once he finally gets around to proposing to Sango. The key word in that sentence being almost. Hilarious in that when, with eyes sparkling, she asks him, "Does this mean you'll stop womanizing?" he answers with a confused, "huh?" and then dons a pained expression.
Gojyo from Saiyuki - with his long red hair and smooth talk come ons whenever the group stops anywhere populated. Always garnering severe upbraiding by Sanzo ("lecherous bastard"); or ridicule from Goku ("pervy kappa").
Tatewaki Kuno from Ranma ½ - very handsome, rich, excellent vocabulary, and apparently a figure well-skilled in the arts of polite romance. He's also so incredibly egotistic that he can't conceive of the idea of a girl not being attracted to him, as well as being willing to glomp the girls he is interested in at a moment's notice and also something of a hypocrite who is capable of such feats as ranting about how mixed bathing is for "moral degenerates" while racing eagerly for the baths with a girl in his arms. He isn't much of a playa compared to Mikado Sanzenin from the same manga/anime, whose very name is a pun in Japanese meaning "sex-obsessed neurotic" and who openly boasts of his plan to have kissed over 1000 girls — Kuno is simply fixated on two girls at once ( he thinksone is a girl) and openly proclaims that he will date them both at the same time, because he can't bear to choose either one.
Kurz Weber from Full Metal Panic! often gets slapped around by the female series leads for lecherous behavior.
Kaji in Neon Genesis Evangelion frustrates Misato by disappearing at the worst times and flirting with other women to make her jealous.
El-Hazard: The Magnificent World: Alielle's lover, Princess Fatora is a handsome lech throughout, albeit a very ineffectual one since she never gets the women she chases after.
Shizuru of Mai-Otome. Despite being in love with her client, Natsuki, she will playfully flirt with other girls from time to time whenever she gets a chance (witness her exchanges with Arika in a few early episodes). "Bewitching Smile", indeed.
Straight Cougar's constant failures when hitting on Mimori in s-CRY-ed, mainly because he forgets people's names.
Nagare Akatsuki in Martian Successor Nadesico, while having the looks and personality of a playboy, has no luck with any of the women on the titular battleship.
One might argue that Roger Smith from The Big O fits into this category, due to his openly-acknowledged prejudice in favor of beautiful young women; in fact, Dorothy calls him a "louse" on several occasions, but for the most part Roger manages to behave himself fairly well.
Sanji from One Piece is an odd case as he was originally presented in this manner, finding plenty of women (not including Nami) who found him attractive, but later on he became a combination Casanova Wannabe and Butt Monkey as all of his advances became universally rejected and often met with physical abuse. In Fishman Island arc, the mermaids are pretty enthralled with him.
Gundam 00: Lyle Dylandy explots this trope. aka the second Lockon StratosHe acts the part towards both his teammate Tieria (praising his beauty and nicknaming him "Mr. Cute Instructor" in episode 3) and ex Emotionless Girl Feldt Grace (stealing a kiss from her and getting slapped for that, in episode 4). However, lechery plays less of a part than you'd think; this is a small plan from the guy, destined to have them see less as a Replacement Goldfish for his deceased twin brother Neil, the local Big Brother Mentorand the first Lockon, who played an important part in Tieria's and Feldt' lives.
Soul Eater: Spirit's behaviour cost him his marriage and his daughter's respect but he still flirts with anything in a skirt. It's revealed later in the manga that despite being a regular at a local host club, all he does is talk about Maka and her mother. That's it. Every. Single. Time.
Rosario + Vampire's werewolf Gin. He's pretty, even if he does have girls sticking posters in high places just so he has a chance to look up their miniskirts. He's even prone to groping girls while he's having a casual conversation with them!
Albireo Imma in Mahou Sensei Negima! straddles the line between this and Loveable Sex Maniac; he's handsome enough to have little difficulty with women, but most turn away due to his 'subtly directly subtle' technique - he'd have you believe he's a Chivalrous Pervert, but he'll smile a smile you know you can't trust, act politely as he can deceive, then do something perverted enough to surprise even resident Dirty Old Ermine Chamo.
Baccano!: Claire Stanfield, as he confesses to Rachel, has never so much has gotten beyond a second date with a woman. It's not because he's unattractive (he isn't), or because he's crazy (He is, but they didn't know that), but rather -as it turns out- because he's very, very forward and insists on heading straight to the altar without so much as knowing the girl's name. He insists that Chane is different (beyond the fact that she didn't immediately reject him) but his longtime buddies are more than a little skeptical.
Luck: Wait, you didn't propose to stranger again, did you?
Claire: Something like that...
Daisuke Misumi in Chaos;Head. All his conversations with Takumi either start with or contain at least one mention of a girl he's chasing.
Gold from Pokémon Special was this during the Johto arc at times - at one point he even smacked Blue on the ass teasingly. Silver was not amused. By the time the Emerald arc rolled around, he had gotten over it.
France from Axis Powers Hetalia, going after male or female. However, in Hetalia Bloodshed 2010, it seems Kitty!America from the parallel world takes up this role, seen when he kidnaps a very drunk China and Hong Kong and forces them to wear cute, skimpy outfits.
Naruto: Jiraiya is considered a Handsome Lech, and a self-proclaimed Super Pervert. Despite this, he was shown with beautiful women on his arms several times, and even got Tsunade to fall for him. His apprentice, Naruto, seems to be picking up the slack.
8th Grade rookie football player Kouta in Area no Kishi is known for his skirt chasing tendencies, often finding him on the receiving end Armor-Piercing Slap, Megaton Punch, or being buried up to his shoulders in the ground (and usually buried head first, at that.)
Frau from 07 Ghost. Porn conisseur, incorrigible flirt and occasional patron of some sketchy establishments. He's also a Bishop in the Church.
Cross Marian of D.Gray-Man. He likes women in general, and even comments only women interest him. He's got quite a few lovers. It's assumed majority of Cross' lovers are prostitutes, since his hobby is visiting brothels. When they get with him, they are apparently crazy about him, since it's hinted he's a caring man, as he drops the Jerkass Facade when he's alone with women, and they take care of him, as we hear from Allen, and see with Anita. However, his open women-loving tends to be a turnoff for some higher principled women. Klaud, a higher principle women shows no interest in his advances at all. He Cross flirts with lenalee, a young girl but, she's indifferent to him in general, and openly tells him his sweet talk won't get him anywhere with her. So, he's not a bad man, and does care about his lovers once he finally gets with them. Some don't get past his heavy flirting to see that and give him a chance, as it seems to be the case with Klaud.
Though any male main character that has an affair in Gankutsuou could fit the description, Andrea Calvacanti wins an honorable mention because of his antics with Hermine and Eugenie Danglars, considering they are his mother and sister.
Aquaman became like this after being de-aged to his teens by an evil witch (boy). "Hey, baby. Wanna get wet?" This stood starkly in contrast with his then-current Darker and Edgier look and characterization, making it all the funnier.
This is Prince Charming's power in Fables. He is supernaturally attractive and has pointed out that when he sets his sights on something he always gets it (this works with more than women). Naturally Charming is hollow and emotionally cold inside. However, the fact that he managed to wake the Sleeping Beauty with his kiss proves that he truly loved her that moment. His problem is that his True Love has absolutely no staying power, shifting from one woman to another at moment's notice.
Woody from Quantum and Woody, who thinks nothing of flirting with a cute girl while in the middle of a hostage situation... even after he shoots her.
Woody: "So, hey, I'm Woody. Maybe I can call you sometime—"
Hostage: "—?! You shot me—?!"
Woody: "So, what, meet for drinks, then—?"
Commander Rawne in Tiberium Wars is an unabashed skirt chaser whose tendencies are regularly called out, and aren't overlooked by his superiors; at one point, General Killian Qatar "bribes" him by giving him a billet in a mostly-female barracks. At another point int he story, he grants a wounded female soldier high-priority and expensive medical treatments and replacements for her damaged eyes, and the scene implies the entire reason he did so was because he found her attractive.
Paris is said to have been this trope before he met Helen in Chance Encounter II. Later in the series, during an unfortunate incident involving Legolas, an evil, power hungry Cardinal from the 12th century, a poisoned arrow, a Maiar with healing abilities, Legolas gains the ability to (temporarily, thank God) read minds such as Will (who is contemplating what he is going to do to Elizabeth when they get home) and Paris, who Legolas claims, 'has extensive knowledge of all matters carnal".
Chow from Wong Kar Wai's 2046. He's handsome, always ready with a charming smile or a flirtatious compliment, and is never without a woman on his arm or a conquest to chase. The truth is that he uses his charm to keep women at a distance because he already lost the woman he truly loves.
York from Days of Being Wild qualifies as well. The main difference between him and Chow, however, is that Chow's past makes him at least sympathetic, whereas York comes off as a self-absorbed jerkass.
Star Trek (2009). Kirk lusts after every woman in the vicinity (even when being dragged through Sickbay by McCoy, sick as a dog from anaphylactic shock) but the only woman with whom he (visibly) scores (almost, at least) is Uhura's Really Gets AroundGreen-Skinned Space Babenote an Orion slave girl — emancipated, we assume. roommate (see below, under Live-Action Television regarding how Kirk was portrayed in TOS). Federation society as portrayed on Earth and within Star Fleet within the Reboot was realized as the sexually conservative form found in previous iterations.note Note the traditional gender roles in the bar scene, in which Uhura tried to wave off "Cupcake" (and failed) when Kirk was flirting with her. Whether or not Starfleet's sexually opened society remains an Informed Attributenote out of necessity, with today's MPAA. or has intentionally been retooled out, (without Roddenberry around to veto such a change) remains to be seen in future sequels.
Peter O'Toole plays one in What's New, Pussycat?, but tries to overcome it through psychoanalysis for the sake of his impending marriage. Unfortunately his analyst (Peter Sellers) is something of a Casanova Wannabe and little help.
Daniel Cleaver from Bridget Jones' Diary, played by Hugh Grant who moved into this type of character once he got too old for the standard romcom hero. He's an attractive boss who starts an Office Romance with Bridget but he makes it clear the strings are not quite attached. He cheats on her, and was cheating with Bridget on his fiancée (who presumably knew about Bridget and okayed it). He later gets dumped by said fiancée and begs Bridget to take him back, feeling she's the only one who could make him better. It's also revealed he slept with a young wife of his (former) best friend.
Will (Hugh Grant) from About a Boy. He's a terrible womanizer. He realizes that single hot moms are the best kind of women he can get lucky with because they have unresolved relationships and they break it off — so he gets laid, an easy break-up and he needn't feel guilty. When he finally finds a woman he would also want to talk to, he finds out he has nothing to talk about. He's that shallow. He's friends with this lonely kid, and he talks about him.
Ciaphas Cain, HERO OF THE IMPERIUM!, openly admits in his memoirs that he has (ab)used his prestige to enjoy the favors of high-ranking officials — specifically, their wine cellars and their daughters (or at least he did before he met Inquisitor Vail and possibly afterward, too).
Howl from Howl's Moving Castle. He's proud of the title as it gives him a bad reputation and less work from the King. Howl falls for Sophie the first time he sees her, but he maintains the appearance of being a Handsome Lech while he's actually trying to find out more about Sophie from her sisters.
Ivan Vorpatril from the Vorkosigan Saga may qualify as one, given the way he goes after any good-looking woman. Captain Vorpatril's Alliance suggests he's a Chivalrous Pervert.
Codex Alera: Antillar Maximus, who is determined to have as much fun as possible over the course of his (he suspects, short) life. He constantly snuck out of his room at the Academy, and once he even hit on Gaius Caria, the First Lord's wife. He's also said to have had occasional disagreements with others over the proper treatment of women, making him of a Chivalrous Pervert as well.
Henry Crawford of Mansfield Park. He's not that handsome, but he has a great deal of charisma and wit, plus he's tall, dark and rich. He flirted with his sisters' friends who fell in love with him one after another. He courts Julia and Maria Bertram simultaneously and they both fall for him. When the only single girl present is Fanny Price, he decides he will make a hole in her heart as well. He later genuinely falls in love with her, however, this petite English Rose thinks he's amoral and rejects him, to utter shock of everybody. Her rejection only makes her more charming in Henry's eyes and he continues pursuing her. His love for her shows his better side and improves him a lot, but he cannot resist his ways and later has a love affair with a married woman.
Daniel Cleaver from Bridget Jones' Diary. Handsome, charming, womanizing, cheating.
Garrid from Tales of the Frog Princess. He's hot, but is also a womanizer. Before Li'lcame along, that is.
Thanks to the tutelage of his cousin Lylia, Cullen Moorland of A Brother's Price is shaping up this way. He's entirely fascinated by sex, but because it's important that he remain a virgin until marriage, the best he can do is flirt, which he's become good at. Eldest Whistler finds him harmless and charming.
Allison Chou-Harrington, mother of Honor Harrington, plays at being the female version of this. In truth, she's faithful to her husband, but she enjoys scandalizing the more prudish members of society.
Sergeant "Chopper Jim" Chopin in the Kate Shugak mysteries by Dana Stabenow. He is nicknamed "father of the Park" because of his sexual proclivities (although he is actual very careful to ensure that he has no children). He is eventually transformed into a Lady Killer In Love.
Captain Jack Harkness of Doctor Who and Torchwood is utterly charming and so strikingly handsome that Even the Guys Want Him. The creators describe him as "omnisexual", and this passes into his behaviour - most of the other characters find his flirting charming and quirky, except the Doctor, who regards it as quite an irritation (except when it's done to himself, naturally):
Jack: (to a man) I'm Captain Jack Harkness, and who are you?
The Doctor: Stop it!
Jack: I was just saying 'hello'.
Owen Harper from Torchwood. This is, at times, due to the influence of handy-dandy alien pheromones, but he's rather a ladykiller on his own.
Lord John Marbury of The West Wing. Every female character appears to like him, sometimes even going so far as to profess love (in his absence) yet there is no evidence that he's gotten past flirtation with any of them. Kate Harper seemed to be the first (female) character not to find him charming at all, and Lord John seemed to find this quite jarring.
Lord John Marbury:Abigail! May I fondle your breasts? (said to the First Lady at a White House reception)
NCIS: Tony DiNozzo was this initially but Character Development has gradually guided him away from this kind of behavior starting with season four. It helps that Ziva, a Badass Israeli who can snark right back and turn his come-ons around on him, became his partner in that season.
Hawkeye on Mashwas sleeping around with all the attractive nurses who mostly fell for him, but struck out several times as well.
Barney Stinson, from How I Met Your Mother shags one bimbo after another and keeps scores of his conquests. He devised plenty of tricks how to manipulate women into sleeping with him. He gets a few slaps and drinks in his face. Although he's not without his redeeming qualities, shown especially in later seasons.
Charlie Harper in Two and a Half Men is the guy who would be in the dictionary under "man-whore" if the word was in there. It's made all the weirder by the fact that his (current) career is writing children's songs.
G'Kar from Babylon 5 started out as Handsome Lech. He's had liaisons with multiple human and Centauri (his much hated blood enemy) women. In one of the first scenes we see him, he's trying to convince the resident human telepath Lyta Alexander to sell her genetic material to re-introduce the telepath gene into the Narnish gene pool. Several seasons later, she asks whether the offer is still valid.
Oz. Unit Manager Tim McManus manages to sleep with every female character who works in the prison, but this backfires badly when Psycho Ex-Girlfriend Claire Howell hits him with a false sexual harassment charge after he dumps her. McManus admits that even though he's not guilty of the charge, he is guilty of acting like a jerk towards women.
The title character of Life With Derek strikes out about as often as he scores.
Detective Jimmy McNulty of The Wire is prone to banging random chicks in the most inopportune places possible. He's a Fair Cop and ladies like it, but his ex-wife is disgusted with him.
Lt. Templeton "Faceman" Peck from The A-Team. It helps that he's an awesome Con Man who tends to scam his way into penthouses, so he can make women believe he's rich and powerful.
Alec/X5-494 on Dark Angel, is attractive (he's Jensen Ackles) and flirty but isn't seen to have much success. Asha is hung up on Logan, Mia is manipulating him to help her boyfriend and bring down a mob boss, and it's a matter of fan interpretation whether he's interested in Max that way. One time we see that he has been dating two of his Jam Pony co-workers at the same time, they found out about it and quit.
Sebastian Smythe from Glee is as of the Sectionals episode of season 3 too new a character to know for certain, but he seems to be this, what with hitting on a clearly uncomfortable Blaine right in front of his boyfriend.
Bright Abbott of Everwood. He's a charming Jerk Jock/Lovable Jock and girls at school swoon over him. He even manages to convince several girls to go with him on the prom at the same time. However, it later bites him in the butt when he's almost sued for sexual harassment by a woman from work who felt jilted that he wasn't serious about her. He's also not pleased to realize that women see him as someone who's fun to date, but not a serious guy to settle with. He gets better when he falls for Shrinking Violet Hannah.
Dean Winchester from Supernatural: A very handsome man (his actor was a former model and much has been made of his looks on the show), he flirts with anything in a skirt. The man's first thought upon returning from the dead? He had to re-lose his virginity. Anytime he's shown on a computer or with a magazine, it's invariably open to Busty Asian Beauties.
Possible example: Tucker from Red vs. Blue. We don't know for certain that he's Handsome, but he was once described by his (admittedly ridiculously nice) CO as having "metrosexual good looks". The Lech part can't be in any doubt - he'll try to "charm" his way into the armour of any woman he encounters, no matter how badly she can (and cheerfully will) kick his arse. If there are no women around, he'll take any opportunity to brag about his (potentially fictional) sexual conquests or throw in some innuendo. Bow chicka bow wow!
Drood - John Jasper to the extreme; though an absolute and total creeper (albeit due to being way bipolar), is often played as a charming and handsome man, and there's no doubt that Rosa feels something for him, as disturbed as she is at the same time.
Guido Contini from 9 is a first-class charmer who just can't stay faithful to his long-suffering wife.
Robert is more or less portrayed this way in the musical Company, as he juggles three girlfriends, enjoying a little of each but without showing signs that he really loves any one person (which "Being Alive" suggests is his deep dark desire). He's just good friends with a bunch of married women and their husbands, who envy his hedonistic bachelorhood.
The character of the Trickster from Cirque du Soleil's KOOZA is portrayed like this, wooing every girl he sees with his magnetic charm and gaining fans from the audience.
The Moon Is Blue Defied this with David Slater, a divorced, middle-aged avowed hedonist. He promises not to make passes at Patty, and to her amazement and Don's, he keeps to his word.
Patty: Oh, you're not nearly as depraved as you'd like people to think.
Zelos from Tales of Symphonia, who made it clear that he would hit on anyone remotely attractive, race, age, or tendency to smack him silly be damned. If you have him as your active character, he really will flirt with every single female NPC you talk to (regardless of age). With the correct EX Gem skill equipped, he'll even charm a random item or money out of them (even from eternally depressed half-elves). Later on it's revealed that his personality is mostly a facade to compensate for his very overall lousy life. It's revealed in a skit that not only is his lechery a mask, but his stupidity is as well. He's at least as smart and educated as Genis, the academic mage.
Sean Webely in Super Robot Wars Original Generation, who is tempered by both his age and the fact that he truly is an Officer and a Gentleman. He doesn't leer, grope, or even hit on the many attractive females in the group, but he does make it clear that he definitely appreciates their presence. He is responsible for forcing one character to permanently wear a maid outfit.
Zack in Final Fantasy VII was described as a 'ladies' man' in the original game, but Crisis Core and additional materials reveal him as more of a cheerful, harmless flirt and all-around good guy. Note that the person who describes him as a 'ladies' man' is Aerith, who'd just spent almost five years waiting for him to come back from a mission. Or at least answer one of her 89 letters.
Edgar of Final Fantasy VI... though despite being very attractive, a master inventor and a king, none of the women in the game fall for his playboy act whatsoever. It apparently works at least on one woman seeing as how he finds out about about The Empire betraying them later on in the game. There's a girl in Figaro Castle during the first trip there who says only 'most women are too smart to pay any attention to him'. Emphasis on the the 'most'.
Zidane "oo, soft" Tribal of Final Fantasy IX. The only girl that he doesn't flirt with (or better put, only does as a joke) is Freya. Unlike every other girl he's hit on, she's a giant humanoid rat. She was also in a committed relationship, though her love is currently MIA. She also hasn't given up on finding him, which Zidane is aware of. Zidane stops flirting with other girls as the game progresses and he falls in love.
Jansen Friedh from Lost Odyssey who goes as far as showing up drunk and in the company of three women as you leave on your first mission. His behavior, however, changes drastically when he falls in love with Ming.
Nothing stops Snatcher's Gillian Seed, even the fact that he's technically married. In the original Japanese version he can go so far as to sniff the panties of a fourteen-year-old girl - mercifully, in the American version, the panties were taken out and the girl was aged up.
Jonathan Ingram from Policenauts. Not only does he get a chance to hit on many of the girls he meets along the way (including the teenage daughter of his old partner), the player is even given a choice to fondle the breasts of every female character (including the aforementioned daughter of his partner) in the game.
Yoshitora from Samurai Shodown; he can run away from the middle of a fight if a girl calls his name. He's also the heir to the friggin' Tokugawa shogunate.
Johnny from Guilty Gear is the leader of an all-female pirate crew and makes advances on every woman he sees. This eventually backfires.
Ezio Auditore da Firenze from Assassin's Creed II. By the end of the game, he has either attempted to or successfully slept with every female character that he meets that isn't related to him. The ladies don't seem to mind. By Assassin's Creed: Brotherhood, however, Ezio's habits have changed. In his forties, he's shown flirting with a woman who promises to reward him later and hooks up with Caterina Sforza within the first half-hour of the game... then Uncle Mario is killed, his home villa is conquered, and Caterina is captured and sent to Rome; when Ezio rescues her, she reveals that she only slept with him to secure an alliance between them. Ezio takes it in stride, but he's not shown flirting with any women after that. Though this could also by caused by him growing older and reflecting on his disastrous First Love. Nonetheless in the Da Vinci Disappearance DLC he's not above trying to seduce Lucrezia Borgia to get what he needs. In Assassin's Creed: Revelations, he's still quite the womanizer in his fifties, though his main love interest is Sofia Sartor, with whom he eventually settles down and has a family with in his final years. According to Word of God, while Desmond Miles is presumably a descendent of Ezio and Sofia, Ezio may have fathered many illegitimate children in his lifetime.
Sean Devlin from The Saboteur. One of his escape methods when he sets off alarms is to make-out with random women on the street until the Nazis run right past him. There's even an achievement for using this method of escape 50 times.
Taichi is pretty shameless in his attempts to sexually harass the female cast. He does have some standards, and tries his best not to go too far. He already did cross the line with half of them, which is why they hate him so much. It's a mask to hide some serious issues.
Luka from Bayonetta will never not flirt with a sexy lady. No, it does not matter if he's currently running away from the police. No, it does not matter if they apparently murdered his father. No, it does not even matter if they don't live in the same universe. He lists off the girlfriends he's had at one point: Claire, Sylvia, Trish and... Ammy?
In Always Remember Me, Hugh, one of the love interests, shamelessly flirts with and pursues the main character, and at one point, they jokingly trade cheesy pickup lines.
In BlazBlue, Kagura Mutsuki flits between Handsome Lech and Chivalrous Pervert. His brief introduction in Heart Remix establishes him as a ladies' man when he flirts with Mai Natsume and Estella McKenzie and is described by Taro as a potential sex offender if left unchecked. Heck, his special match intro against Makoto has him parried for trying to cop a feel.
Solid Snake in Metal Gear. He hits on girls half his age! He hits on his support staff! He reads Playboy magazines to restore his psyche gauge! He broods over whether or not it's a good idea to hit on Otacon's stepsister! He seems to have a pretty healthy libido, but he's not quite as successful as his behaviour would suggest. His war experiences have left his ability to open up to other people quite stunted. Meryl was more of a combat buddy than a woman, and even she dumped him.
Makoto Itou from School Days certainly fits here. He's quite good looking, but in most adaptations of the story, he's quite The Casanova with little concern for how his actions may come to affect others, so he has almost nothing to be proud of. Especially in the anime, where he barely atones for his mistakes, unlike in the manga.
SHUFFLE! has Itsuki. He's mostly shown to be turned down, but he still gets girls to give him lunch boxes every lunch.
Sven Bianchi from Questionable Content is known for his ability to (figuratively) charm the pants off practically any girl he encounters. He prefers blondes. Sven recently (after being threatened by Faye) is trying to move past his man-whoring days, but can't even tell when he is being sincere any more. Especially now he's sharing his bed with the same Faye on a regular basis. Late he isn't a whore anymore. Other girls seem "flat" compared to Fay. Poor fellow Fay broke him.
Brad from Gnoph is a very villainous example; at one point, he gropes his imprisoned ex-girlfriend - whom he himself arrested - while telling her that she's going to be executed without trial.
Rainer from MSF High is either a Handsome Lech or a Chivalrous Pervert. Amongst other things, he's used his 360 vision to look up girl's panties, attempted to have one of his friends turned into a cute girl. (By the Friendly Neighborhood HIVE MIND!), and one telepath mentioned his mind 'was like a sewer'. Still, he's a really nice guy who has helped couples get together, at risk, (or LOSS) of his own life!
Vallant from Teh Gladiators, whose backstory involves being kicked out of the door naked after an attempted conquest goes wrong.
Jacob Freeman from Shadownova gets sucked into the plot because he was trying to flirt with the main character at the wrong time. He spends a lot of time teasing the female cast but he's really just a harmless idiot.
Eloya of Seekers is interested in the heroine for one thing - her curves.
Matt, a bisexual underwear model and serial cheater. There was a moment where he reflected on how much of a jerk he is, but it was during a threesome after breaking up with his girlfriend because he'd had sex with his ex-boyfriend (who was an ex because he came home early and caught Matt with the girlfriend.) And no, the threesome didn't involve either ex.
Zii, a rare female version who is generally better than Matt, if only because she tries to avoid getting into relationships that don't let her play around. She still has virtually no sense of consequences.
Dmitri from Spacetrawler. One of the first things he did after finding himself caught up in an epic Space Opera was download an app on his space-smartphone that tells him the anatomical compatibility of any alien species he encounters. Among the aliens he's bedded, he's also something of a Memetic Sex God. Much to his own disappointment, his character development has been shifting towards Chivalrous Pervert.
Sluggy Freelance's Sam constantly hits on any girl he meets, however, he has an awe-inspiringly terrible record at it despite being endued with hypnotism and being far stronger and faster that most of the cast.
In The Gamers Alliance, the blind swordsman Jono keeps flirting with girls and tends to be quite successful with bedding them. However, when he finds a challenge from Vaetris who doesn't fall for him quite so easily, he's intrigued and smitten by her. They eventually grow close until Jono discovers to his horror that Vaetris is in fact one of the four dreaded archdemons who has been deliberately manipulating his feelings for her to achieve her sinister goals.
Lizzie thinks all the swimmers who she met at the Carter's bar are Handsome Lechs. She's not above some classy and lady-like flirting with attractive sport guys, but they are according to her all drunk and behave like utter losers.
George Wickham presented as a sophisticated swimming coach. His flirting is with Lizzie was enchanting and she really liked him. The ever level-headed Lizzie falls for him and when their relationship doesn't go anywhere, she says they were only casual and that there are no hard feelings and thinks well of him. However, his personality has more negative traits than positive ones. She's later absolutely disgusted with him.