OP credits go to Adept

This trope is defined as someone who is treated as (or claims to be) romantically inept despite having numerous love interests. A discussion about a misleading page quote shows that several people mistake this trope as something else: that a person is actually unable to land a date, despite being attractive enough to attract plenty, and I did a wick check to see how prevalent this misconception is.

The results that shows that, while the examples that use the latter definition is far fewer than I expected (3/50), there's not many correct examples either (19/50). A lot are ZCE (12/50), many unclear (7/50), and there are plenty of examples that use the trope as a shorthand for just "dateless" (5/50).

Proposed Solution: The page quote discussion mentions how the definition doesn't fit the naming pattern this site typically use. This trope is more of an Informed Attribute ("character described as [insert X trait here] doesn't actually demonstrate trait") than a Hollywood-style trope ("fiction has unrealistic standards for beauty/success/etc."). Renaming might be a good start.

1. Midori Days: In the manga, Seiji has far more options for a lover than just his right hand.
2. The Nostalgia Critic: The Critic: Tropes F-M: Reboot only. He's so sex-starved that he uses Rogue figurines as wank tools, but he has people feeling him up all over the place.
3. Dilbert: He actually does get out on a date now and then, even post-Liz. But he's still portrayed as useless with women.
4. Bored to Death: He tends to complain about being lonely, but he encounters a new Girl of the Week in almost every episode.
5. Frasier: People poke jabs at him not being able to get a girl and he spends supposedly months dateless, but he's getting dates left and right in-show. It's played with in that he gets dates all the time, but 90% of them never go past the first one.
   Frasier: I'm a one-woman man. If that.
6. Flight of the Conchords: The two often mention their sordid love lives, despite dating a number of women throughout the show's run.
7. The Golden Girls: Dorothy. In fact, she's probably had more love interests than Rose or Sophia.
8. The Singles Index: Despite having dated people in the past, this character is treated as though they can never have a relationship.
9. Married... with Children: The show plays Bud up to be a gross, repugnant troll of a guy... but he's gotten laid a fair amount, by a fair amount of women, but most of that is swiftly ignored.
10. The League: Despite his constant complaining about his romantic life, he's had plenty of girlfriends. His standards are just ridiculous.
11. Schitt's Creek: David's family sees him as a complete failure at romance, despite his having an endless series of stories about failed relationships with famous and non-famous people of both genders. When he moves to the town, he attracts Stevie and Jake before meeting Patrick.
12. Three's Company: A mild example. It's strange when Janet complains about not having a date for the evening. She dates frequently but doesn't have a steady boyfriend through most of the series.
13. Fuller House: For someone who complains about not having a boyfriend, she has a lot of boyfriends. Averted once she starts dating Kimmy Gibbler's brother Jimmy.
14. Hollywood Dateless: Lots of Love Interests, complains about being dateless.
15. The Dresden Files – Harry Dresden: Despite the fact that he sometimes laments that he doesn't have much of a love life, Harry is more unwilling to date the women in his life rather than unable, due to his personal hangups and issues.
16. Spider-Man: Peter Parker: He was married to one of the most beautiful women in the Marvel Universe. And before MJ, he had Betty Brant and Liz Allan fight over him and dated Gwen Stacy and the Black Cat. Even his least overtly attractive love interest, Debra Whitman, looked like a Hot Librarian. This despite him being described as a poor nebbish nerd (though Depending on the Artist not really looking like one). His friend the Human Torch even called him on it, as did the Chameleon while impersonating him.
    Chameleon: Does Parker know anyone who isn't a stunningly beautiful woman?
17. New Girl: Main Characters: He has no game, no confidence, no luck with girls, and is mocked for it. Yet he manages to be romantically involved with six women over the course of the show, along with several other dates, and even gets an Unwanted Harem in a later episode.
18. Seinfeld: Is bald, a bit overweight, often unemployed, and his personality flaws are too long to list. The show draws heavy attention to what a loser he is, yet he had sex with 43 (very attractive) women over the course of the show.
19. King Of The Hill S 8 E 22 Talking Shop: Bobby is supposedly hopeless with girls at the start of the episode, despite the fact that he dated Connie and he's had numerous one-off love interests over the years.

1. The Mask: Stanley Ipkiss, as lampshaded by Cinemasins: “I love how handsome Jim Carrey in a nice suit with a good job is somehow a loser with women”.
2. Parenthood: A female example with Sarah; early in the season it is a joke between the women that she hasn't had a date in years, despite being attractive. Possibly justified in that she has two teenagers, and all men are terrified of women who already have kids. Totally not justified in that later on, two very different men who know she has children fall for her very quickly.
3. Love Hard: Discussed, while Josh may not be traditionally handsome he isn't a bad looking guy, but he had only three matches on the dating app. Natalie asks to see his original profile she picks apart his poor choice of pictures (between holding rope as a rock climber, holding a wrench doing bathroom repair and his interest in candles she says he comes across as a Clue character). She encourages him to be more natural in his photos and he would be more successful.

1. Nigahiga: Ryan hasn't had an official relationship since his ex Tarynn from some of his first videos. He admits it's due to him being really bad at dating people.
2. Pretty Little Liars: Views herself as this after divorcing Byron. This is why Hanna and Aria later enlist her on a dating site.
3. Parallel Porn Titles: Pothole to a dialogue of someone claiming to be lonely.
4. My Brother, My Brother and Me: In early episodes, he would be singled out as the brother who wasn't dating someone, with listeners even getting in on it in questions about romance by specifying that Griffin was not allowed to answer. Subverted now that he has married his wife, Rachel.
5. Poor Man's Porn: Bob is lonely and Hollywood Dateless and receives a lingerie catalogue in the mail, and the girl on the cover is a real turn-on for him.

1. How I Met Your Mother: Main Characters: Given that he's a handsome, charming and successful architect who's also a idealistic and optimistic romantic at heart, it's not that he has a hard time chatting up girls or dating in general. It's more so that he is hoping each new date will result in "The One" and tends to get hurt badly when it falls apart. Character doesn't seem to be treated as "dateless".
2. Double Homework: MC acts like a dating newbie on his first date with Lauren (his first since his three-months-long, self-imposed isolation), and speculates bitterly that Rachel must have had several sexual partners in the months since his breakup with her. Justified in that MC is fighting PTSD, and had no social interaction save with Johanna during his isolation period. Character is bitter that their date is more experienced in romance, but doesn't seem to be treated by the narrative to be a dateless loser.
3. The IT Crowd: Andre, though possibly justified, as being a wealthy, successful plastic surgeon probably helps him get dates. He just has trouble hanging on to women. Doesn't seem to be treated as dateless by the narrative.

1. Futurama: Philip J. Fry: In a sense, before taking many Relationship Upgrades with Leela in later seasons. Before all that, he often complained about why no woman would date him. But, he's clearly not as hopeless as he claims, having successfully picked up and slept with plenty of women over the show's run (still, they all admit he's... "meh" in bed). Still, none of them are repulsed by him. Probably correct, but the entry is arguing with itself
2. Ménage à 3: : Gary's shift from virginal and genuinely dateless, through socially clumsy and still virginal but attracting the attentions of several attractive women and going on dates with some of them, to fully sexually active (if still socially inept), is so rapid that he gives the impression of fitting this trope.
3. Friends: The core cast also has subversive powers that very subtly warp reality in their favor...
4. The Masquerade Will Kill Your Dating Life: Mentioned in the trope description, that the masquerade may cause a character to be Hollywood Dateless.
5. Love Actually: Hugh Grant is the first single and unmarried British Prime Minister since Edward Heath.
6. Confessions of Georgia Nicolson: Played straight in the first two books, then it kinda becomes the parody of this trope, with Georgia still complaining about her love life, despite having plenty of boys and love interests. Technically correct, but defined as parodied for some reason, which implies that the "played straight" part may be using the incorrect definition.
7. Brooklyn Nine-Nine: Main Characters: She wasn't actually shown having much trouble getting dates, going on a fair number (before she became the Official Couple with Peralta). Nonetheless, her being a straitlaced and pedantic goody-two-shoes led to jokes from her colleagues that paint her as totally inexperienced in such departments. Other characters treat her as romantically inept, but the narrative itself doesn't seem to.

1. Never Mind the Buzzcocks: Pothole to a character's name
2. Archer Season Seven: Pothole to a character's name
3. Step by Step: J.T. until he started dating Sam.
4. What Does She See in Him?: Pothole to a character's name
5. Popular Mechanics for Lovers: Tim and Arnold. Justified by their feelings for Phoebe.
6. Basement-Dweller: There's a 32-year-old (Hollywood Dateless and unemployed) man who's having trouble cooking for himself.
7. Bat Girl: She says that she has trouble keeping a boyfriend.
8. Fatal Fury - Terry Bogard: Pothole to a character's name
9. Kev Jumba: Played with and parodied.
10. Better than Sex: "They're like sex, except I'm having them!"
11. TV Shows — #-F: Pothole to a character's name
12. The Mentalist: To the extend that she goes to Erica's matchmaking system.

1. Informed Loner