Hollywood Dateless

""Honestly, any guy with a motorcycle that has this much trouble getting a woman to talk to him might just have to give up, but I understand this is Hollywood dramatics.""

- The Agony Booth recap of Ghost Rider

Closely related to Hollywood Homely, and a subtrope of Informed Ability. This trope is a reference to those Sit Com characters who are constantly referred to as being totally inept with their preferred sex and never scoring, when we've seen them with more beautiful people on their arm than most people have ever met, and are sometimes quite attractive themselves. (A 2007 survey indicated that the average American man has seven sexual partners in his entire lifetime. The average American woman? Four.)

As well, in general it seems that if you don't have sex at least once a month (let alone a date) then that constitutes as a pathetic social life.

The big thing to remember is that the solitary nature of only a few dozen episodes a year means we are only seeing a small fraction of the lives the characters lead. Two or three dates over the course of a season can still indicate a lot of empty weekends. Also bear in mind how many times the characters actually "score", as it's entirely possible they got their reputation from getting all these dates but perpetually screwing them up.

The flip side of the Cool Loser and Attractiveness Isolation. Often results from Negative Continuity. Contrast Urban Legend Love Life. Can be used quizzically in combination with Everybody Has Lots of Sex, Failure Is the Only Option, Moment Killer, Derailing Love Interests and This Loser Is You.

Comic Books

 * Peter Parker (a.k.a. Spider-Man). He was married to one of the most beautiful women in the Marvel Universe (before Executive Meddling kicked in). And before MJ, he dated Gwen Stacy and the Black Cat. This despite him being a poor nebbish nerd. His friend the Human Torch even called him on it, as did the Chameleon while impersonating him ("Does Parker know anyone who isn't a stunningly beautiful woman?").
 * Dilbert.
 * In some strips, this goes Serial Escalation . Women try so hard to deny his requests without seeming callous, using all sorts of ridiculous excuses, from deliberately misunderstanding him, to saying that it would be against her religion (apparently there's an entire religion devoted to avoiding Dilbert), to claiming to be clinically dead and the reason she's still walking and talking is just the random spasms of her dying brain.

Film

 * Dante from Clerks and Clerks II. The same Cool Loser having to choose between two different, noticeably attractive women in the first movie and then a second pair of attractive women in the sequel. Notice Lampshade Hanging by both Randal and Kevin Smith himself in the credits.
 * Warren Beatty's character in Ishtar. Yes, that Warren Beatty. The character claims to have never dated anyone but his ex-wife in his life and that women "just don't like me."
 * Gary is the eponymous character of The Last American Virgin.
 * Summer Glau's small role in the film Sleepover. Most people would agree Summer's nicer looking than most of the main female actresses.
 * Jennifer Lopez' titular character in The Wedding Planner, who is depicted as so lonely that she's willing to settle for marrying a man she doesn't love to save herself from spinsterhood. This is Jennifer Lopez we're talking about. Hell, her fiance could count too. Sure, he's no Matthew Mc Conaughey, but he's hardly so ugly that he would need to settle for a woman who doesn't love him just so he won't be alone.
 * Melvin Udall (Jack Nicholson) in As Good as It Gets is an incel due to his misanthropy.
 * Never Been Kissed, where the protagonist, who has never been kissed, is played by... Drew Barrymore.

Literature

 * Harry Dresden. The man's friends, co-workers, and magical spirit servants mock his lackluster love life. His love life actually isn't all that great - the books, 11 so far, each take place about a year or so apart, so he's had two girlfriends in about 11 years - but it's not all that horrible. Over the course of the series he has been in two committed relationships so far with very attractive women, plus one paper-thin Will They or Won't They?, one at least somewhat attractive lover in his backstory, and probably dozens of women who have thrown themselves at him only for him to turn them down. His love life isn't that great only because Harry has a Dark and Troubled Past and a tendency to place Honor Before Reason, not because he's really all that ugly or socially inept. In the books he's tall, dark, mysterious, probably relatively good-looking when he bothers to clean himself up, and has a sharp wit. In the TV series he was played by this guy. There's no way he couldn't get a date if he actually wanted to.
 * Harry's situation is made somewhat worse when you realize that neither relationship lasted very long. And he appears to have had sex once in the ~7 years between Grave Peril and Small Favor. His problem may be just that he doesn't get out enough. Seriously, does the man have any friends he didn't meet through his working life?
 * A large factor in this is that he's, by his own admission, a loner, very set in his ways, and a bit of a geek. He doesn't get out much, and when he does go out for a good time, it's usually to a bar where everyone there is either distantly respectful or outright afraid of him.
 * Harry ALSO has rather severe abandonment issues. He needs to know the relations will last. Without that, he won't dare to get into it.

Live Action TV

 * Oscar Madison on The Odd Couple. It was the running gag for an entire episode where Oscar could not find someone to take to a Broadway show and the boys wind up getting arrested for ticket scalping. In another episode, Oscar uses a computer dating service. He embellishes his personal info and he is matched with Felix's ex-wife, Gloria (both used pseudonyms on their applications).
 * John Dorian on Scrubs. Yes, he is a doctor, but DAMN!
 * Everyone in Chuck Bartowski's life regularly acts like him getting a date of any kind, let alone one with a good-looking woman, is a minor miracle. This continues approximately through the end of the second season, despite the fact that in that space of time he dates two beautiful women and has a third one in love with him. For the most part the third season drops the facade, though.
 * Jeff in Coupling.
 * Chandler Bing from Friends, despite being good-looking and incredibly witty, is constantly knocked by himself and others for having very little in the way of a love life. Gunther and Ross also count if you really get down to it.
 * One episode, a while after he became, involved him not even being able to TALK to a women because she was beautiful, only being able to bashfully mutter a few whispers, and the characters acting like this had always been the case with him. Over the course of the past six or so seasons, Chandler had been shown successfully making some of the boldest and most hilariously charming pick-ups anywhere on television, to complete, gorgeous strangers.
 * There's also the matter of Monica frequently vocalizing her aggravation earlier in the series over not being able to find a boyfriend. She looked like this at the time.
 * Another time, Rachel mentions that Monica "stumbles down the hall and sleeps with the first guy she finds." It may be that she's having trouble finding a committed relationship.
 * Of course, that was just in reference to the other holder of this Trope, Chandler.
 * Commandant Klink from Hogan's Heroes. The irony of it is that the women he has the most success with are actually enemy agents seeking to use him in some plot. Otherwise they would run a mile.
 * Charlie in Its Always Sunny in Philadelphia.
 * Charlie being dateless is actually quite justified, he's borderline retarded, lives in a dilapidated apartment and is regularly called out on having terrible hygiene. The only dates we ever see him on are ones the guys set him up on. He proceeds to torpedo these spectacularly. Dee on the other hand regularly complains about having trouble finding men yet in the "Dee Gives Birth" she's shown to have several regular sexual partners, two of which are actually in excellent shape and declared by the guys to be "legitimate lays".
 * Cabbage Head on The Kids In The Hall.
 * In Sabrina the Teenage Witch there is Miles who has continuously been referred to be beyond all hope when it came to make a positive impression on the other sex (or people in general) despite looking like this. Most run away before he gets a chance to introduce himself.
 * Perhaps the most notable example is George Costanza, whose role in Seinfeld is a slow-witted, self-centered, ugly failure who repulses women and can't get them to go out with him... except for, oh, the forty or fifty gorgeous women he dated over the course of the show. He even got a model whom he suspected was bulimic. He winds up getting engaged to the attractive daughter of a rich, Upper East Side, WASPy, old money couple- Susan Ross. Even if they were evenly-matched looks-wise, it's completely far-fetched status, class and money-wise.
 * The worst episode for this is "The Strongbox" when George wants to break-up with a gorgeous woman because she talks to her food but she refuses to end the relationship. Finally, he sets it up so she'll catch him on a date with another gorgeous woman (who we learn had pursued George in the past but he had rejected for being "too tan") in the hopes that both women will dump him. However, they both take his infidelity in stride and announce that neither are ending their respective relationships with him and the episode ends with George having the "problem" of two hotties refusing to let him go no matter what.
 * Neither of whom he wants a relationship with and neither of whom will respect or accept that. It is a problem.
 * George was also notoriously picky. When Elaine was setting him up on a blind date, he asked multiple shallow questions about her physical attractiveness. Another episode had him breaking up with a woman who wore a wig despite wearing a toupe himself. All of these women were attractive.
 * Susan was Hollywood Homely at worst, this troper considered her too cute for George.
 * Then there are episodes that seem to go the other way. In one, George claims that all he has to do to get a woman to want to date him is to see her on three separate occasions. He compares it to an advertising jingle: annoying as hell the first time, but by the third time it's stuck in your head.
 * Dorothy Zbornak on The Golden Girls.
 * Bud Bundy, Married With Children.
 * Worse than the George Costanza example, because Bud actually touches himself every single night out of his loneliness, always whines about being dateless, rejects girls at a higher standard than him, and still he scores repeatedly. Fail.
 * But unlike the George case, there is certainly a high ratio of on-screen rejections to on-screen incidents when he does score. And when he does score with an attractive female, he quite obviously feels that he's "getting lucky" rather than "this is something that happens to him all the time." And George's women are (short-term) girlfriends, while with Bud there's usually a sense that he would have just as much trouble getting a second date as he does getting a first. As for the whining, Bud's real problem is that, when Kelly wants to insult him, she uses his involuntary celibacy as her go-to first talking point.
 * Xander Harris in Buffy the Vampire Slayer who spent most of the series in a long-term committed relationships with either Cordelia (early on) or Anya (Season 4 to the end). Also, he has a one night stand with Faith and Willow wanted him.
 * In the first couple of seasons it's a running joke that he does get dates - but they're all with demons disguised as women.
 * As of the Season 8 continuation-of-the-show comic series, Buffy confesses her love for Xander. He turns her down, since he's now in a relationship with Buffy's sister as he believes Buffy has just finally gotten to the settle-for-the-best-friend option (after "trying girls", mind you, so he might be right.) Earlier in the comic he was dating a Slayer named Renee, who.
 * Despite the title of her show, Ugly Betty manages to have plenty of cute guys pining after her. No, she's not really ugly, but she dresses like a clown on acid.
 * Brian Hackett of Wings dated many beautiful women over the course of the show's run. For most of the show, he was The Casanova, but for some reason, the last couple of seasons seemed to have a lot of jokes about how he was having trouble scoring dates.
 * Lampshaded on Wizards of Waverly Place when Hollywood Nerd Justin asks his brother "Why does everyone think I don't date; remember the centaur, the werewolf and the Goth Girl?" The "goth girl" was in fact his established girlfriend for a several-episode arc.
 * This is actually creeping into Unwanted Harem territory.
 * This is largely due to the utter inability of the show's writers to convincingly ship Justin with anyone other than Alex. And the one time they DID manage it, they turned right around and put her on a bus to Hell within five episodes.
 * Liz Lemon on Thirty Rock. She's dated Jon Hamm, for goodness' sake.
 * The show does make it out to seem more like she doesn't have a problem finding men to date, but rather that everyone she does date turns out to be completely insane in the end so she's forced to end all her relationships.
 * Also, Liz has plenty of her own problems to sort out so her trust issues/childhood trauma involving posters/etc. might have some effect.
 * Amanda Marcotte, of the feminist blog Pandagon, argues that Liz herself sabotages a lot of potential relationships because she's actually happy being single.
 * Alex Reiger was Flanderized into this at the beginning of Taxi's final season. To be fair, though, the writers got back on the ball pretty quickly and Alex went back to being his normal self.
 * Goober Pyle on The Andy Griffith Show is shy and awkward with women.
 * Malcolm and Reese on Malcolm in The Middle
 * Frasier, who despite having a seemingly endless supply of beautiful and sophisticated women going out with him, is often said to be unable to get a date.
 * Frasier's problem is generally that he usually has trouble holding onto a girlfriend, usually due to some contrived circumstance he happens to fall into in her presence.
 * Carlton in The Fresh Prince of Bel Air.
 * Ted Mosbey's love life in How I Met Your Mother is generally unsatisfactory to him (to be fair, he is looking for true love, so it'll take a lot to satisfy him), and is often teased by his friends as being awkward and shy around women. Still he has several hot women per season, (minus season II when he's in a committed relationship with Robin).
 * Brooke Shields (!) in Suddenly Susan.
 * "Lowered Expectations" on Mad TV their video library allows you to choose from thousands of chronically rejected singles just as hard up and pathetic as you. Their motto: "Lowered Expectations, when you've been blown off by the rest, settle for what you can get!"
 * Rachel Berry on Glee. It sort of makes sense at first since she's established as very obnoxious and the two guys she is romantically involved with in the first half of the season are in a Love Triangle over a more popular girl. But by the second half she's in the center of her own Betty and Veronica and throughout the entire series she's had a huge Stalker With a Crush in the form of a nerd who even at one point blackmails her for her panties.
 * Freddie on I Carly averts this, in both ways. He is never considered to be completely inept, but neither is he constantly dating insanely hot girls. 1 date was a Femme Fatale who was using him to break up their webshow, a second was with a twin he only asked out to prove that it was a trick being played by the original twin, he went to a dance with a wizard that ended poorly, and finally a date with a girl he wasn't interested in due to being forced into a triple date. The only time he's been with a girl he really likes, it's Carly, but he had been recently hit by a truck and was stuck in bed and then hobbling around on crutches. He also ended their brief relationship because he was worried Carly only liked him because he saved her from the truck.
 * Leonard from The Big Bang Theory, though a lot of this comes from his experience before he became friends with the pretty Girl Next Door who gave him a lot more confidence. It was said the only girl of real significance in his life (not counting minor flings) before Penny came around was Joyce Kim, later revealed to have been a North Korean spy pushing him for government secrets. The few times he is seen in a social situation he is shown to be shy and awkward, but starting in the second season he briefly dated Leslie Winkle and Stephanie Barrett, dated Penny for the majority of the third season and had a long term relationship with Priya Koothrapali that crossed the fourth and fifth seasons. In between those girls, though, it's clear that he doesn't have that great of a social life.
 * Timothy McGee from NCIS, who, while being a geek, manages to get quite a few dates, and still is told that he needs to get out more.
 * Alan on Two and A Half Men is often depicted as a pathetic loser yet he's dated a number of attractive women and was even married to a couple of them.
 * Girl watchers Tom Hanks and Jon Lovitz on Saturday Night Live.
 * Also from Saturday Night Live, Not Gettin' Any.
 * Christine of The New Adventures of Old Christine is perpetually lonely and treated like a loser, except that she's dated the likes of Tim De Kay, Eric Mc Cormack and freakin' BLAIR UNDERWOOD. SHUT IT DOWN.
 * Dobie Gillis on The Many Loves of Dobie Gillis, pursues beautiful and unattainable girls when he should be going for Zelda Gilroy.
 * Skippy Handelman on Family Ties
 * Cliff Clavin during the first 6 seasons of Cheers

Stand Up Comedy

 * Richard Jeni said that every porn video should be titled Stuff That Never Happens to You and that they star women you'll never meet.

Webcomics

 * Davan Macintire, main character of Something Positive. Despite numerous characters, himself included, referring to him as ugly and a loser, a fair number of women have expressed interest him and he's had sex with more than a few of them. On the flip side, most of his relationships, potential and otherwise, tend to end badly.
 * Marten of Questionable Content. Something of a subversion in that he only acts this way because he's often oblivious of people's attraction to him.
 * Torg from Sluggy Freelance is, in Bun-Bun's words, a "nerd boy" who's supposed to be relatively unlucky with the ladies. Except, y'know, for Valerie, Angela, Oasis, Alt-Zoe, and (eventually) Prime-Zoe all falling for him. Justified since at least two (possibly three) of those women were just using Torg as a stand-in for previous Love Interests who had died, and another is only in love with him because she's been Brainwashed to do so.
 * Also tends to suffer from the Cartwright Curse.

Western Animation

 * To some extent, Fry, from Futurama. To date, Fry's been with: Amy Wong, Chief of Police Colleen, former girlfriend Michelle, bureaucrat Morgan Proctor, his own grandmother and, of course, Leela, who he's now in a relationship with.
 * Also something of a Flanderized trait. Earlier in the series, Fry dates Amy and goes home with a woman from the 21st century after meeting her at a bar.
 * Don't forget the radiator woman from the radiator planet.
 * And all those Amazonian women. Although admittedly he did end up with a slightly broken pelvis for his troubles.
 * There was also the hot mermaid from the lost city of Atlanta.
 * Kim Possible has Ron Stoppable who's overly concerned with social rankings and considered a loser by his school peers. Yet he seems insanely popular among girls - notably Yori and Kim (the latter of whom he later does date), along with Zita, and a crush by another cheerleader. Not to mention a handful of episodes where he gets involved with Bonnie. Kim herself dates little, despite being a knockout, which she attributes to her crime-fighting lifestyle and type-A drive.
 * Kim: "I'm weirding guys out! They see me on TV, round housing some goon out a window... It's a vivid image."
 * Moe Syzlak, Selma Bouvier, Comic Book Guy, Milhouse van Houten, and Principal Seymour Skinner on The Simpsons.
 * Moe got 600 no's in 1.8 seconds. All the others except Skinner haven't had much better luck. Edna Crabapple used to be portrayed as unable to get a date, but now she's promiscuous.
 * Meg Griffin on Family Guy. She's very unpopular, yet manages to hook up with/date at least: Doug (Prick Up Your Ears), the nudist neighbor she liked, Mayor Adam West, Kevin Swanson, Michael, a medical student, Anthony (Go, Stewie, Go) as well as being pursued by Neil Goldman and losing her virginity on live national television to Jimmy Fallon during the opening of Saturday Night Live.
 * And when a cute, popular lesbian thinks she has a chance with Meg, she's so excited she immediately strips.
 * To be fair, Meg didn't become super unpopular within the show's universe until later on in the series. Most of her dates were prior to her uber-Butt Monkey status.
 * Reverend Rod Putty on Moral Orel.
 * In fact, his daughter Stephanie's conception was when her mother, Gladys Foamwire impregnated herself by stealing Reverend Putty's used tissues.