Chasing Deadends

"He keeps hanging on to the past and spending all his time hanging out with ex-girlfriends who are unavailable, or women who like him but he doesn’t romantically like."

- SqueakySnapdragon

Baby Talk

"I always wondered why she couldn't get a date because she is gorgeous until I saw her flirting with someone."

"The first night they met, flirted, and swapped numbers. Then, she was immediately clingy, talking in a baby voice to him, and making baby noises."

- robocop_robocop

Body Odor

"I can smell them. Everyone can smell them."

- not-read-gud

"You should find a way to tell them, it might hurt but they'll appreciate it."

- iciclesnbdayclothes

The Nice Guy Mindset

"He really is not as nice of a person as he thinks he is."

- Rusti3dp

"The ones who claim this rarely are."

- SummerOfMayhem

Impossible Standards

"The people they like aren’t real. They are idealized, cartoonish caricatures. Now my friend himself has a lot to offer in my opinion, but he is looking for a person who doesn’t exist. Hard to find something that’s not there."

- Sufficient-Spell9935

"I have a friend who started dating his flatmate after being really into her for a while, and then after a week or two said something like, 'Dating you doesn't feel as good as I thought it would,' TO HER."

"He basically torpedoed his own potential relationship because of his own ideal fantasy, and to be honest, I don't know if he actually realized he'd created an unrealistic standard in his own head."

"He's been single for the last decade, his mental health has only got worse in the time I've known him despite therapy, and I think he's probably so detached from 'appropriate dating behavior' at this point that he could be single for the rest of his life."

- fish993

Questionable Humor

"Brother-in-law, not friend. But he makes the same jokes about poop and farts all the time. Like, constantly."

"Yes, some women like potty humor, but they usually also want it to be funny."

"He is also very negative; finds insult or something wrong with any situation."

- EatYourCheckers

Living in Fantasy Land

"He lies to himself about almost everything. He lives in fantasy land."

"He thinks he's in the gym five days a week, eats great, climbs mountains, goes camping, and makes loads of money."

"In reality, he's at the pub five days a week, over eats like s??t, went on one hike in January, can't hold a job, and lives paycheck to paycheck..."

"If you were to confront him with this reality, it wouldn't even get through to him."

- Fit_Yogurtcloset_291

Mismatched Attraction

"The type of guys she claims she likes isn't what she's actually attracted to."

"She keeps saying how much she loves shy introverted sensitive guys but when she finds one and dates him suddenly, she's like, 'He's not outgoing enough, doesn't speak his mind enough, and is too shy!'"

"I kind of think she has this 'I can fix him' syndrome and doesn't really acknowledge it. Like, she's attracted to the idea of a typical shy guy but thinks once they're in a relationship they'll suddenly be more open and turn into the guy she actually wants. That's not how it works!"

- Disig

Poor Self-Esteem

"She is so lovely. So kind, so generous, and so beautiful. But her crippling lack of self-esteem is so huge, it's visible from space, and her anxiety (and I'm 99% sure her undiagnosed ADHD) means that when she's at all nervous, she talks at 100 miles an hour in several directions at once."

"It's like being handed eight happy Labrador puppies to try and hold in your arms. I so badly want her to be happy and feel fulfilled but even I find it tiring sometimes."

- butwhatsmyname

The Negative Attitude

"I have two of these."

"One is the most talented, smartest, wonderful person I know and I wish I could pull the gremlins out of their brain so they could be happy."

"The other is self-fulfilling proficiency f**king up their life. He's not unlovable, or ugly, or uncared for, but walking through the world expecting rejection at all turns and living in a fog of negativity is what makes him unattractive to be around."

"So-and-so isn't hotter than you, that's not the reason they're getting more friends and lovers, but they are more positive and interested than you, and people are attracted to that company."

- cool_username_iguess

Just Pure Arrogance

"For my husband’s friend, it’s the selfish arrogance. I want what I want, and the subtext was that he never cared about what his girlfriend wanted."

"He would only go places he wanted to go, which never included her friends or family. He wanted to spend all his money on 'collectibles' related to sci-fi movies, DVDs, figurines etc."

"Engagement rings were a waste of money, investing, or buying a house ditto, no compromises were possible, he said NO, and no discussions were entertained."

"His opinion on every topic was the correct one, and he was not interested in your opinion, or listening to extra facts he did not know that might change his mind."

"He was once young and good-looking, and he thought he could find someone else when she walked when he was 32. They had dated for close to a decade. During the relationship, he had started to stack on the weight and losing his hair and he was not able to find a replacement."

"Now he is 49 and hasn’t had a girlfriend since. He still has not bought a house and they cost double what they did when they were dating, and his rent has tripled. He does have a copy of all his favorite movies in every format: VHS, DVD, AND BlueRay, a whole bedroom is dedicated to storing them, if you can get in there. His house is a hoarder's paradise."

"He says the reason no one wants him is because he is fat and bald, and it does not help, but it’s not the major turnoff."

"As for his ex, I don't really know what happened to her. She left all of us behind when they broke up. I did hear she got married, but no updates after that. She is a sweetheart, I wish all the good things for her."

- vicki153

Impossible to Move Forward

"Summarizing two types of my single friends:"

"Super successful, smart, funny, and good-looking. They also tend to go for folks who leave them on read for days. Their insecurities are their worst enemies and I think are the biggest factor of them chasing after partners who don’t want to be partners."

"Other friends don’t know how to commit to anything, including a job. It almost feels like a 'it’ll happen when it happens' type of ideology and so they don’t even try to make things happen? They act like things will happen on their own? So they’ll meet a person and then that’s it. Meet cute dead in the water."

- thunderkitty_

Too Desperate

"Desperation. From laughing way too hard at mediocre jokes to bringing up marriage on the first date, she reeks of it."

"We have all tried talking to her about it to no avail. The sad thing is that if she was just her regular funny, smart, relaxed self, then men would be falling over themselves trying to get her number."

- Julia_Sugarbaker123

A Want List

"Her standards are excessively too high. She brings nothing to a relationship. She's a walking contradiction, all of which is why she is single."

"I think it's great to have standards and high standards but hers is just a checklist of wants."

- Theunpolitical

Height Insecurities

"He’s convinced women won’t like him because he’s short. I keep telling him I know plenty of guys just as short as him in great relationships, I’ve dated guys as short as him in the past. He just refuses to believe it."

- MichaSound

"I dated a guy who was four feet, nine inches, and I'm five feet, four inches. He had such an amazing strong personality that you never noticed his height."

"I did find kissing standing up weird; the motions are so different when it's swapped."

"The relationship ended for other reasons than his height."

- lonelyronin1

Alternatively, Open to Feedback

"I had a friend who finally did just ask. He came up to the girls in our group and just let us have an open conversation. I'm sure it was awkward and uncomfortable for him, but we gently laid out some issues. He cut his hair, got some new clothes, and (the big one) started therapy."

"A couple of years later, guess who's got a wife and a wonderful child?"

- Stars-in-the-night

It's so disheartening to see the people we care about unable to have something that they would find so fulfilling like a long-term relationship.

But it's even worse when the reasons behind it are things they could work on, if we only had the guts to tell them or if they were open to hearing it.