"So no one told you life was gonna be this way. Your job's a joke, you're broke. Your love life's D.O.A". Of course, if you had a friend like Chandler Bing he would certainly point that all out. Indeed, he's sarcastic and witty. In fact, he's the best boyfriend ever. As Chandler would say, "Could I be more wrong?"

It's safe to say that Friends wouldn't be the same without him. He's a good friend, roommate, and neighbor. He always tries his best to be a good friend but isn't always a good boyfriend. As a matter of fact, he's pretty bad a dating at first. At one point it seems like he'll be alone forever. Well, he'd always have Joey. He's not perfect and has many flaws. To be fair, he does end up in a few serious relationships. In fact, he dates Monica and later marries her. Turns out she can put up with all the non-stop jokes.

On the other hand, he's been difficult at times. He can be immature and needy. He lacks confidence but does well on the dating scene. Of course, there have been times when he's romantic and charming. He does know how to sweep a woman off her feet. He also knows how to screw it up and watch it blow up in his face. It's time to take a closer looks at Chandler and his dating history. Here's Friends: 25 Things That Don't Make Sense About Chandler's Relationships.

25 Chandler Can Find The Smallest Detail Wrong With A Date

Chandler has many great talents. He's funny, creative and can find the smallest detail wrong in a person. In fact, he's superficial and very into looks. He ended many relationships for petty reasons. Indeed, he broke up with women for gaining weight. In fact, he even mocked a teen Monica for being overweight. He also finds the need to play games. For instance, he doesn't call the next day because he doesn't want to seem needy. Then he waits by the phone for the girl to call him.

24 He Doesn't Fire Nina And Dates Her Instead

At first, Chandler hates his job and hopes to find his passion. Of course, he doesn't quit for several seasons to try advertising. Instead, he stays in a job he hates and nobody can remember. At the same time, he often abused his position of authority. For example, he attempted to fire an employee that wasn't good at her job. In fact, he was about to fire her until he saw her. He instantly liked Nina and didn't care that she's a subpar worker. Instead, he promotes her and starts dating her. Clearly, this is a bad idea but he does it anyway.

23 Girls Reject Him All The Time But He Still Tries

Chandler is good at so many things. However, talking to women isn't one of them He often claims that he's too afraid to approach women. That's because they always turn him down. Regardless, he still tries to talk to women in public. In fact, for a guy that's not good at it, he's often successful. Women turn him down all the time but he still tries. To be honest, that's a great attitude to have. No matter how many times he hears 'no,' he doesn't give up.

22 He's A Different Person Around His Boss

Clearly, this isn't about Chandler's dating history. His has a unique relationship with his boss, Doug. He's often seeking approval but doesn't want too much. In addition, he acts like a completely different person around his boss. For instance, he often laughs at his boss' lame jokes that don't always make sense. In fact, Monica's not impressed with how he acts. She doesn't like work Chandler. He wants his boss to like him so much that he acts like another person. Of course, Monica agrees with him in the end.

21 Chandler & Phoebe

Chandler and Phoebe are good friends but have had their moments. In fact, Chandler kissed her once. In addition, Phoebe flirts with Chandler to force him to come clean about dating Monica. That's the closest they ever got to being a couple. However, Phoebe makes it pretty clear that she doesn't find him attractive. She's into both Ross and Joey but Chandler's not her type of guy. As a matter of fact, she has no problem letting him know that. She finds him attractive in an unattractive kind of way.

20 Monica's Parents Don't Like Him

It's no surprise that Chandler's not great at making a first impression. This even comes up when he's preparing for a job interview. Chandler and Ross have been friends since college. He did not impress the Gellers the first time he met them. In fact, they didn't like Chandler for years. They thought he was a bad influence on Ross. Turns out that Ross is the bad influence. Regardless, Monica's parents didn't think he would propose and often mock him. It's always nice to get along with the in-laws.

19 He Didn't Invite His Father To His Wedding

Chandler and his parents have a tough time getting along. His parents told him they were separating on Thanksgiving, which is why he hates it. His father then ran off to Las Vegas to become a performer. Chandler had a tough time accepting his dad and didn't speak to him for years. In fact, he would avoid seeing his father anytime he came to New York. Chandler didn't invite his father to his and Monica's wedding either. Chandler just wanted to avoid the situation. In the end, he invites his father to the wedding. However, his father pretty much disappears after that. Of course, the jokes about his father continue.

18 Ross And Chandler's Dating Pact

In college, Chandler and Ross weren't the coolest guys on campus. In fact, they were two huge dorks. Of course, they didn't know that. They often talked about approaching girls but usually just ran away. Regardless, college girls were turning them down all the time. Of course, there were a few girls they manage to date. To avoid fighting over the same girl they agree to a dating pact. Neither of them will ever go after the same girl. This makes little sense considering they weren't going on a lot of dates. In addition, they both broke the pact.

17 Chandler And The Model

Chandler ends up trapped in an ATM vestibule during a blackout. The blackout hits the entire city and there's no way out. Luckily, model Jill Goodacre's trapped with him. Of course, this is every guy's dream but Chandler's slow to move. Eventually, they start talking and she even saves his life when he chokes on some gum. She ends up having a good time with him during the blackout. She even gives a kiss on the cheek. However, he doesn't even try to get her number. He doesn't have to date her and could just be her friend. He finally gets close to dating a model and messes it up.

16 The Popular Girl Likes Chandler

Chandler has many flaws and is far from perfect. The pretty popular girls have never liked him. As a matter of fact, they usually point and laugh at him. When he gets older he's much better at it. However, in his college days, he was a big dork. The popular girls didn't even know he existed. That's why make it makes little sense for the popular Missy Goldberg to give Chandler the time of day. It seems odd the popular girl would be into him. To be fair, she forces him to keep it a secret and not tell anyone.

15 Chandler's Camp Girlfriend

Even as a kid, Chandler would break a girls heart because of her looks. He admits he hasn't done a lot of dating and only had few girlfriends. At one point, he had a summer camp girlfriend Julie. They dated for a few summers but he suddenly broke up with her. He ends things with her because she gains weight one year. It seems odd to just dump someone because of their weight. On the other hand, he was a kid so it makes a bit of sense. Of course, he's still like this for most of his adult life. In fact, he often made insensitive jokes about Monica's weight as well. Years later, Julie approaches Monica and warns her not to marry Chandler.

14 Monica's Only Slightly Mad That He Takes Out Dana Keystone

At one point, Joey asks Chandler to help him land a movie role. Turns out that a woman Chandler dated in college is the casting director. However, Chandler's already with Monica by this point. Of course, he's a good friend so he takes out Dana Keystone. He doesn't consider it a date but Dana thinks he still likes her. He lets her think that to help Joey out. It does seem a bit odd that Monica's only slightly upset. In addition, Joey forgets to go to the audition after everything Chandler did.

13 Tricking Jade

Chandler is a good friend and a good husband to Monica. On the other hand, he has done some pretty questionable things. For instance, he once tricked a woman named Jade into a date. She called his number looking for Bob. He pretends to be Bob and promises to meet her. Of course, he's not Bob. He goes to Central Perk and assumes the most beautiful one is Jade. Chandler then approaches her pretending to care that Bob didn't show up. He actually pulls off his master plan. It's a bit strange that he's okay with tricking Jade into a date. In fact, he's quite proud of himself until it backfires.

12 Chandler Dates A Girl He Met At The Sleep Clinic

As noted, Chandler claims he's too afraid to just approach a random woman. Regardless, he does that many times in the show. In fact, he meets Majorie at a sleep clinic. He takes Joey because his snoring is driving Chandler crazy. He doesn't consider the fact that she's there as well. Clearly, she's there for a reason. One night, she starts screaming in her sleep. Not only does she wake Chandler up but she also scares him. She never appears again, which implies he breaks up with her.

11 He Dates Joanna And Puts Rachel's Job At Risk

Chandler breaks up with a different woman each season. He finds all kinds of reasons to end it. However, turns out he's not good at ending it either. In fact, he often lets the woman believe he's going to call her. For example, he once went on a date with Rachel's boss Joanna. He doesn't like her but doesn't make that clear to her. He puts Rachel in an awkward situation with her job at risk. Eventually, he's honest with Joanna. Regardless, he runs into her on the street and dates her again. It seems unfair to put his friend in that position.

10 Ginger's Leg

Chandler admits to having a tough time accepting a person's flaws. To be fair, he clearly works on this and changes. However, early on he could find the smallest reason to break up with someone. For instance, he had a tough time accepting Ginger's prosthetic leg. Eventually, he learns to accept it but she ends things because of his flaws. Joey also dated Ginger and accidentally threw her leg in a fire. It's odd that they could date the same girl without any problems. In addition, her leg seems like an odd reason to not like her.

9 Chandler & Joey

Chandler and Joey are the best of friends. They share everything. In fact, they even dated the same women. For the most part, this doesn't cause any problems between them. Well, there was the time Chandler stole Joey's girlfriend. Oddly, they made up quickly. Joey often went on dates and would have Chandler do the breaking up the next morning. It's a bit odd that Chandler would do this for his friend. Chandler's a good friend but this is above and beyond.

8 Susie Moss Gets Revenge

Chandler has been making jokes at the expense of other people his whole life. In fact, he's one of those guys that teases a girl he has a crush on. From time to time, those people get their revenge. As a kid, Chandler once embarrassed Susie Moss (Julia Roberts) in front of the whole school. Susie never forgets this and plots her revenge. As adults, they meet again and she tricks Chandler. She steals all of his clothes and leaves him stranded in the bathroom. It's a bit odd that she would hold the grudge against an adult Chandler.

7 Chandler Has A Complicated Relationship With His Mother

As noted, Chandler has a complicated relationship with his parents. Their divorce had a huge impact on him. In fact, he admits to using humor as a defensive mechanism because of their divorce. However, he knows way too many intimate details about his mother. Mainly because she tells everyone. In addition, Ross once kissed his mother. Chandler does get over it but nobody wants their friend and mom to get that close. He does remain close with his mom for many years. On the other hand, he drifts away from his father.

6 Chandler & Aurora

In season 1, Chandler dates Aurora. He can't believe such a beautiful woman would date him. Of course, there's just one catch. She has a husband and a boyfriend already. They all know about each other. Chandler's fine with it and even starts dating her. At first, he loves the idea of this relationship. In fact, Ross agrees it's a great idea. Later, Chandler doesn't like it anymore and ends things. Ross doesn't understand why he broke up with her. It's a bit odd that Chandler would be fine with this and Ross would back him up.