Perhaps one of the biggest headscratchers of Friends was how Ross not only managed to date multiple amazing women, but the fact that he was also married multiple times. Ross didn't come across as the greatest friend, let alone a great boyfriend or husband.

Furthermore, there were problems and things that just didn't make sense in pretty much every single one of his relationships. For the most part, each could probably be explained by the fact that Ross was one of the main characters and therefore fans were expected to be on his side. Over the course of 10 seasons of Friends, Ross had several meaningful relationships (and he didn't even marry every woman).

There was, of course, Rachel, and everyone knew that they would be the endgame couple. Still, so much of their relationship — including the fact that they ever reunited after he was unfaithful — just didn't make sense. There was also Emily, and really nothing made sense about their relationship, even though the strangest part of it has to be the one-eighty the series did with her character from their wedding onward. Then there was the fact that the women who Ross dated started off being completely normal, but soon ended up being the bad guy, much like what happened with Emily, by the time their relationship was over.

With that said, here are the 25 Things That Make No Sense About Ross' Relationships On Friends.

How Long Ross Knew Emily Before They Got Engaged

The series introduced Emily as someone Rachel was supposed to spend time with, but Rachel hoped to spend her evening with Joshua instead. Because of this, Rachel asked Ross to do her a favor and go out with Emily.

The next thing everyone knew, Ross and Emily were spending the weekend together. She was even flying back and forth from England to see him. When it came time to move forward, they jumped from talking about moving in together to becoming engaged. They'd only known each other for six weeks.

Ross Broke into Mona's Apartment for a Shirt

When Ross couldn't find his "faded salmon color" shirt, he realized it was at Mona's. Rachel suggested he just ask Mona to give it back. However, Ross said they didn't end on good terms.

For some reason, he thought a better idea would be to use a spare key to enter her apartment without her knowing. She returned, with a date, and he hid, but she saw him when he tried to take his shirt back. It just didn't make sense that Ross thought breaking into her apartment was a better option than just calling her and asking for his shirt back.

Ross Ignored His Date to Talk to Carol

Ross' tendency to pay more attention to an ex-girlfriend or ex-wife went back to the early seasons of Friends. He was on a date with a woman for Valentine's Day when he ran into Carol — and he spent the evening talking to his ex-wife and ignoring his date. His date, understandably, left.

However, this was just an unfortunate flaw and pattern of his, one that showed he sometimes got stuck in the past. Rather than focusing on someone who could be part of his future, he often fell back on what he knew.

Why Did Emily Go Through With the Wedding?

During Ross and Emily's wedding, he said Rachel's name instead of his bride's. Season 4 ended on a cliffhanger, and it would have been completely understandable if, when season 5 began, Emily left him at the altar. Instead, though, Emily actually went through with the wedding.

However, she locked herself in the bathroom after, went out the window, and skipped out on the reception. Ross ran around trying to find her and reach her, but she refused to speak with him. Emily's actions made sense, but why did she even bother marrying him? Why was she even willing to try to fix the marriage (albeit with ridiculous conditions)?

Why Didn't Ross Ever Take Responsibility for being with Chloe?

When Ross and Rachel were dating the first time, she asked for a break. When they spoke on the phone later that night, he heard Mark in the background and assumed she was going to be with him. Ross then was with another woman, Chloe, that night and argued it wasn't a big deal because they were "on a break."

However, Ross never truly took responsibility for that and even refused to when Rachel asked him to before they would get back together a season later. Because of this, that reunion never happened. The series treated "we were on a break" like a joke, even in the series finale when the couple did finally reunite.

Ross Dated One of His Students

Ross dated one of his students and at first thought it was just frowned upon but not against the rules. Then, he found out it was against the rules and he could lose his job. However, neither he nor Elizabeth considered that to be as big a deal as they should have.

Remember when Ross faked an accent to try to get the job at the university? It's surprising he didn't care more about doing everything he had to in order to keep his job. That doesn't even take into consideration the time that Ross and Elizabeth spent together in his office. It was just all a mess.

Ross Never Respected Rachel's Career Choices

Ross and Rachel are supposed to be the couple that everyone roots for while watching Friends. Viewers are supposed to want to see them end up together. Therefore, shouldn't they respect and support each other, both personally and professionally?

Ross didn't. He interrupted Rachel's work life because of jealousy in season 3, and he even fell asleep during a lecture he insisted on attending with her. Then, in season 10, when he didn't want her to move to Paris, he took it upon himself to get her old job back for her without even asking her if she wanted it.

The Timing of Ross Wanting Rachel Back in Season 10

Ross and Rachel were always going to end up together. That was pretty obvious. Because of this, Friends didn't seem to put much effort into getting them back together in the final season.

Because there was no real build-up to their reunion, it really seemed like Ross only decided to get back together with Rachel — and affect her career — when she was moving to Paris. Yes, he could have realized he was running out of time, but he also didn't even consider a long-distance relationship. What he wanted was to be with Rachel, in New York, where he had his job. Yet, fans were supposed to root to see these two together.

Why Was Emily the Bad Guy When Ross Messed Up?

When Ross and Emily got married, he was the one to mess up and say the wrong name (Rachel's). It took a while for Emily to respond to his attempts to contact her, and when she did, she came up with conditions for their reunion. Those terms included moving to a new apartment, getting rid of anything Rachel had touched, and never seeing Rachel again.

Yes, the conditions were ridiculous, but everyone seemed to forget that Emily was a woman who had been very hurt and embarrassed on her wedding day. Ross said his ex-girlfriend's name in the middle of the ceremony, in front of all of her friends and family. However, the show pretty much forgot about that and acted like Emily was a bad person.

Ross' Jealousy About Mark

When Ross and Rachel dated the first time, he was very jealous of the time she spent with her coworker, Mark. In order to make sure Mark was constantly reminded of the fact that she had a boyfriend, Ross sent Rachel countless gifts proclaiming his love. He even sent a barber shop quartet to sing about his love. It was more than a bit much.

How is it that Ross thought any of that was okay? He had no reason to act as insecure in their relationship as he did, yet he constantly had a problem with Mark — even when he showed up seven years later and saved Rachel's professional life after she lost a job.

The Pros and Cons List About Julie and Rachel

Just as Rachel realized she might have feelings for Ross, he started dating Julie. Then, Chandler suggested that he make a pros and cons list about the two women when he was struggling with his feelings for both.

Ross went along with it, and some of his entries for Rachel were disrespectful. It was even rude of him to say that Julie's con was that she wasn't Rachel, though that was a pro for Rachel. How did he think that making such a list about women he was dating or wanted to date, even if he never intended for them to see it, was okay?

His Treatment of Carol

Ross' sadness about the end of his and Carol's relationship made sense, at least in the beginning. However, he never really seemed to let that go and really should have treated her better. She was, after all, his (first) ex-wife and the mother of his son.

They had history, and Ross really should have taken that into account during their interactions. At one point, he even considered moving to England with Emily, not caring about how that could affect Carol and their son. Furthermore, there was a legitimate reason for the end of his and Carol's relationship, and the way Ross acted about Carol being gay was, honestly, awful.

Why Did Rachel Ever Want Him Back?

When Ross and Rachel dated the first time, the relationship ended because he was with someone else. He thought their "break" was a breakup and she was going to be with Mark. However, that didn't excuse his actions.

Rachel was hurt and broke up with him when she found out. Then she realized she still loved him while he was with someone else and kissed him. Why did she ever want to get back together with him or take him back when he showed a pattern of infidelity, which she clearly had a problem with?

He Didn't Really Care About Being With Someone Else on the "Break"

Once Ross realized that he and Rachel hadn't broken up and she wanted to work things out, his immediate concern wasn't that he was with someone else, but that Rachel might find out what he did.

He hurried around to make sure that it wouldn't get back to her, but, of course, it did. He even told her he did just that, which didn’t help his case. It seemed like he didn't care as much as he should have about being with someone else when he and Rachel were still technically together.

Did Ross Ever Truly Like Bonnie?

When Ross was dating Bonnie, Rachel realized that she wanted to get back together with him. They kissed and were on their way to reuniting when Ross remembered that he had to break up with Bonnie first.

However, he didn't even seem to really care about her. It was one thing to prefer to be with Rachel, but he pretty much seemed to forget that Bonnie existed once Rachel was an option again. It just didn't make sense. Bonnie was also Phoebe's friend, yet the series also seemed to forget about that once Ross and Rachel were a possibility again.

Everyone Forgot That He Agreed With Emily's Conditions

After Ross said Rachel's name at his and Emily's wedding, his new wife was upset. Emily eventually agreed to work on their relationship and come to New York, but only if Ross agreed to some conditions, including not seeing Rachel. Ross agreed.

However, once Ross decided to stand up to Emily and they got divorced, everyone seemed to forget about that fact. Why did Ross just get a pass when he was willing to not see one of his friends? Emily was made to be the bad guy in the situation, and everything Ross did that was wrong was promptly ignored or excused. It just didn't make sense.

Did Ross Ever Call Caitlin?

Friends made the fact that Ross was flirting with Caitlin, the woman who delivered their pizzas, into a big deal. It was the plot for an entire episode. Rachel even went and got her phone number for him.

However, fans never found out if he called her or if anything came of it. It just didn't make sense that so much time was spent on Ross' poor attempt to flirt to Caitlin that there couldn't be just one line in another episode to let fans know what happened there.

Why Didn't Ross Just Admit He Didn't Read the Letter?

When Ross and Rachel were on the verge of getting back together, she wrote him a long letter. Yes, the length (18 pages, front and back) was a bit much, but she clearly had a lot to say, and he should have read it all considering how much he cared about her.

He fell asleep reading the letter, and rather than being honest and saying that he'd read it that morning, he lied. He told her that he had read it and even luckily provided the answer she wanted regarding a question in the letter. Why did Ross think lying was a better option than being honest?

He Thought He and Rachel Could Stay Married

After Ross and Rachel got married in Vegas, he told her that he'd take care of the annulment. However, when he found out they'd have to get a divorce, he didn’t want another one to his name. Instead, he thought he could hide the fact that they were still married from Rachel — and then convince her to stay married when she learned the truth.

How did Ross think either of those were realistic options? Neither was fair to Rachel, not that he cared about that fact. It should have been a bigger deal than it was, yet Rachel seemed to just forget about that once the papers were signed.

Why Wasn't He More Concerned About His Relationship With Elizabeth Affecting His Career?

When Ross was dating Elizabeth, he met her father. Paul didn't like that his daughter was dating Ross and threatened to tell the university about their relationship. It was against the rules, and it could have cost Ross his job.

Rather than being concerned about this fact, though, Ross continued to see Elizabeth and even managed to get out of any trouble because he saw Paul during an embarrassing moment. However, why didn't Ross worry more about losing his job? He treated it like a joke, even though what was clearly a temporary relationship could have cost him something important.