“How similar are Russian and Ukrainian?” is a frequently asked question. As someone who previously knew neither language and am now studying Russian at a B2 level, I can give a good first-person answer to this question. I will just explain how I felt at each step of the process, and feel now.
4 years ago, any language using Cyrillic looked the same to me. That of course does not mean they are identical, it just means the uninformed viewer doesn’t recognize the differences. So Serbian, Russian, Ukrainian and Bulgarian would all look the same to me. Just like Chinese and Japanese still look the same to me.
Then, while sitting in my hospital dorm, I decided to learn the Russian alphabet. After this point I could notice some differences, and start telling the languages apart.
My auditory skills developed more or less the same in principle. After watching some Soviet movies with English subtitles, even when I couldn’t understand the dialogue, I could start to recognize Slavic languages when I heard them.
To give an analogy of how this process went, it might be meeting a person of a different race or ethnicity for the first time. You can tell how he’s different from you and that’s it. Then when you meet a second person from that group, you can see the similarities, but not be able to tell them apart. Then after you interact with enough of those people you can start to easily tell them apart, and recognize different sub groups and nationalities that were previously invisible to you.
And to give you an idea of where I’m at now; I’m studying at the B2 level and can read simple hard news stories somewhat competently (hard news is deliberately written at a 3rd grade level to be easily understood). Fictional prose is much harder of course. In-depth conversations and watching movies at normal speed without subtitles is still very tough.
So here’s an example. This morning I came across this math problem from a Ukrainian children’s textbook:
This problem has names, pronouns and military terms that are basically the same in Russian. And even when I don’t immediately recognize the verb, I can guess through context. So I could infer that this paragraph roughly says the following:
“Dmitry has 10 shells for his battery. Then he was joined by two of his friends. They had 5 shells each. Then the mean moskals stole 4 shells. How many shells does Dmitry and his friends have for the defense of Ukraine?”
Checking my answer, I was roughly correct, at least correct enough to be able to solve the math problem if given to me.
But that’s a simple math problem. If it was fictional prose full of flowery language and complex sentence structure I would likely not understand it at all. And listening to someone talk without visual context is ten times harder.
And note the screenshot from Yandex translator is for illustrative purposes. Even the best “AI” is notoriously unreliable. You need to use your own brain and look up any individual word you don’t know. Fortunately, Russian and Ukrainian have the same noun cases. So even if the message itself is unclear, the subject object relationship is apparent.
Here is a trickier example from the Ukrainian Ministry of Defense today:
A lot of words here I don’t recognize and couldn’t even begin to figure out without looking them up. But fortunately there is a picture which answers some of my questions.
This message very roughly says
“The Reserve+ app is available for (conscription exemptions?) for people with a handicap, students, and those with 3 or more children.
“They must select (exemption?) and then the category of (exemption?).
“Something something from the results. If the data of something is not found, turn to the administration of social defense of the people near the place of residence.”
So I was able to fumble my way through this simple message. Though the third paragraph was mostly not understood, I got the general message. My ability to understand Ukrainian is most limited by the fact that I don’t study Ukrainian, and my Russian vocabulary is very small. If I knew more Russian, this text would come to me easier.
Ian Kummer

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This was quite interesting.
Can you keep a conversation with a Russian native with relative fluency?
I knew a Dutch chap who was working as a teacher of English as a foreign language in Zelenograd. He told us that, as he knew Russian very well, he had been asked if he could run a specialist course for Foreign Ministry officials to learn Ukrainian by the university where he had worked back home. Being a confident gentleman, he said yes.
He based each lesson on an excerpt of a newspaper or magazine, looked up all the words before the seminar then “taught” his students. He was happy to admit to us that he could barely string together a sentence in Ukrainian and nor could his students, but they all knew Russian and it was more than enough to allow them to think they could follow the public debate in the Ukrainian press back in the 1990s, so the Foreign Ministry was happy.