My attempt to buy train tickets online failed as you know. So, I decided to go offline and do it again.
Bearing in mind that I do speak Russian but will pretend I don’t and I really need a ticket for Wednesday I decided to make a little cheat sheet to make sure I eventually manage to buy a ticket.
First, you go to the English version of the site www.poezda.net and click Detailed Search. Please keep in mind that transliteration of the cities is quite weird on this site. I expected to find Kharkiv under letter K, but it is Harkov for some reason.

I’ve got my selection:

And have a little cheat sheet with my choice:

Point of destination at Kharkiv Train Station (they used to have a proper sign “International tickets”, but now it’s undercover of airplane tickets desk):

I really hope I won’t need to pull my cheat sheet here.
Come in.
No customers, behind the glass the one and only lady in the uniform.
She nodded to my greeting and there started the one the most absurd dialogs in my life (English translation is in square brackets):
-I’d like to buy a ticket to Dzhankoi please.
- Джанкой – Харьков? [Djankoi- Kharkov?]
- no, no. Kharkov to Dzahnkoi. Train number seventeen.
- Когда? [When?]
- sorry?
- day?
- Wednesday.
The uniform lady makes indefinite lip movement. And I take out my cheat shit.
- Так, среда. [all right, Wednesday] First class? Second class ?
Now I realize I have no idea how does she distinguishes classes and I don’t want to buy overpriced ticket, so I say “compartment, please. Kupe”.
- how much is it?
- Не знаю, надо смотреть. [I don't know, I need to check it]
She taps something on her keyboard and says:
- нету! Поняла? [No tickets! Do you understand?]
I don’t understand. And she takes my little cheat sheet and replies, underlying the word ‘Moscow’:
- Завтра. Он московский, from Moscow. [Tomorrow, the train is from Moscow]
- Tomorrow?
- Приходи tomorrow. Понимаешь или не понимаешь? [Come again tomorrow. Do you understand or you don't?]
All her replies were very loud and clear and in Russian. I know this syndrome, when an opponent thinks that you are really deaf if you don’t understand foreign language.
She wrote 21/02 on my paper and I said thanks and bye.
Conclusion: ticket office clerk will try her best to sell you a ticket using only Russian and some bits of survival English. You should not expect any extensive help on finding you routs and answering questions. This reminded me of Spanish experience : even if a person answers “un poco” to your “do you speak English?” you can hope this person understands English but unlikely would say a word in it. On the other hand, why this person is working at International tickets office, I wonder? Was it a magic line ‘basic English’ in her CV made it happen or she has some hidden precious working qualities I haven’t been lucky to unfold?
If I were you I would ask locals to help with buying train ticket or would enroll to Russian or Ukrainian language course. Or made a cheat sheet just like I did. Or quoting
Lonely Planet Ukraine guide:” Ticket clerks probably don’t speak English, so get a local to write down what you need.”
PS: Meanwhile Ukrainian Railroad Network has got a new funky site in English (with Facebook and twitter and what not) – I tried to use their travel planner, but ‘computer says no’, because it’s a test version and your attempts to plan anything can hang the server.