Learn Hardcore Russian: Я тоже люблю шутить, но стараюсь чувствовать, когда можно, а когда нельзя. - I also like to joke, but I try to feel when it is allowed and when it is not.

тоже usually adds something about the same person or thing and often has a slightly more informal, conversational feel:
- Я тоже люблю шутить. – “I also like joking (just like you / like someone else).”
также is more neutral/formal and often used when adding another fact rather than emphasizing similarity with someone:
- Я люблю шутить, а также смотреть комедии. – “I like joking and also watching comedies.”

In your sentence, you’re aligning yourself with someone else who likes to joke, so тоже is the natural choice.

Why is люблю шутить used instead of something with нравится, like мне нравится шутить?

Both are possible, but they’re not identical:

люблю шутить = “I love / I like to joke.”
- любить + infinitive expresses a habitual preference, something you like doing in general.
- It sounds more active and personal.
мне нравится шутить = literally “joking is pleasing to me,” i.e. “I like joking.”
- нравиться is more like “to appeal to” someone.
- With activities, it’s used, but a bit less often than любить + infinitive for general habits.

In this context, Я тоже люблю шутить sounds very natural and idiomatic: “I (too) enjoy joking / I like making jokes.”

Why is шутить in the infinitive and not шучу or some other form?

Because in Russian, after любить (and most other verbs of liking/wanting), you normally use the infinitive to express “like to do something”:

люблю шутить – “I like to joke.”
люблю читать – “I like to read.”
люблю готовить – “I like to cook.”

If you said я шучу, that would mean “I am joking / I joke” (right now or in general), not “I like joking.” So:

Я шучу. – “I’m joking.”
Я люблю шутить. – “I like joking.”

What aspect and form is шутить, and why not пошутить?

шутить is an imperfective infinitive.
пошутить is a perfective infinitive.

Imperfective (шутить) is used for:

general, repeated, habitual actions (to joke in general),
ongoing processes.

Perfective (пошутить) is used for:

a single, complete instance (“to tell a joke once”).

In люблю шутить, we’re talking about a general habit (“I like joking (in general)”), so the imperfective infinitive шутить is the correct choice.
If you said люблю пошутить, it would mean more like: “I like to crack a joke (now and then / on occasions),” slightly more about individual acts.

What exactly does стараюсь mean, and how does стараться work grammatically?

Стараться is a reflexive verb meaning “to try / to make an effort.”

я стараюсь – “I try / I make an effort”
Pattern: стараться + infinitive
- стараюсь чувствовать – “I try to feel/sense”
- стараюсь приходить вовремя – “I try to come on time”

It often carries the nuance of conscious, good-faith effort, sometimes more positive than пытаться (“to attempt”), which can sound more neutral or even a bit desperate in some contexts.

So но стараюсь чувствовать… = “but I try to sense / I make an effort to sense…”

What does чувствовать mean here? Is it physical feeling or emotional?

Чувствовать can mean:

to feel physically – чувствовать боль (“to feel pain”)
to feel emotionally – чувствовать радость (“to feel joy”)
to sense / to have a feel for something – more intuitive, “to pick up” situations.

In this sentence it’s meaning (3):

стараюсь чувствовать, когда можно, а когда нельзя
≈ “I try to sense / have a feel for when it’s okay (to joke) and when it’s not.”

So it’s about social sensitivity and tact, not physical sensation.

Why is there a comma before когда: …стараюсь чувствовать, когда можно…?

In Russian, clauses introduced by когда (“when”) are usually subordinate clauses, and they are separated by a comma from the main clause.

Structure here:

Main clause: (я) стараюсь чувствовать – “(I) try to sense”
Subordinate clause: когда можно, а когда нельзя – “when (it’s) allowed and when (it’s) not”

So you must write:

…стараюсь чувствовать, когда можно…

The comma shows that когда можно, а когда нельзя depends on стараюсь чувствовать.

Why is there no verb after можно and нельзя? What is actually meant?

Russian often omits repeated words when they’re obvious from context.
Here, the infinitive шутить (“to joke”) is understood but not repeated:

Full, explicit version:
…стараюсь чувствовать, когда можно шутить, а когда нельзя шутить.
Natural spoken/written Russian drops the second шутить (and often the first too, if context is crystal clear):
…когда можно, а когда нельзя.

So the meaning is:

когда можно (шутить), а когда нельзя (шутить)
– “when it’s okay to joke and when it isn’t.”

English often needs to repeat “joke,” but Russian is comfortable leaving it implicit.

What exactly do можно and нельзя mean here grammatically?

Можно and нельзя are predicative words used in impersonal constructions:

можно – “(it is) possible / allowed / okay”
нельзя – “(it is) not allowed / must not / not okay”

Typical pattern:

(кому) можно / нельзя + infinitive
- Мне можно идти? – “May I go?”
- Тебе нельзя шутить над ним. – “You mustn’t joke about him.”

In your sentence, the person is understood (the speaker and people in general), and the infinitive шутить is omitted but obvious:

когда можно (шутить) – when it’s acceptable to joke
когда нельзя (шутить) – when it’s not acceptable to joke

There is no explicit subject like “it”; the sentence is impersonal, which is very common in Russian.

Why do we have both но and а: …но стараюсь чувствовать, когда можно, а когда нельзя? What’s the difference between но and а here?

They connect different types of contrasts:

но = “but” – contrasts your liking with your restraint:
- Я тоже люблю шутить, но стараюсь чувствовать…
  = “I also like to joke, but I try to sense…”
а here contrasts two alternatives: when it is allowed vs when it is not:
- когда можно, а когда нельзя
  ≈ “when it is allowed and when it is not.”

Some nuances:

но typically introduces a stronger opposition (“X but Y”).
а often marks a contrast or alternative, sometimes where English might use “and / but / whereas.”

You could theoretically say когда можно и когда нельзя, but и is more neutral (“and”), while а highlights the contrast more clearly and feels more idiomatic here.

Could I say Я люблю тоже шутить or Я люблю шутить тоже instead of Я тоже люблю шутить?

Native speakers would almost always say:

Я тоже люблю шутить.

Putting тоже after люблю or at the end is possible but changes the feel or sounds off in this short sentence:

Я люблю тоже шутить. – can sound clumsy; in some contexts it might stress “I love to joke too (among other things I love to do).”
Я люблю шутить тоже. – often sounds slightly unnatural or overly emphatic; you’d expect more context:
Я люблю шутить тоже, но…

In your sentence, the goal is: “I also (like you / like them) like to joke.” The most natural way to express that is:

Я тоже люблю шутить. – focus on “I, too.”