Το βράδυ παίζουμε σκάκι και ένα επιτραπέζιο παιχνίδι με την παρέα μου, και ο αντίπαλός μου πάντα γελάει.

Το βράδυ literally means “the evening” or “the night (time in the evening)”.

In Greek, it’s very common to use the definite article (το, η, ο) with time expressions to mean “in the …” in a general or habitual sense:

• Το πρωί – in the morning
• Το απόγευμα – in the afternoon
• Το βράδυ – in the evening / at night

So Το βράδυ παίζουμε… can mean:

• “In the evenings we play…” (habitual), or
• “Tonight we’re playing…” (if the context is about tonight)

The article Το is neuter singular, agreeing with βράδυ (a neuter noun).

In Greek, the subject pronoun (εγώ, εσύ, αυτός, εμείς, etc.) is usually dropped, because the verb ending already shows the subject.

• παίζω – I play
• παίζεις – you (sg.) play
• παίζει – he/she/it plays
• παίζουμε – we play
• παίζετε – you (pl.) play
• παίζουν(ε) – they play

So παίζουμε on its own clearly means “we play / we are playing”.

You could say Εμείς παίζουμε σκάκι…, but εμείς is normally added only for emphasis, like “We (as opposed to others) play chess…”.