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QUICK ANSWER
"Con qué jugabas" is a form of "con qué jugabas", a phrase which is often translated as "what you played with". "Con quién" is a form of "con quién", a phrase which is often translated as "who ... with". Learn more about the difference between "con qué jugabas" and "con quién" below.
con qué jugabas(
kohn
keh
hoo
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gah
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bahs
)A phrase is a group of words commonly used together (e.g., once upon a time).
a. what you played with (short or defined period of time)
Me gustaría saber con qué jugabas si no tenías juguetes.I'd like to know what you played with since you didn't have any toys.
b. what you were playing with (long or undefined period of time)
No me digas con qué jugabas. Déjame adivinar. ¿Era un coche de juguete?Don't tell me what you were playing with. Let me guess. Was it a toy car?
a. what did you play with (short or defined period of time)
¿Con qué jugabas cuando eras niño?What did you play with when you were a child?
b. what were you playing with (long or undefined period of time)
¿Con qué jugabas anoche? Hacías mucho ruido.What were you playing with last night? You were making a lot of noise.
con quién(
kohn
kyehn
)A phrase is a group of words commonly used together (e.g., once upon a time).
a. who ... with
¿Con quién fuiste al cine el fin de semana pasado?Who did you go to the movies with last weekend?
b. with whom
¿Sabes con quién vas a presentar la propuesta?Do you know with whom you will be presenting the proposal?
