Would you like to go out with me?
Do you mean "will you go out with me?" it's "salirás conmigo?"
"Quisiera usted salir conmigo" translates to "Would you like to go out with me?" in English.
"Vas a salir conmigo" means "Are you going to go out with me?" in English.
It means "will you go out with me"
"Quieres salir conmigo" translates to "Do you want to go out with me?" in English. It is a common way of asking someone if they are interested in dating or spending time together.
if you would like to go out with me. (unless you intended for an accent over the i in si, in which case it would be "yes, you would like to go out with me")
I think you mean conmigo it means [with me]
literally "and I want when you (formal) speak with me in Spanish" - was this a native speaker?
I think that you're missing a verb. -Literally translated it means "I know that you (formal) no/not marrying me". Do you wanna say "I know that you don't want to marry me"? "Sé que Ud. no se quiere casar conmigo/sé que Ud. no quiere casarse conmigo"?????
"you are way too sweet for me, i miss going out with you guys"
Quieres dormir conmigo? You could also say Quieres acostarte conmigo.? ( do you want ) or Te gustaria acostarte conmigo? ( would you like) Be aware that acostar has a more intimate (sexual|) suggestivness so if you don't mean to say it in that way then Quieres dormir conmigo? is the best to use
Do you want to (go out)/(leave) with me playing jugando is Playing a game or playing like a child plays. It is not playing a musical instrument or in a band.