How is this understood in German, and how Old are the "Kinder"?

Literally:

Do you want to go/come with me? yes/no/don't know

Figuratively:

Do you want to go (out) with me?

Do you want to date/be my bf/gf?

ps - it's a long, long time since I've been confronted with this scenario (if it's the second one), so likely the expressions have changed

Well, "Do you want to go with me?" is used, yes, but I don't know about current youth and whether they still pass notes to each other in school. Isn't that a little bit of 20th century nostalgia? Don't they just use whatsapp or something? ;-)

Edit: In practice it's probably more like "(You) Wanna go with me?"

Echt? Meines Wissens wurde der letzte handeschriebene Zettel Anfang der Nullerjahre gesichtet.

#7: Zettelchen ...nicht über grundlegende Liebesfragen.

Anstelle grundlegender Liebesfragen werden heute wohl eher abseitige Liebespraktiken (tele)kommuniziert....

;-)

In my BE (primary) school years. By secondary school, people usually sent

a friend or asked themselves.

N.B.: To go with someone had much further-reaching connotations.

"Willst du mit mir gehen?" definitely means more than just go out. It means "Do you want to be my boyfriend/girlfriend?"

Meiner persönlichen Wahrnehmung nach ist das Zettelchenschreiben "Willst du mit mir gehen? Ja/Nein/Vielleicht [mit Ankreuzkästchen]" aber sowas von "Achtziger" ;-)

Machen die Jugendlichen von heute sicher nicht mehr. Die haben Whatsapp.

"Going out with someone", in BE, means being their girlfriend/boyfriend.