Gateway Date

A first date where you are not yet in a relationship where you are assessing the situation. A date where you decide if you are interested.

Yo you guys dating?
Nah but I got a gateway date tomorrow night.

Gateway Date

When a guy hangs out with a girl who is in a relationship in hopes that when or if they break up, she comes to him.

Buddy: I'm going on a gateway date with this girl tonight.
Guy: Oh yeah? So she has a boyfriend?
Buddy: Yeah, but you know she doesn't talk about him at all. I'm pretty sure that means I can slay.
Guy: Alright good luck buddy. Don't get your ass kicked.