Basically, just making conversation. No movie. No double-date. Just one on one.
No previous friendship.
Most Helpful Girl
Entertain? dating and just being someone isn't about "entertaining" them it's about getting to know each other, having fun with each other and putting in the same effort to build the trust, where do people get these ideas? you can't just entertain someone it's more complicated than that. I really think just talking for hours on end when you don't know each other would be rather boring too and if i dated a guy i certainly wouldn't just want to talk and talk id want to do something with him too, something fun like bowling, pool, something where i can have fun but still interact with him at the same time, movies are terrible for dates i don't know where people get the idea because it's not exactly interactive, try doing something fun with them too where your still talking and you can talk for a bit before that and then once the day has ended if you hit it off you can stay awake and talk all night :). Just create fun and good memories for your date to think positively about you.1