I am assuming that I am not the only rookie mom for whom leaving my child to be put to bed by a babysitter for the first time was scary. My kid never took a bottle, so I pretty much had to be there for a bedtime nursing for the first ten months. This feeling is the opposite of freedom, by the way.
Once your baby is reliably sleeping between 8 pm and midnight or beyond, you can resume the life you used to lead in restaurants and cafes by making dessert dates with girlfriends or your partner. This is the least stressful babysitter situation possible. Pretty much anyone is qualified to lay on your couch and watch TV while you enjoy a short evening outing, right?
Put your baby to bed the way you like. When you are confident he is asleep, head out to any of your favorite restaurants. Order dessert or a drink. Enjoy ambience. Leave.