Instead keep the convo moving by making funny observations.("Do you ever accidentally make eye contact with the people stopped next to you at a red light? ") Don't worry about silences — you can always default to talking about what's playing on his i Pod.If the Internet is good for anything—and, actually, it’s good for lots of things—it’s good for finding a needle in a haystack.
Keep your cool and calm his jitters by giving him a warm hi and a quick hello hug.
Then make a joke that acknowledges the weirdness ("Full disclosure: I changed three times! (If he honks from your driveway, wave him in for just a minute while you grab your purse and jacket.)Your instinct may be to ask a bunch of questions to get him to open up, but that can feel like a college admissions interview.
Since he picked the music, he'll have stuff to say about it.
If you think he might pick up the check or don't know how much food to order, ask him what he's getting and choose a dish around the same price. If he really insists on paying, thank him and say you'll buy him ice cream next! Don't rush out of the car when he drops you off — move closer to him and keep eye contact. Play it cool and let him reach out to you: Texting first can seem overeager.
I know people who really get into exactly the time they should show up.