What Music to Play When You Pick Her Up

“Play the songs she might not have heard before”
That pivotal moment when you’re on the way to her house to pick her up for your date will set the tone for the entire evening. If you’re nervous and freaking out before you even see her, it’s going to reflect on you later. A little bit is fine, but calm down. Put in your favorite tunes and psych yourself up. Who knows, she might enjoy what you’re playing… but then again she might not. What are you supposed to do? Having music on in a car is just natural, and if there’s a lull in conversation you want to be sure that you’re going to have something to fall back on so no one feels awkward.
Play a Taste of Your Music and See How She Reacts

“Start your date in the car itself”
Keep in mind: if you’re playing death metal or rap that has the word “pussy” in it 40 times, it may not make the best impression. You’re letting this girl into a sliver of your world. The car is where you actually spend a reasonably large amount of time, and it’s a representation of you. So is the music that it’s playing. Stick to the tamer side of things when you hookup your iPod. It might feel like a little bit of a cop out or like you’re trying to water down what you really listen to, but unless your genre is pop music, you’re going to be on a path that’s a little different from most people (and even then that’s not always true). Popular radio music will be a good starting point for both of you to connect to, so pick your favorite station and let them do the work. Otherwise always have a light mix at hand, so you can play the acoustic version of that death metal band.
Play Something Strange for a Good Conversation Piece
Are you in love with Huey Lewis and the News? Maybe Gogol Bordello is more your thing. While these are totally out there, if you’re into them, then there’s nothing wrong with that. Not everyone will have the same musical tastes, and most people are okay with that. Your light mix mentioned above might be a little bit easier to digest, but putting on something that you love and is totally left field for most other people will give an insight to you as a person and can act as a conversational piece. Have some info or stories lined up about the band that’s playing, and (depending on the distance) you might already have your whole car-contained conversation setup. Just make sure to dig around a little bit and see what strange stuff she’s into. If you met on an alternative dating site, she’s sure to have some interesting tastes.