content: always reach for the bill on a first date  Can I suggest an alternative? Don't spend money on a first date - at least, not unless you're already having a fantastic time. You want to meet up somewhere where you can chat, and you want to "next" her if there are any red flags at all. If she seems cool, go do something fun, but free. Go see a band play. If you're having an amazing time and it seems like you'll hook up, then maybe grab some food. But otherwise, don't do the dinner date thing. ...not until you've had sex. After you've had sex, fine, go ahead and take her to a restaurant.