I took one former gf to a strip club twice. I suppose the best way to broach the subject is when you're already out for the evening, and near a nice club. Maybe just ask her if she's ever been or ever thought of going. I think just about anyone would go once. Once your there, things get easier. Splurge on champagne and make her comfortable by not acting like a frat boy. Then, pay attention- the dancers will pay special attention to her and help put her at ease- remember which one she seems to connect with the best- and offer a more private experience. Most dancers between performances will give lap dances for about $30-$40. This is money well spent. Sit back, relax, and watch.