It’s Still You and a Gal
So you have paid to have someone join you for the evening for some fun and adventure, but that does not mean that all the social dynamics you normally have to deal with are out the window. It is still you and a real woman (unless your have ordered something different) out on the town. To optimize the fun for your evening, the following steps will help you to break the ice, eliminate as much awkwardness as possible, and increase your chances that your night out will be spectacular!
Don’t worry about starting the conversation, either start it or don’t. Silences can be awkward, but given that everyone involved wants the evening to go well, you can always ask her to start things up. A simple, “So why don’t you tell me something about yourself,” will usually let her know that you want her to start. If you are going to compliment her, don’t compliment her on her looks –everyone does that. Compliment her on her clothes, or her style, or something that is unique. The trick to successful complimenting is to be honest. Find something you like and say so. Don’t compliment her dress if you hate it, because she will be able to tell.
Gentlemen Get Laid
Remember that gentlemen get laid more often than jackholes. Even given the financially rooted foundation of this encounter, it is important that you act respectfully. You are paying for her time, not for her.
Friendly But Not Personal Subject Matter
What makes this night different from a night with someone you met at work is that the depth of personal information that you and your date are willing to share might not be the same as in other situations. Talking about family may make your date a bit uncomfortable, so use your best judgment and ease into this type of topic. If you are comfortable talking about yourself and your life, go ahead, but don’t expect her to do the same.
Like and Dislikes
Talking about the type movies you like, the sports you like, and what you like to do with your free time are great topics. Allow her to choose the topic, then you don’t have to worry.
Of course the topic of sex and sexuality is likely to come up. Remember to be respectful and polite, and to respect boundaries. A little naughty talk first before getting into anything really raunchy will allow you the opportunity to see how well received such language is. If she is not digging it, back off a bit.
When the time comes to get busy (and by ‘busy’ I mean have sex!) remember to be respectful. You are free to lay out to her exactly what you expect and are interested in, but remember that she is free to refuse whatever she is not willing to do, and she may think you are a cop. Never mention money. Frank open discussions are better than misunderstandings during or after sex.