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As a Mistress of Knowledge here in Hampton Roads, it has come to my attention how miserable most men are at planning a decent date. I have learned this purely from observation, because of course my dates are always wonderful and romantic and embodied perfection. I am certainly not speaking from personal experience. However, I have conferred with some of my co-Mistresses of Knowledge throughout the state, and we have found that this is not merely a problem in this area, but all across the land. So I, Mistress of Knowledge, Hampton Roads Chapter 239, have decided to compile a guide for those poor souls who cower in the face of non-chatroom dating.
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Guide Installment #1 – The First Date, part 1

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Meet Someplace Neutral – Either a location midway between your places of residence, the place you will be going for your date, or a pre-date coffee place. Offering to pick her up at her place can be scary and stalker-like. She might not want you to know where she lives yet. Count yourself lucky if you’ve simply got her phone number. Try for a place where you can hang out if the conversation is flowing, but you can easily leave if it’s not. 

Suggestions: coffee shop, mall, park (daytime only)

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Give ‘em Something to Talk About – Have something that will provide a conversation topic. Let’s face it, on a first date, there are going to be awkward pauses. Keep them to a minimum by making sure there’s an easy, non-controversial topic to discuss. If the plan is dinner and a movie, reverse that order so that if the dinner conversation wanes, you can simply talk about the movie. That can also provide a starting place for other conversations. Unless you’re fairly sure a friendly debate won’t turn ugly, avoid hot topics like politics and religion.

Suggestions: movie/show before dinner, walking tours, museums

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Get Busy – Having an activity can work just as well to cover those awkward pauses. When you’re both doing something, the silence becomes comfortable instead of weird. Especially if you already know something you both are interested in doing. If you have no idea what your date likes to do, pick something most people generally enjoy. Definitely pick something you would enjoy too. If you’re not having at least a tolerable time, you won’t be good company at all anyway. Most people will be fairly open to your choice as long as it’s not something extreme like sky diving or something. But hey, if you think sky diving would be good, be sure to ask first if he/she would like it too.

Suggestions: carnivals/festivals, mini-golf, pool and darts, craft/activity classes

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Originality Counts – Although I previously mentioned the ‘dinner and a movie’ date, it’s not the most original idea in the world. Ladies can be charmed by creativity and thoughtfulness. Meeting for coffee is great, but try to avoid over-visited places that everyone has gone to before. Some of the best dates I’ve ever been on were at a sparsely-populated hole-in-the-wall. Generic chain restaurants are not your friends at this stage in the game. But be careful… hole-in-the-wall should not mean scary-dive-that-has-crimes-committed-in-the-back-room.

Suggestions: I’m afraid I have to leave that up to you.