Have a general idea about what you might do before you even ask about a date.
If you suggest "Maybe we can get together sometime," and you get a favorable response, follow immediately with "Great, how about next Saturday?" The idea is to move the conversation directly to the specifics, rather than stand there stammering like a simpleton.
Plan first dates to be able to talk and get to know each other for a brief time in a nonthreatening environment.
A rock concert is exciting, but too loud; dinner at an overly romantic restaurant can be too intense. Coffee? Good idea. Pick something that lets either of you easily slip away from an awkward first date.
Get tickets to a theater opening, a concert or a ball game.
Make sure it's something your date will enjoy. Then, call well in advance of your planned meeting, and say that you might be able to get tickets for a big event. Ask your date if he or she would be interested. If the response is anything less than wholehearted enthusiasm, sell the tickets to your brother-in-law.
If your first idea bombs, think of something else and remember that sitting and talking in a great environment is the whole idea. Acting beleaguered will get you nowhere fast. Your attitude is far more important than the activity.
Plan a picnic.
It shows your organizational skills, as well as your appreciation of romance. Pack wine, a luscious feast and dessert. Remember that you'll need to bring everything, including a blanket, bottle opener, cutlery, plates, cups and napkins (see 321 Plan an Outdoor Party and 322 Impress a Date).
Stick to mainstream activities while you get to know each other.
Until you know your date shares your tastes, keep the nude yoga classes and extreme rock climbing on the back burner. Granted, unusual activities can be a good way of filtering out those who have nothing in common with you, but they may also scare away qualified prospects.
Have a mental list of romantic spots.
If things are going well, suggest a visit to one of them. It needn't be elaborate and shouldn't be forced. A bar with a great view of the city always works, or even a visit to a swing set in a park.
- Keep your plan flexible. Chuck it altogether and improvise if something's not going well, or if it's going so well that you don't want to break the spell. Don't worry about sticking to a predetermined schedule that has you rushing from one event to another.
- If your plans wash out, don't get discouraged--learn from your mistakes. And remember, bad dates can be a source of great stories (see 208 Prepare a Speech and 334 Execute Best Man Duties).
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- Arrange a meeting or pickup time and don't be late. Leave yourself plenty of time so that you arrive relaxed. See 20 Never Be Late Again.