First Dates: How well do you know them?
People you Know
This could be a date with the guy from your coed softball team. You’ve been chatting with him for months now, have seen him interact with the other players, and know he’s not a complete lush at the post-game celebrations. You’re comfortable with this guy. On the other hand, she may be a friend-of-a-friend, someone you’ve been talking to at all the parties for a while and she’s recently become single again. You’re pretty sure she’s not high-maintenance or crazy. Some say you never truly know anyone, but with these people you probably know enough. So which date do you choose?
These dates are the easiest because they provide a lot of flexibility. You don’t want to get overly romantic or complicated, because that just comes across as trying too hard and maybe a little needy. But your options run the gamut from a simple picnic at the beach, to off-roading, a cooking class, going to a football game, or sailing. The reason you have all of these options is that you’re familiar enough with this person to leave out the escape routes, and both of you are already invested enough in the relationship to splurge a little and just focus on having fun.
Don’t get too comfortable though, it’s still a first date and you should try for casual and relaxed. Dates to avoid are ones that take a lot of effort to pull-off or are overly intimate like the Chinese lantern picnic, watching the moonrise, or a hot stone massage (did I have to say it?). Your date will love this stuff a few weeks down the road, but right now it’s overwhelming. Also, even though you know this person, have the date on neutral ground. Don’t invite them over for dinner or to watch a movie, not only does it lack imagination but they’ll wonder if you’re thinking about sex. Which of course you are, but not this early in the relationship. Control yourself.
People you Know a Little
So who qualifies as a person “you know a little” exactly? Well, these are the people you’ve met casually around town; maybe someone you met at a party, a bookstore, or chatted it up with at the park. You’ve spent an hour or two getting to know a little bit about each other, but more importantly you’ve logged some face-time and have picked up on all of those non-verbal cues like mannerisms, eye contact, and facial gestures. This non-verbal communication can go a long way toward getting a feel for someone and being comfortable spending time with them. The idea of spending an afternoon with people you know a little should make you more excited than nervous.
I’m a big fan of casual dates before the romantic ones and recommend that first dates with these people be fun and light-hearted, providing plenty to talk about and do. Ideas include events like fairs and carnivals, fun places like amusement parks or the zoo, interesting spots such as museums or art galleries, and activities like bowling, mini golf, or a bike ride along the coast. What these ideas all have in common is that you’re able to talk and get to know each other, but the conversation doesn’t have to be driven by stories about yourselves, it can evolve from what is happening around you. Not only that, if things aren’t going well you can cut these dates short or simply muddle through while getting some enjoyment from the activity itself. One last piece of advice, stay away from the long dinners, instead opting for lunch or dessert and coffee.
People you don't Know at All
These are blind dates and the people you've exchanged emails with online. These first dates are the source of the great dating horror stories you will be laughing about with your friends for years to come. The guy who has 11 cats, all named after his World of Warcraft characters, the girl who keeps accusing you of flirting with the waitress, the guy who actually is flirting with the waitress and proves it by asking her out while you're still at the table, you know the type. These dates can be a nightmare and because of this you should make them flexible enough for a quick escape. The kind of flexibility I'm talking about is finishing your drink (or not), telling the person it was nice to meet them, maybe throwing out an excuse to be nice (optional), and being able to drive off within a few minutes. Good examples include happy hour, a cup of coffee, a hot dog or pretzel in the park, ice cream at the beach, maybe even things like pool, cribbage, pinball, or darts.
No matter what your gut says, don't plan a long dinner, don't commit to an activity after dinner, and never, ever schedule an entire afternoon. I beg you not to do it. If you don't know a person very well, meet them casually, have a nice conversation, get a feel for each other, and call them later for a real date when you hit it off. You'll demonstrate that you know how to ease into things, that your time is valuable, and you'll also save money on bad first dates, which you will then be able to squander on good second and third dates. Besides, if you really hit it off, you can always spend the rest of the evening together anyway.
Keep is easy. Keep it casual. Keep it cheap.