Arrive on time; this means 5-10 minutes early. If you are on time, consider yourself late. Why not a little earlier? Because she’s still getting ready… Life happens and if you are going to be late, let her know immediately and tell her why. And it better be good.
Attire: Dress for the setting, but dress up just a notch, and be careful about over doing it. You don’t want to out-dress her, woman tend to frown upon that. If you’re doing lunch or coffee, stay away from anything that you would wear at the gym or food shopping. It is casual, but remember: this is a date. Lean towards a shirt with a collar, and wear clean shoes. They pay attention to their shoes and might notice your dingy gym shoes. If you’re headed to dinner, wear a jacket. If you don’t have one, buy one. It’s amazing how much more dialed in you will look even if you’re wearing jeans and a t-shirt. First impressions count.
Cologne: one or two sprays. She should only smell it if she gets close to you, not from across the table.
Grooming: Manage that hair, and that doesn’t just mean the kind on your head. Get rid of the Ewok coming out of your ears and nose. And clean up the eyebrows. Again, women spend a lot of time on their small details so they will notice if you have made a similar effort. The details matter. Fingernails: clean and trimmed.
The setting: Find a place that is agreeable. Going to an Indian restaurant; does she even like Indian? Get a reservation, it shows you’re on top of things and have made an effort. Will you be able to hear one another? Bars are great for hanging out with the guys, but not for hearing what she has to say. That leads me to my next point.
Conversation: No woman has ever had a date and gone back to her girlfriends and said, “It was horrible, all I did was talk about myself.” Seriously, at least 60% of the conversation should be about her. Most women tend to communicate more than we do so let them. Keep it positive. The goal of a date is to get to know each other and to have a good time. If you start complaining about your job, congratulations, you have just exited the fun zone. Good luck getting a 1second date. Keep the conversation light. There’s no need to dig deep with the details. Just see if you guys get along and if there is a mutual attraction.
Picking her up: If you are, go to the door. Dropping her off, walk her to the door. Don’t be scared, be a man.
The kiss: Unless it is super obvious that this is going to happen (we’re talking about the first date) save it for another time. Wrap it up with a hug. If she really wanted one, you just had a great date and left her “wanting” a kiss from “you.” That is a good thing, not a mistake. And for the date when it is right, don’t wait until the end of the night when you drop her off. It’s too much pressure for both of you. Wait for a right time, like after the meal and you’re opening up a car door for her (do that as well gentlemen), or if you’re walking back to the car. She won’t expect it: score one for the spontaneous guy (that’s you Einstein).
Who pays?: You. If she objects, then gracefully stand down and allow her to do so (this is not the 1950’s, it’s okay). She likely has a reason, but don’t push for an explanation. Smile and say thank you.
How to handle silence: A moment of silence is fine, but of course can lead to discomfort. So, resort to your bank of talking point and questions. Oh, you don’t have one. Make one, preparation reduces anxiety.
Your phone: Leave it in your pocket or better yet, your car. By no means should it touch that table and don’t “check it.” If you’re waiting for an organ donor, you shouldn’t be on this date. She should be getting all of your attention, not 90% of it.
When to contact her again: Rules of dating say 2-3 days so you don’t look desperate. Screw the rules, show her that you’re interested, and since you broke the rules, she’ll notice… Wait a day, but don’t go overboard. Let her know you had a great time, then feel out the conversation and go from there. Don’t push for the next date… Be cool.
When the date goes bad: Don’t wait forever to wrap things up, but don’t be too abrupt. Most important, BE NICE. So what if this isn’t your soulmate, show her some respect and that karma thing will come back around.
Most important: Have fun and be nice!
-Ken Miller