
1) Plan and evening or weekend
You’re trying too hard if the evening you’ve arranged required more than two reservations. You’re not trying hard enough if you show up expecting her to improvise a game plan.
Some men make the mistake of going all out on the first date—the limo, the four-star restaurant, the front-row seats. This worked for Frank Sinatra, but unless you once sold out the Copa Room at the Sands, it will not work for you.
If such luxury is not your standard, you’re going to be out of your element at a time when you should be smack in its middle. Stick with what you know. Take her to a place you like, where the owner and host and waitstaff know you. Familiarity and friendliness impress us, unless it’s a topless bar.
And don’t forget: Clean your car. If you invite her back to your place at the end of the evening and your home is a little messy, that’s not such a big deal. (You might even get bonus points because it will appear that your proposition wasn’t premeditated.) A messy car, however, is a different story. Something about it just says, “I want to be alone. Forever.”
2) Mind your manners
Think boyfriend, not butler.
Men with good manners are cute and can even be sexy. Men with excessively good manners are obsequious and often repulsive. It’s a question of degree: If it’s raining or she’s wearing a formal gown, go ahead and open her car door first; otherwise, it’s fine, after the first few dates, to just unlock it from inside. Getting her a drink from the bar is great, but don’t order dinner for her. Opening doors is nice, but not if you have to sprint ahead of her to do so. Leaving her at the coffeeshop while you run to the deli for the soy milk she likes or mailing a shower puff to her at the office because she mentioned in passing that she needs a new one (true stories) is way too attentive.
Relax. We’re not expecting too much. Show us just a degree more courtesy than you’d show the next guy, and you’ll impress.
3)Take a Fun Trip
Go the fun (not romantic with a capital R) route for a first-time getaway.
Flying to Paris with a man sounds romantic to a woman. Your mentioning it on date three sounds moderately psycho—and a lot like a false promise. When you first knock suitcases with a new lover, make sure they’re weekender bags—and drive to a nearby casual destination. Heading to Texas for your cousin’s wedding: not so casual.
Side note: If you’re both outdoorsy and athletic, an adventurous weekend spent rafting or rock climbing will show off your muscles and be sure to impress. However, if you lack athletic grace, it’s a bad idea to ask a woman you’ve just started seeing to go on, say, a ski weekend. Your sitzmark won’t be sexy. Her fake fall to ease your embarrassment won’t be subtle. Everyone will end up bruised and turned off.