As in conversation and texting, one of the most common mistakes guys make when it comes to dating is that they try too hard to impress the woman and win her over. They believe that some specific activity or activities will cause her to like him more, when in fact the only thing that matters when determining whether a date was “good” or not is the level of connection you shared.
The goal of those first several dates shouldn’t be to get her to like you. Rather, your goal should be to see how much chemistry the two of you have, both physically and personality-wise. One of the biggest results of this mind-shift is not blaming dates that don’t end “well” on yourself. If you have a bad date, it’s probably because the chemistry just wasn’t there. If most of your dates are dry and boring, on the other hand, then this chapter was written for you.
My first date is almost always drinks or coffee for a very simple reason: we barely know each other. I enjoy doing fun things. I like planning new experiences and outside-the-box activities. That being said, if I take the time and effort to coordinate some activity and then it turns out I don’t even get along with that person in the first place, then I don’t even get to enjoy the activity I was looking forward to and wish I didn’t spend all of that time, effort and sometimes money to plan it. Drinks or coffee provide an easy way to find out if you both want to invest more time into seeing each other. If the spark isn’t there, you haven’t lost any more than a half hour and a couple drinks. If it is, well then we can look forward to something more elaborate for the second date.
The exceptions to this “rule” are either when we’ve previously discussed some specific activity for our first date or I’ve already had enough time to get to know her that I’m confident we’ll have good chemistry. In those cases, I just skip ahead to what I normally do for date number two.
Once you know that you enjoy each other’s company, it’s time to have some fun. Take a moment to think about all the activities you love to do or have wanted to do — whether it be shows, classes, playing pool, specific restaurants, art exhibits — but that you want to share with someone else rather than do alone. The more fun you’re having because you’re doing something you enjoy, the more she’ll enjoy herself. The more you’re worried about doing something she’ll like to get a desired outcome, the more she’ll feel your anxiety and agenda and not want to see you again. Check out the local events newspaper or website that every town has and pick out the activities that sound most fun to you. These second and beyond dates are the perfect for that. Cooking some delicious dinner is also a great date, but I’d save it for at least the third date if you haven’t been to each other’s places yet. If you can’t find anything specific that really tickles your fancy, bowling, mini golf, and ice skating are all excellent recommendations.
Now that you’ve got a few ideas for activities, this should be part of the logistics you’re taking care of. Instead of a general location for the bar or coffee shop, you can ask how she enjoys a specific activity: “Are you a burlesque fan?” or “Can you ice skate?” As long as she seems enthusiastic about an idea you suggest, you’ve just taken care of an important logistic for the second or beyond date. If she’s not a fan of your suggestion, then see what she has in mind.
As far as your behavior on the date, I remind you that it’s not about trying to win her over. She’s on a date with you, she already likes you. On the date you should be employing the same conversational skills that we covered in Section Two, and enjoying sexual feelings when they arise. The main difference between this conversation and when you first met is when it’s your turn to push the conversation forward, you should be past the boring interview questions and be much more curious about what she’s into, what turns her on, and what her plans for the future are.
As I’ve also discussed, every woman has different physical and emotional boundaries, and will open only so far on a first, second, or twentieth date. Some individuals need years of counseling before they’re ready to be physically and/or emotionally intimate with someone else, and no amount of charm will change that. Other individuals want to get much closer much faster, and they’ll be turned off if you hold back and treat them like a porcelain doll. Of course if she wants to go faster than you’re comfortable going, then she’s probably not the woman for you.
The best advice I can give for any date is to give the other person the benefit of the doubt that there’s something incredibly awesome about them that will fascinate you and look to find it. Be sure to have your own standards and watch out for any red flags that could point to deal-breakers, of course, but mainly just see if you enjoy this person’s company. Just like when it comes to talking to women in the first place, if you’re not having fun, you’re not doing it right.