Hey Doc,

I’m 22 and I’ve been taking Lola, who is 18, out on dates. I met her at a football game and asked for her number. She responded with, “Definitely, we should hang out some time!” I felt her high Interest Level. I waited five days before calling, and asked her out for a specific day and time.

We had a blast dancing and she was doing most of the talking. I waited another six days before asking her out for the second date the next week. On this date she was still doing 80% of the talking and asking lots of questions, to which I responded with short answers and joked and then asked her other questions, trying to keep her talking most of the time. On the third date, she was laughing, talking, and now also touching my arm (which she hadn’t done on previous dates). I dropped her off but didn’t go for the kiss. Maybe I chickened out. Should I have gone for the kiss on the second date?

In “The System” you talk about waiting longer if you know she wants to be kissed to increase the anticipation. I can tell Lola is interested, but I’m not sure when to go for the kiss. I can’t tell if she’s dropping hints to kiss her (she wasn’t looking at my lips or anything like that), or if I should even be anticipating her dropping hints. However, I’ve noticed that by following your book, a lot of girls will drop hints and try to hold my hand when they wanted to be kissed.

Anyway, I just completed a fourth date with Lola and her Interest Level was still pretty strong. However, I realized I was telling her more about myself than normal (probably due to my high Interest Level -- shame on me!). What I should have done was joke it off and ask her more questions about herself. I’m not sure if I’m out of the game because I haven’t gone for the kiss by now or if I lowered her interest by telling her a lot about myself.

How long should I wait before telling her more about myself? Is there a general rule for when I’m allowed to tell her more? Or should I just constantly try to have her do the talking? I know that having her ask me questions is a sign of her interest, but I’m not sure if I should ALWAYS be mysterious or is there a time when it’s okay to open up a little? Also, is it worth asking Lola out again if I haven’t gone for the kiss by now?

Ryu - who keeps trying to follow your rules

Hi Ryu,

First of all, let me say that you’re a very smart guy to follow my principles. But when Lola told you she would like to hang out with you, you should have said to her, “We’re not going to hang out – when we go out, I’m going to take you on a date!”

It’s fantastic that you waited five whole days to call this girl. Most of the guys out there call within two days. They don’t have the patience that you have. They’d rather go right out and destroy Challenge!

Likewise, it’s perfect that you kept Lola talking. Most men want to ramble on or brag and thereby turn the girl off. But in the first few dates, it’s best to let her do 60% to 70% of the talking, because you want to last. And of course it’s good that you recognized the importance of touching. For the most part, you’re doing great, Ryu!

But it was a mistake that you didn’t go for the kiss after the second date. Like my Uncle Jethro Love says, “You did chicken out, boy.” You should have definitely gone for the kiss, because if she turned her head and you got her ear instead of her lips, you could have thrown her number away and not wasted a moment more of your time. On the other hand, if she had asked you for a kiss or said, “Hey, when are you going to kiss me,” you could have said “I’m a very shy guy,” and flashed her a big grin. And that would have ramped up the anticipation. But the most important thing to remember is that you go for the kiss on the second date.

When you say Lola wasn’t looking at your lips, you’re off...

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