He went for the kiss - got the cheek but that wasn't his only issue with this  girl.

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Hey Doc,

A little story from the field. I need your verification and coaching.

I’m 32 and I took a 22-year-old out (Red Flag). I am attracted to Riley’s beauty and youth. After a couple back and forth on the dating website, we had a good Starbucks date and I got her number at the end. I called her a week later and set up a date. She sounded happy to hear from me and gave me her address to pick her up. So far, so good.

On the dinner date, Riley talked about her exes and I gently tried to change the subject on multiple occasions. I kept thinking, “I don’t want to hear about all the dudes this girl has been through.” But she kept bringing it up, so I went along with it and figured I could at least learn why she got rid of them and verify “The System,” which it did.

After she spilled her guts, Riley expected me to do the same. I’m thinking, “I have to get off these negative subjects.” So I gave her a couple of jokes: “You’re my first date,” and “The girls I dated in the past weren’t as good as you...so far,” etc. Anyway, Riley kept after me, so I gave her a little more, but not much. Then she switched to “What do I want in a future relationship?” And I answered “A Flexible Giver.”

At one point, Riley asked how many times a boyfriend and girlfriend should hang out per week. I said two to three. Well, she ended the date right then and there. She said she wouldn’t bother dating a guy unless they hung out five times per week. Needy? Insecure? I couldn’t figure it out.

We got up and left and I knew I was most likely dead in the water due to a combination of not being able to get off the heavy subjects, her attitude, not understanding romantic love, and being in a rush to figure me out.

On the drive back to her place (she lives with her mom), she acted a little more playful so I thought maybe I wasn’t dead, so I went in for the kiss at the doorstep. She pulled her head to the side and I ended up kissing her cheek. Then she hugged me hard and pressed her cheek into my lips a bit, but it still felt like a rejection.

I thanked Riley for the fun time and walked back to my truck. As I was walking she called, “Don’t take yourself so seriously.”

Questions: what did she mean by that last comment? And should I call this girl again in five to nine days? I’ve been on a roll with like 20 different dates in the last couple of months and all have gone well, but this young hottie has me a bit confused.

Tiny - who is ready to move on if you give me the word

Hi Tiny,

Taking a 22-year-old out IS your first Red Flag! You at the age of 32 should be with someone 26 years old or older. Riley simply isn’t grown up yet. All men love youth and beauty — what men don’t?

But it’s really great that you tried to steer the talk away from negatives and past romances. For some reason, lots of women think that when they go out on a first date they’re supposed to talk about all their exes, as if being open about all the losers they were with will somehow endear them to the new guy, when the last thing in the world he wants to hear about is her former boyfriend.

What Riley gave you was what I call the HARD INTERVIEW. 

When Riley asked you how many times a boyfriend and girlfriend should see each other per week, you should just have said “Whatever the girl wants.” In other words, you should have just gone along with her.

But you learned that what you have here is a structured, hard-headed, Beautiful, spoiled 22-year-old.

And every young guy that she goes out with will be happy to answer all of her tough questions. But you, being a student of “The System,” know that it doesn’t help the relationship.

Riley isn’t needy or insecure. The point of dating is getting to know someone, and then figuring out down the road if you want see the other person five times a week.

Riley wants to get all of this done right away. What she’s trying to do is pin you down straight out of the chute. She might as well have mailed you a 10-question form and said “You better answer these questions right!” And then you could have skipped the first date and gone straight to the second if she liked what you marked on the form.

That said, I have to tell you that you really have “The System” down and you read the situation for what it was. Very impressive, Tiny. But again, a 32-year-old doesn’t go out with a 22-year-old. For as good and smart as you are, though, you blew it by going in for the kiss. You don’t kiss on the first date. You kiss on the second date. I can hardly believe you did this because everything else you did was just perfect, pal. You’re a sharp guy!

When Riley gave you her cheek, it was a rejection. Because you didn’t answer her little questionnaire, therefore it was time for you to be in pain. Like my cousin Fast Eddie Love from East L.A. says, “Isn’t romance lovely?”

When Riley told you not to take yourself so seriously, she was putting you down for something that SHE did! She’s the one who takes herself way too seriously. She’s the one conducting the hard interview.

Typical reaction from a STRUCTURED female – when she does something wrong, she ends up reversing it on you! You should have told HER to not take herself so seriously! Like my Uncle Jethro Love says, “The shoe should have been on the other foot!” That was a negative and a putdown, Tiny. Riley had to get a shot in on you because you didn’t beg her for five dates a week.

It’s a waste of time to call her again. She’s a spoiled princess. And because she’s young and Beautiful, guys will just fall at her feet. You’re not confused, dude. Your Interest Level is too high – that’s your problem.

Remember, guys: any girl who subjects you to a hard interview is out.

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