He’s been going out with her for 5 months and hasn’t kissed her on the lips! Plus there is a huge age gap between them – this guy needs a lot of coaching – Find out what I mean in your free weekly article below plus visit our QUICK LINKS for FREE dating women advice:
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I have read your book again and again whenever I feel something is wrong with a girl I’m going out with. I just want to say that your book is GOLD! When I read your book, I realized that I had been living my life as a WIMP! A pushover and a stooge! But I’m doing my best to improve day by day.
So here’s my story. The woman’s name is Caroline – she’s hot, funny and she’s a little bit older than me. I’m 25 and she’s…38. She’s a single mom and has a kid. Anyway, we work at the same office but on different floors. I don’t know how I pulled it off, but I asked her out for ice cream and she agreed, and we have been going out on a weekly basis ever since.
As you said in your book, always keep things light and funny, always make her laugh, and no emotional garbage. But Caroline is the one to talk about her past, so I don’t know what else to do but listen. We have been going out for five months now, and her questions to me are getting more and more personal (awkward questions too) and she often asks me to tell her more about myself, but I feel like I’ve already told her everything. And she has compared me to her ex, which is weird.
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If I don’t ask her out, Caroline does the initiating. You said no group dates, but I screwed that one up. She asked me if she could bring her son along once and I said okay. Being with her son made me feel like I was “Dad” or something. It was kind of awkward.
After a date I always give Caroline a kiss on the cheek. I can’t bring myself to kiss her on the lips, but I think she’s fine with it. From what I can see, she is a Flexible Giver. She cooks for me once in a while. She has Integrity, but once a month she and her kid have to meet with the biological father, just so the kid can see his dad. She did say that she was only doing it for the kid and nothing more.
Am I on the right track with Caroline? Or am I not seeing something here? Doc, please give me an assessment. What more do I need to do? Do we just keep going out until something happens?
Truman – who still has lots to learn
Instead of picking up “The System” and reading it when you’re having trouble with a girl, you should read seven pages a night before you go to sleep. If you do that, you’ll end up reading the book once a month. Don’t go to it only when you have a problem – always be in the book and have the book inside your head.
On the other hand, look at how much you’ve learned so far. You’ve realized how you’ve been coming across to women, and you now see what changes need to made in order to improve. Most men don’t have the foresight and guts to do even that.
Dude, Caroline is NOT a “little” bit older than you. She’s a LOT older than you. If she were 28 I’d say she was a “little” older than you. She could and should be dating guys 45 to 50 years old. So why are you trying to change the reality of the numbers? In addition, she has 10 years lead time on you because romantic love is the woman’s turf. So in reality you’re going out with a 48-year-old — someone almost twice as old as you.
When Caroline talks about her past, ask her questions. Don’t just be a “yes man.” You have to show interest in her because she has the ability to hurt your heart. And if you feel like you’ve told her everything there is to know about your 25 years on earth, just repeat yourself. That’s all you have to do. Regarding her ex, all women COMPARE. But they hate to be compared to other females. Ironic, isn’t it?
You should have turned Caroline down when she wanted to include her son in your date. It was too soon to meet her kid. To you Psych majors, you should have at least six months in with a woman before you meet her children and you’re already mumbling about marriage or where your relationship might be going. But if you have to see her kid, just play “Uncle Truman.” You’re not his dad and you don’t have to be his dad.
But something else you have to realize is that when you get Caroline, you’re really getting TWO people – her and her kid. And when you’re 37, she’s going to be 50. She’ll not only be older, she’ll be a lot older looking than you. So that’s also going to be factor, as well as the fact that you’re going to be raising someone else’s kid. And what about if she want kids with you who will be half-siblings to her son? Is this what you really want, Truman?
Now let me get this straight. You’ve been going out with Caroline for five months and you haven’t kissed her on the lips yet? Doesn’t she ever ask you why? And she just goes along with this? Don’t you think it’s strange that you’ve been going with someone for 150 days and you’re afraid to kiss her on the mouth? Something’s not right here. It says in my book that on the second date you have to kiss the girl on the lips, and you’re not doing it. You say you read “The System” from time to time, but you don’t have it memorized, otherwise you wouldn’t be acting like this.
Of course Caroline’s only seeing her ex on account of her kid. She doesn’t dig her ex – she got rid of him. Have you ever asked why and what he did wrong?
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My friend, I think you’re getting in over your head with Caroline. You should be going out with women between the ages of 22 and 25. Like my cousin Rabbi Love says, “You’re a generation removed from this woman.” And given that age difference, maybe she doesn’t want any more kids and you’ll want your own.
What you need to do is memorize my book. You haven’t read it once a week for 15 weeks like you’re supposed to – if you had, you’d be kissing Caroline on the mouth. And I don’t like that she’s brought her kid around you. Like my cousin Fast Eddie Love from East L.A. says, “He’s going to get mixed up about who his old man is.”
On the surface it looks as if you and Caroline get along, but I see your age difference becoming a huge problem down the road.
Remember, guys: when you’re young, date women who are younger than you.
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