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I’m 38 and dating two girls. Sheila is 22, goes to school and seems to have her life in order. She’s really sweet, very cute and I’m flattered that she’s so interested in me. I dated her for two months. We broke up because she wanted space and probably wanted to date another guy. So I gave Sheila her space, but now she wants me back.
The next day I met Morgan. She’s a 38-year-old, super-hot, long-legged blonde. I never had much in common with girls my own age, but I had everything in common with Morgan. She has her own business, is a single mom, and is very romantic with me. I had a great time just hanging out with her. She has a cool pad and car and everything! Her teenage daughter is cool too. When I started hanging at her house, I saw that she has over 30 guys in her phone. It’s her work phone, granted, but it bothered me. I dated Morgan for a month (27 days in a row). At first she said she wanted me as a toy. When I told her I wanted more, she started being all domestic and sweet. I really wanted to get involved with her, but I kept thinking, what if Sheila comes back? Morgan knew that Sheila was texting me, but didn’t say anything except for “Why doesn’t Sheila know about me?” I told Morgan that Sheila was just a friend.
After I introduced her to my mom, Morgan thought we were exclusive. We had a date that night but Sheila called and wanted to see me. I made up an excuse (that a friend needed my help) and cancelled with Morgan. I got together with Sheila that night, and Morgan suspected something, got upset and blew up my phone with text messages.
The next day Morgan said my cancellation one hour before we were supposed to get together was disrespectful and she doesn’t want to be disrespected. I told her that she was smothering me and had no right to get mad at me for canceling a date. I told her we shouldn’t see each other anymore, but she asked me to give it a couple days because she really enjoyed what we had and didn’t want to say goodbye.
Now I REALLY like Morgan, but the way I see it, she likes to be in control, any guy could have her, and she could dump me fast. Sheila is 22 and I have her practically trained.
Doc, which one would you go for? Thanks for your coaching.
Rex - who’s between a rock and a hard place
Hi Rex,
You and Shelia didn’t break up. She dropped you because she wanted SPACE. And she wanted space because you were all over her. To you Psych majors, when you press a woman, she wants space. When you back off from a woman, she chases you. Sheila probably didn’t even want to date another guy. The other dude probably had nothing on you whatsoever. It’s a rationalization on your part that you think she suddenly had another guy and had to drop you. Rex, she wouldn’t want to be with another guy if you didn’t keep pushing on her. That said, now that she wants you back, you can’t take her back. You get one shot per girl per lifetime. That’s it. So Sheila’s out. Next.
Why does it bother you that Morgan has 30 guys in her phone list? You don’t know who these guys are. If she’s a beautiful woman, she should have 30 guys chasing after her. Like my cousin Fast Eddie Love from East L.A. says, “It she’s that hot, she should have a hundred and thirty guys on her tail.” And she probably could if she wanted them – it’s no big deal. The point is that you can’t let it bother you. Like my cousin Sal “The Fish” Love says, “What are you, insecure or something?” Rex, you have to invest in “The System” and learn how to build up your self-confidence and not worry about the competition. Because like my cousin Rabbi Love says, “The only competition you have is you.”
Now let me be sure I have this right. You dated a woman 27 DAYS IN A ROW? Now I know for sure you don’t have my program! And now I can also understand why Sheila dropped you – she couldn’t breathe. It’s all as clear as a blue California sky.
But 27 days in a row wasn’t enough. You told Morgan you wanted more. Rex, you never tell a woman you want more – EVER. It’s the antithesis of Challenge to tell a woman you want more of her attention. If you knew what you were doing, she should be telling you she wants more. And when she said she wanted you to be a toy, you should have said “Honey, I’ll be an ice cream truck for you if you want!”
Now let me get another thing straight. You’re telling me you want to get involved with Morgan...but you’re worried that Sheila might come back. You mean you’re worried about the girl that dropped you coming back? The only thing that you should be worried about is being weak and going back to Sheila and letting her dump you again. You’re fretting about the wrong thing, buddy!
You told Morgan that Sheila was just a friend? Now you’re lying, Rex. I don’t condone lying to women. You keep your mouth shut with women, but you don’t lie to them. And by the way, how did Morgan know that Sheila was texting you? You should have kept your cell phone in your pocket instead of playing with it all the time and letting her see what was going on. Morgan knows way too much about the other woman. Like my cousin General Love says, “Man, oh man, you’d make a lousy secret agent!”
So you dig two girls and you’re already bringing one home to your mom? You don’t bring a girl home to your mother until you get at least six months in with her and she’s crying marriage! That’s when you should bring Morgan home – not now! Boy, do you have a lot to learn, Rex.
You lied again to Morgan when you said you were helping a friend. Know what your problem is, Rex? You’re a liar.
It’s nice that Morgan doesn’t want to be disrespected. But it’s funny how when you break a date with a babe she goes ballistic, but for all the dates guys never break, you don’t hear a thing. Amazing. But Rex, if you told Morgan she was smothering you and had no right to tell you what to do, you must be a very handsome fellow to get away with it, that’s all I have to say.
You have Sheila practically trained? How can you have a girl trained who dropped you? Girls that are trained don’t drop you, I hate to have to tell you that.
Which girl would I go for? Heck, I don’t know why either of these girls would have you! Because you’re a liar -- and I don’t like liars. Neither do clinically sane women.