Dating Women Advice: Was John Legend Ever Tempted To Go Back To An Old Girlfriend?

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He's CLUELESS with his ex and DISLOYAL to his girlfriend - other than that he's doing fine!


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Hey Doc,

I’ve been in a good relationship with Samantha for six years. As you can probably tell, I’m following your coaching closely, having kept the relationship for this long. But I have to add that we’re not married and have no kids. So maybe this says something about our relationship.

Recently things have gotten worse because Jill, who I dated before I got involved with Samantha, has come back to town and called me to come over to her new place and fix her window. I made polite excuses, and we decided to catch up later. All the feelings I had for Jill began to swirl back, to the point where I couldn’t contain myself and asked to meet with her. After the first call, I hinted that I was not available. But later I said that if I was not taken by Samantha I would have been over to fix her window – and more.

Because Jill had to move to a couple of different addresses before she found a permanent one, it took two months to arrange this meeting. When I did -- oh boy. We started to become very flirtatious with each other. Now Jill wants me to come to her housewarming party. I think she wants more than just that.

So my question is this: do I come clean flat out with Jill and tell her that I’m interested in her again, or just keep things as they are (which is nothing really, because it’s all only in my head up to this point). My inclination is to not succumb to my weakness for Jill. But I don’t know if I can.

I guess this has stirred up the doubts I’ve been having in my current relationship with Samantha.

Thanks in advance for your coaching, Doc.

Richard - who doesn’t want to come off looking like an idiot


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Hi Richard,

First of all, let me ask you this question: how do you go out with a girl for six years and not marry her? How does she go out with you and not tell you that unless you marry her within a certain amount of time, that she’s wasting hers? If you really dug Samantha, you would have married her after two or three years.

Now Jill is suddenly in the picture. Dude, you know what the rule is: YOU CAN’T GO BACK. You and Jill broke up a long time ago. She remembers everything that you did wrong. Since your letter doesn’t tell me anything to the contrary, I have to assume that she dropped you. Now she calls you out of the blue after six long years to come and fix something? She doesn’t ask how you are or whether you’re dating anyone? This babe knows she has you wrapped around her finger if she has the guts you to ask you to fix her window when she hasn’t seen you in six long years! She’s a USER. And she has ZERO Interest Level in you or she wouldn’t have dropped you in the first place.

There was no reason to catch up with Jill later. You should have caught up on the phone, given her 15 minutes and said “Good to talk to you but I have a girlfriend.”

Why did you ask to meet with her? Richard, she doesn’t want you. Like my Uncle Jethro Love says. “All she wants is a carpenter.” What she cares about is getting her window fixed. Instead of conning you to come over, she was brazen enough to come right out and tell you she wanted work done. She knows that your Interest Level is through the roof and that she can just call up out of the blue and you’re going to run to her with your tools and fix her window. That proves to me that she’s a USER, like I said before. She has no respect for you. Like my cousin Fast Eddie Love from East L.A. says, “She knows you’re a stooge.”

And why are you talking about your woman to another woman? Now I know for sure you haven’t actually memorized my book because it states that you never do that.

Why is Jill moving around to different apartments? You find an apartment and you rent it. Don’t you smell a rat here, pal? Like my cousin Rabbi Love says, “This woman doesn’t make any sense.” You’d better stick with Samantha, because Jill is a goofball!

Now Jill wants you to come to her housewarming. Why? Does she need a bartender too? She doesn’t want more of anything from you, Richard. She dropped you, you were history, and she’s just going over old times, and now you’re blowing it all out of proportion. Your interest was over 90% and it still is. And by the way, this proves that she dropped you.

Of course you don’t come out and tell Jill that you’re interested in her – because she’s not interested in you! Remember, she wants a carpenter and bartender, not you as a boyfriend. She’s looking for free labor, that’s all. It’s obvious that this is all only in your head because Jill has no interest in you. She never would have broken up with you if she was interested. She’s just going to use you to get her apartment fixed up and then dump you again.

Don’t have any illusions that you’re going to replace Samantha with Jill. And I don’t like the fact that you’re being disloyal to Samantha. "The System” says that we DON’T USE WOMEN. And while you’re going with Samantha and flirting with Jill, you’re doing just that.

It sounds to me like you don’t know what you want, guy. Why does it take an old flame showing up for you to realize that you now have a bad relationship when for six years your relationship with Samantha has been fine? You’re fickle, Richard! You better figure yourself out!

Remember, guys: unless you memorize "The System” you’ll be clueless with women.

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Leave a Reply 4 comments

Russ - 17 October 2015 Reply

I’ve been in this same situation where I was in a long term relationship but wasn’t 100 percent in love with the girl. I broke up with her and it was hard because I really liked her. I think I was afraid of being single and lonely. But that was better than wasting her time.

I think Richard should break up with Samantha and also forget about Jill. Doc’s right, the things Richard did to lower Jill’s interest level will never be erased from her memory. He should become single and try things like and see if he can find a girl he’s as attracted to as Jill.

Love the weekly articles Doc.

    DocLove - 17 October 2015 Reply

    Thanks for your support Russ!

Norman - 20 October 2015 Reply

Hi Doc

I went out 10 years ago with Caprice who is now married (before I had the system) after date 1 told me (womanese) “we have different outlooks//values.” Two weeks ago Lisa a mutual friend of ours called me that Caprice has a girlfriend Molly who she wants to set me up with. Caprice now wants to act as a Matchmaker. I told Lisa I find my own dates and I am seeing someone just to get Lisa off my back . Doc, Lisa keeps on calling me up wanting me to meet Molly. Do you have any suggestions to tell Lisa to stop harassing ? Just wondering why is Caprice playing matchmaker, when she thought 10 years ago we had different outlooks/values? Also, after a date when I am not interested in meeting a woman again. How long should I wait to call her? (The system says 7-9 day to see her interest level) My questions is even for a woman I am dumping?

    DocLove - 21 October 2015 Reply

    On the woman harassing you to meet her friend just say “I’m dating someone now and not interested in meeting anyone new.”

    As far as when you’re dropping a woman if it’s 1-3 dates in just don’t call her again as there is not much invested from either side – from date 4 on you have to be polite and tell her you’re not interested but don’t be cruel – just say an old girlfriend came back into your life. You don’t have to wait 5-9 days either because that rule is only to build INTEREST LEVEL but if you are never going to see her again it doesn’t matter

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