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Jolene (not her real name) and I recently broke up after two years. On the surface, this might not seem like a very interesting subject, but I’m confused about what’s going on. In order to properly understand my situation, I need to tell you about the unusual factors involved in our relationship.

Jolene is the sister of a very well-known celebrity actress, one who is often mentioned in “Top Women” lists. She has a very controlling mother and a best friend who is also her sister-in-law. All three of them now live in Los Angeles, having moved there from a smaller town in central California. (Read the article)

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Before we get into today’s article - I want to send a thanks out to Lost in Smallville blog. They were kind of enough to link to one of our many posts. They linked to Can You Spot the Man’s Head in 3 Seconds? Thanks again for the link.

I’ve been with Shana — a stewardess and a “9” — for six months. She has a lot of good qualities and values on top of her gorgeous looks. She’s kind, giving, and caring. I have done “tests” on her and she’s definitely not in love with my bank account (I’m quite well fixed through my various investments) and is certainly with me for who I am.

Shana was the one who first said the “L” word. I believe her Interest Level is around 95%, as she always talks about our future, how much she loves me, that she can’t wait to get married, and that she can’t wait to have kids with me. A few times she has also given me hints like “where’s my ring,” and on a daily basis she says “I love you” over 20 times, while I keep my responses to a third of that in order to stay a Challenge. (Read the article)

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I’m still learning “The System” and getting better at it with each girl. I just want to thank you for writing your book; it has helped me more than anything else I’ve tried with women and dating.

But here’s my problem. As hard as this is for me to admit, I’m a 27-year-old guy who’s never had a girlfriend!!! I can approach girls, get numbers, and even second dates thanks to your techniques, but that’s as far as it goes. The thing that trips me up now is when I’m dating a girl and she asks me, “So, how many girlfriends have you had?” And “What happened to your last relationship? Why did you break up?” (Read the article)

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First I’d like to say thank you for the help that you are giving to all of us guys who are having problems with the opposite sex.

Kareena is an Indian girl I work with very closely on my job. I make her laugh, and she touched me several times, but I didn’t know how to close because we are from different cultures. (I’m African-American, by the way.) I remember that you said to be careful when dating people from different cultures because lots of times the girl’s parents decide who they want their daughter to end up with.

Well, today I finally did close. I asked for Kareena’s home phone number and without hesitation she gave it to me. But as you say, just because you get a woman’s phone number doesn’t mean that she has high Interest Level. It could be that Kareena doesn’t know how to say “no,” and she was just trying to be nice to me because she has to work with me every day. (Read the article)

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I’m interested in Valerie, a very attractive young woman in my psychology class. I noticed her checking me out from the beginning, but I tried to remain a Challenge and waited until one day when after class she initiated a conversation with me. I kept it light and easy and teased her. The conversation kept going – I know, this was probably a mistake – and instead of asking for her home phone number, I said “Valerie, would you like to grab a cup of coffee with me?” She said “Right now?” and I answered yes, let’s go to the Starbucks right down the street.

So we went and drank coffee for 35 minutes. (I paid for the date, by the way.) During these 35 minutes she asked lots of personal questions, like what do you do, what are you studying in college, tell me about your family, etc. I saw all of these questions as buying signals. However, Valerie did not touch me once during this impromptu coffee date. (Read the article)

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What’s your opinion of “damaged goods?” I guess the smartest move is to never get involved in the first place, but what if you don’t know that going in?

I dated Samantha, a great girl with some heavy baggage, for just over a year. She’s had some terrible things happen to her, and some of them involved me. (I won’t go into specifics because I know that your column is G-rated.)

Anyway, she kept waffling on our relationship, wanting it but unable to fully commit to it. Each time that happened I pulled back and told her to give me a call when she figured herself out. After a few days she would. This back- and-forth went on for a while. She would get really into it, talk about marriage, wanting to have kids, and all that stuff. But I wanted the
relationship to prove stable before I moved into any of those areas. (Read the article)

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