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Choosing Civility: The Twenty-five Rules of Considerate Conduct Blow Me Blow Me Half Broke Horses The Glass Castle Steve Jobs

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    If you have a question about dating, please email me through the form on this website (you may do so anonymously) or contact me by direct message on Facebook and I will do my best to answer your question. Responses are posted every Sunday morning.

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    Entries in Advice for Men (12)


    Why Did You Get A Divorce?

    Lennie, I'm a divorced, single dad with greatest son in the world. I'm always asked by dates "Why did you get a divorce?" I don't feel discussing my ex would be in the best interest of my son. I try to answer honestly and tactfully: Divorce was not my idea; I never cheated / lied / ran-off with cheerleaders, etc.; further, my son knows he has two parents who love him more than anything. Dates consistently dig for more. They want a reality-TV back story. I don't badmouth, instead I say we had different values and steer the coversation to my values. I would not probe them about their old boyfriends, yet my answer is not enough for them. 

    Dear Divorced Dad,

    If a woman is looking for the drama version, she is probably accustomed to drama. Your answer to the probing is clear, concise, and respectable. It can be a threat to some women if you have a flawless relationship with your ex, but that doesn't seem to be the case, it seems more like a mutual respect for the sake of the child. Very mature. Talking about the "ex" is an easy topic (yet not graceful) when trying to get to know someone, so makes sense it would be asked often. I think your high road approach and decision to be a bit private is wise. It could be these women lack trust and lack experience with relationships that ended on good terms. Perhaps these women need to grow up a little before they are ready for a solid man like yourself.


    Gun Shy

    Dear Lennie, I am in immensely in love with a woman who builds walls around herself. She dumped me 3 months ago due to external commitments, but I still love her. I really think it was that I didn't make enough money, even though I make $.25M a year.  Little by little and by charm and caring we are now seeing each other. We went out on a date last week and had a really great time again. We are now emailing every day and talking every day. She ended a letter to me by saying "I love you". As a guy do I let this go and play cool, or do I tell her I love her all over again. I do love her but I want to keep a little distance before we go any further again. A little gun shy now!

    Dear Gun Shy, its never fun to open your heart and risk getting hurt. Especially a second time! Tell her that you love her, but that you also feel vulnerable and don't want to get hurt again. Take things slow. She will appreciate the honesty, and the vulnerability, and this way you are letting her know that you don't want any more games. Protect your heart, but allow yourself to feel. By the tone of your email you sound like a great guy. It is understandable that women often worry about money, but you do well for yourself. She needs to think about what is important to her. Hopefully she is not a "material girl" who cannot appreciate that there are more important things in life (namely the love and respect of a great man) than Louis Vuitton. 


    Why Can't She Just Be Honest?

    Why is it that women drag out relationships? Why is it that women can’t be honest and just say that they do not like the person? At the same time, why do women expect the opposite from men? DJ

    DJ, great question. Women are only doing themselves a disservice in not being honest. Unfortunately, women are often taught to be polite and women are also conditioned to be afraid of confrontation. These two characteristics combined often result in a woman who does not speak her mind. That's often why women stay in the wrong relationship. They may stay because they have low self-esteem, and either don't think they can find better even though what they are in doesn't work, or they are afraid to be on their own. They also might think they can change the other person, which is a recipe for disaster. It is unfair that  women want honesty, and often can't be honest themselves. I do agree with you that it should be a two-way street with honesty.


    Looks aren't everything, or are they?

    I have been hanging out with a really great girl who I would like to be just friends with, but its tough since we keep talking. Also talking to my ex who is visually everything I'm looking for. She is funny but really insecure and jealous. She also has nothing going on in her life, no hobbies or anything, so I find that there isn't a lot to talk about with her. All she really wants to do is shopping, gym. Although she is an amazing cook. The other girl is beautiful, with a ton of energy. She is very dynamic but in my opinion she is too popular. I say popular in a sense that she always has men after her and seems to slightly lead them on. Now I get to the shallow part. I know my ex will always look the way I want her to. The other, although she is fit now I know it wont stay like that very long. It probably shouldn't matter but to me it does. When it comes down to it I'm actually really thinking about the visual part more than anything and that seems horrible. What are your thoughts on this? I know, I'm being shallow.

    Dear Shallow, we all know men are very visual creatures, but there are no guarantees anyone will stay the same....even you. Relationships should be founded on similar interests and values—not on how someone looks. Ultimately, you're going to do what you are going to do. Just don't go judging women who evaluate a man based on his finances when you are evaluating women based on their looks—double-standards—all the best with your decision.



    What is up with today's women? 

    Dear Lennie: My last relationship lasted 20 years. I'm now mid-40s and dating. Things are a lot different now then they were when i was young. Maybe it's the age of the women I'm dealing with, 35 to 45 years old. It seems they all have some kind of hatred towards men. Like everyone of then have been hurt and need to get revenge. Thoughts? T

    Dear T

    I hear this very often, and I think it relates directly to last week's post on dating at 40. I think women get so frustrated: they are exhausted by the fact that they have worked so hard on their careers, and perhaps didn't make time for a relationship, and those relationships they had didn't turn out so well. The pressures on women these days are intense, and I think sometimes they forget to stop and relax and just be women. We have the pressure of biological clocks, and not just in regard to babies, but I've heard of men looking at women in their 40s as only having a few good years left before they hit menopause. So panic sets in for women, and they are so busy rushing to the finish line of "finding Mr. Right" that they forget to stop and relax and enjoy the process.  It's also true that a lot of men treat women poorly (and the women allow themselves to be treated poorly, because somehow they grew up with low self esteem—been there myself). Many women in their late 30's early 40's feel like it's hopeless. It is important as a man to respect a woman's intentions—that is, if she is looking for a commitment, children, marriage, etc—not to waste her time. But, it's also important for women to lighten up in the process. I hope that makes some sense ;) My friend Hot Alpha Female has an interesting video blog on this subject: