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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 Relationship Advice (8)


    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. 


    Is A Threesome A Good Idea?

    Lennie, my guy wants me to have a threesome. I'm scared it will ruin our relationship. I want to keep him happy, but I'm scared this will become a slippery slope of debauchery. Should I or shouldn't I? I like monogamy.

    Dear Monogamist, Your question is difficult to answer as there are many variables. I am a firm believer in keeping things spicy in the bedroom, and if adding a third party, or even a fourth party will do that, then why not. That said, it depends on the emotional security and self-esteem of the people involved. If you are easily jealous and will wonder if he's engaging in other extra-marital or extra-relationship activities, then a threesome is probably not for you. I think sex is sex and love is love, and that the two can be separate with a very secure couple. However, one often doesn't know how secure/insecure the other is until they test the strength of the relationship. Sometimes keeping someone on too tight a leash will lead to more temptation for the leashed person and ultimate betrayal. Sometimes the "idea" of a third party, and just flirting with the idea, is fantasy enough to ignite things in the bedroom. Clear as mud, right?



    Once A Cheater Always A Cheater?

    Dear Lennie, My ex and I are still pretty good friends. We have been friends for forever and dated for 3 years. He cheated on me, a lot, so obviously things didn't work out, but we still hang out from time to time. Anyway, every time he sees me he tries to get into my pants. Well, long story short we ended up sleeping together and a week later I found out he has been dating some chick for about 3 months and she just found out she is pregnant with his baby. I don't know what to do. Do I warn this chick? Or just let it go and cut all ties with him and those people?

    Dear Cheated, First, let me say "ouch" that's gotta sting double hard! I think you have learned your lesson and won't allow yourself to be used and hurt by a cheater like this again. As for the other woman, if you caution her you will just come across like the scorned ex-girlfriend and will likely create more drama for yourself. You don't owe her anything, and she will learn her lesson in due time. Just be thankful you are not in her position, cut all ties, take the high road and move on. 


    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.