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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 Sex (3)


    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?



    Relationship Status: It's Complicated

    Dear Lennie: I made friends with an older man (I'm 30, he's 45) who recently ended an 8 yr relationship. He flirts, sexts, and emails daily, but doesn't want to do anything physical. We have an amazing connection and spend lots of time together, but he says he's not ready for a relationship. I don't want to give up on having him in my life, but he is in my heart and mind and taking up lots of my energy. Should I stay friends until he is ready for more?

    Dear Complicated, when a 45 year old man gets out of an 8-year relationship, he generally wants to be on his own for a while (read 2-3 years). Recently single, older men like to play the field and while he may flirt and show interest in you, he clearly does not want to play you, which means he respects you (a good thing). Don't give him a reason not to respect you by making yourself so available. At his age he may not want to have children or get married and he may look at a 30-year-old woman as someone who wants a family, so he could be protecting himself and protecting you from getting hurt. You may wait a very long time for him to be ready for a relationship, and there are no guarantees he'll choose you. I say be friends, but go on dates with other men and play the field yourself. If it happens with him, hooray! But, even if it does, I'd be very aware of addressing the age difference and desires to have/not have a family, marriage, etc early on so that you don't get your heart broken. Don't forget to think about the age difference later on, when you're 45 and he's 60.


    More Sex, Please

    Lennie, my boyfriend was on anti-anxiety/anti-depressant meds and never wanted to have sex. Now, he's off them and is always tired and still never wants sex. What can I do? I am starved for sex.

    Dear Sex-Starved, anti-depressant/anti-anxiety meds can repress one's libido. But, not taking them can cause a similar reaction. It's a double-edged sword. it's not so much what you can do, but what he can do. I am not a doctor or licensed therapist, so he should definitely consult his physicians about one idea that might help: working out regularly. Increasing his endorphins will elevate his mood and provide him with more energy. Hopefully, this boost in energy will manifest itself in a desire for more sex. The key to this solution is regular/daily workouts to keep those endorphins charged. Check out WebMD for more information on endorphins and exercise.