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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.

    Please check out my Sex and the City style novel Blow Me—available now in e-book and paperback on my website and lulu.com. Also available in ebook on amazon.com and Google books.


    Entries in Advice for Women (27)


    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:


    Dating at 40

    Lennie, I'm a woman in my early 40s and I haven't had a date in two and a half years. I don't even know where to start. Help.

    Dear Two and a Half:  The older we get, the tougher it is to date for many reasons. We become more particular about what we are looking for, we have precious little free time to date, and we've had so many disappointments that we are easily discouraged and often skeptical from the onset. The most important thing is to stay positive, keep looking beautiful, and try to remain playful. Often when women get older, we know so definitively what we want that we forget that in order to get what we want we need to be coy. Particularly our generation, because we were told we could be "equal" and so we had to toughen up a bit so we could compete in a "man's world" so to speak...some men are threatened by that...so play more helpless even if you aren't. Men want to feel needed and useful. Online dating plays an important part in today's dating world, but much time is wasted communicating back and forth. If you are going to online date, try to set up a phone call and a date as quickly as possible. The best way to meet people is to get out in the world an stay off the web. Get out there and live your life and don't be afraid to approach men either. 


    Feeling Left Out

    Dear Lennie, I've been dating a guy for four months, after being just friends for two years, and things have become serious (and wonderful!) quickly. I have young kids and he has adult kids from previous marriages. Although he's become close to my kids and they are building a great relationship, I have yet to meet his (adult) kids. When one of his daughters graduated from college recently, I was not invited because "it would have been awkward" for his kids and ex-wife. I've been having my own pity party ever since and am feeling not only left out, but also wondering if he really means it when he says he loves me. What's your take on his avoidance of introducing me to his kids and should I bring it up with him or just stop being a big baby about it?

    Dear Left Out, I do not feel that his not introducing you to his children is a reflection of not loving you. I'm sure he's just looking for the right time and place. Even though you introduced him to your children, he may have other concerns. Little kids are a lot less judgmental about newcomers than adult children. And, it's also harder for a mother of young children to avoid introducing children to a man she's dating, because of bed times, sitters, etc... it's just bound to happen that your children would be introduced first. Inviting you to a college graduation would not be the appropriate time to introduce you, and I'm sure he probably felt that he was doing you a favor by not introducing you during a personal event like that. Graduations tend to be for family and close relatives, not for new girlfriends who have not met the children. I would think that would be an "awkward" event for you to attend, having never met any of them before. He may have had issues introducing his children to previous girlfriends and may be sparing both you and him from a lot of grief by waiting until he feels that he's ready to make a lifetime commitment to you. Further, by involving the children, he will effectively involve the ex-wife and he may be trying to avoid some drama there. My feeling is that everything is good, that there is no reason for concern, and he's just going at his pace... enjoying the honeymoon period for a while before introducing the complications of his family. I would say end the pity-party, relax and don't pressure him to meet his children. It will happen when he's ready. 

    I hope you find this advice helpful.  Good luck, deep breaths... just let it happen and don't worry about the future. Enjoy the moment. That's likely all he's trying to do :)


    I'm hooked on a feeling

    Dear lennie, I've been dating this guy for almost a year and he controls me. I'm hooked on a feeling that he's cheating on me. He talks to all these girls. He said he isn't cheating on me and says he cares about me and I'm in his heart...I really love him but I don't want to get hurt...what should I do?

    Dear Hooked On A Feeling,

    First off, a man should never control a woman. There is a saying, "if you love someone set them free, if they come back to you they're yours." While I don't know specifically in what way he controls you, a man should never make a woman feel like she has a muzzle or leash on her. Love is not about control, it's about freedom. I would say trust your instinct when it comes to cheating and betrayal. While he may not be cheating, if you are feeling controlled and you are that concerned about his behavior towards other women, then this does not sound like the right relationship for you. Find a less controlling man who you can trust, that way you'll protect yourself from getting hurt. With this guy you're currently seeing, it sounds like you are already hurt.



    What To Wear?

    What do I wear on a first date with someone I met online? If we are just getting drinks/coffee, I don’t want to look like I’m trying to hard but at the same time, I want to look good. Any tips?

    Whether you met online or not, you should wear something attractive, well put together, and a little conservative on a first date. If it's coffee, I would not show up in your workout clothes. Wear a nice pair of jeans with a cute top. Nothing revealing. If it's drinks, the same attire will work. You should put in a little effort to show that you care about your looks, but don't go over the top with makeup or wear something too provocative. That will just send the wrong signals. If he likes you when you are looking simple and natural, he will love the glammed up, sex-kitten version too. Make sure he's worth the effort and someone you want to take to that more flirtatious level before sharing that side of your personality and sexuality.