MillionaireMatch.com - the best dating site for sexy, successful singles!
MillionaireMatch.com - the best dating site for sexy, successful singles!

Lennie's bookshelf: read

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

More of Lennie's books »
Book recommendations, book reviews, quotes, book clubs, book trivia, book lists
Search Lennie's Site
Follow Lennie

Now Available!
For International sales or larger orders, please contact sales@lennieross.com
Contact Lennie
This form does not yet contain any fields.
    « What is up with today's women? | Main | The next step »

    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. 

    Reader Comments (2)

    You are so right, Lennie. I find myself being judgmental and negative before I even go out the door. Attitude is everything. I think I need to be more playful.

    July 10, 2011 | Unregistered CommenterAnne

    I agree with Lennie. I am 39. I met the boyfriend with whom I live 20 days a month, 10 in LA and every few months 2 weeks in NYC, 11 months ago this week. (I was dating an older man in NYC but that ended about 6 or 8 weeks later).

    I absolutely agree with Lennie's assessment of the threat a very bright , articulate, educated woman will pose to a man, whether she has a career and/or money to match the degres or not.

    But you don't want to play dumb either.My mother is a high -profile lawyer in LA and she went to Hollywood High in the 50s. What she said to me about the "rules" back then still apply: You do not want to seem like a dummy or a ditz but you also don't want to come off like Madame Curie UNLESS you have met the guy online and right off the bat discerned a truly superior intellect with or without intellectual accomplishment, i.e. degrees , grad etc..

    If you meet a guy at a bar or a business function and you have gotten the early what do you do stuff out of the way and know this is a really intellectual guy, then it's okay to come off like brainiac/superwoman. But if the guy is just nice, and interesting and does not volunteer information which indicates a desire to talk about ideas or deep things keep it light.

    The only thing with which I partly disagree is the injunction of Lennie's to meet on the phone or in person and get offline. If time is an issue that's fine. But I met the boyfriend before this out of the blue on FB when I first got it and he found me through some college search and saw I like philosophy and lit. We emailed a month He was in NY and my college reunion was in about 2 months. When I saw him first time, we were already good friends, ton of phone. In a long distance thing rules are different on all levels but first and foremost you can't be with a monosyllabic guy. You have to be able to spend an hour on the phone gabbing if you don't see each other for weeks or even months.

    And my boyfriend a year older says that the intent focus of some women to get married is a huge turn-off.

    Playfulness and a sort of casual (not necessarily in a sexual sense) attitude is much better than the urgency to commit attitude

    July 10, 2011 | Unregistered Commentervictoria ordin

    PostPost a New Comment

    Enter your information below to add a new comment.

    My response is on my own website »
    Author Email (optional):
    Author URL (optional):
    Some HTML allowed: <a href="" title=""> <abbr title=""> <acronym title=""> <b> <blockquote cite=""> <code> <em> <i> <strike> <strong>