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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 Breaking Up (2)

    Sunday
    Apr012012

    Break Up Phobia

    Dear Lennie

    I am a 40 yr. old man who has lost considerable weight and is entering the dating world. My slim looks are drawing the attention of many women and I am reading your articles and others to best handle the challenges of courting and dating a woman. My problem is that I don't know how selective to be at this stage of my dating career. I have limited experience and have had only one LTR. My fear is not at being turned down by them, but of the fact I will be breaking up with them if I don't ask the right one out. So basically, I fear the idea of breaking-up with women, so I don't ask them out unless I feel there is a really good chance things will work. As you can imagine I talk myself out of approaching many women! How selective should I be when deciding to ask a woman out?

    Dear Mr. Break Up: 

    Being selective is very important if your purpose is to find a life partner or long term relationship. And, I'm sure you will find that despite your favorable looks, women will often decline the offer of a date. So, I say, if you see a captivating woman, there is no harm in asking her out. Just be prepared that she may say no. That said, if you do get a date, listen to your gut and take things slowly. At 40 years old, you should know what you want and don't want in a partner. And it's really easy to spot the "deal breaker" qualities in someone. I truly believe you know after, or before the end of, a first date if there is any potential for a relationship. If you make a habit out of going on additional dates when you know in your gut that it's never going to go anywhere or if you jump into bed with a woman too quickly, then you might have 'break up' issues to deal with. So the problem is NOT the first date... it's the second date. I don't believe anyone should go on a second date unless the feeling you have after the first date is "I can't wait to see this person again". If the feeling is "meh, I had a nice time... maybe I'll ask her out again and see how it goes" the chances are fireworks are not going to suddenly appear. And, I think I speak for most women when I say we'd rather not be lead on. We'd rather you break up with us than date us out of guilt, convenience, or a lack of courage to end something you started. Just don't get in too deep too quickly and you should have much of a 'break up' issue. 

    Hope that's helpful!  

    Lennie

     

     

    Sunday
    Dec112011

    Do I Break It Off BeforeThe Holidays?

    Dear Lennie,

    I feel like a broken woman. I used to be so strong and held court in my relationships. But, things aren't going well in my current relationship. We fight all the time and I am miserable. The holidays are coming up and it just doesn't feel like the right time to break up. I hate being alone on the holidays and I'm too exhausted to deal with all the drama. What should I do?

    Dear Broken, There is no good time to break up. After Thanksgiving comes Christmas, then New Year's Eve, then Valentine's Day... it never ends. There will always be a reason to stay in the relationship. However, those are artificial reasons. I hate to hear that you feel like a broken woman. That alone should tell you that you need to change things sooner than later. While is sucks to be single over the holidays, it is better than being in a destructive, exhausting relationship. Why not break up, spend some time alone, with friends or with your family. The one thing about the holidays is there is plenty going on and plenty of people to drag you out of a funk and offer their support.