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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 Dating after (1)


    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!