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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 Tips (7)


    In hot pursuit

    What should a guy do when a girl over-pursues you?

    Well, normally what men seem to do is just ignore the woman and not return her calls or texts. But that’s a rather rude way to tell someone to back off. If you really feel that she’s being overly aggressive in pursuing you and you’re not interested in dating her, then the best thing to do is to be honest and direct with her. Tell her point blank that while you are flattered by her interest, you’re just not feeling the same chemistry. She may get upset by this, but in the long run she will thank you (maybe not to your face, but in spirit), because you will have saved her from greater embarrassment of being that desperate woman who chases a man. We’ve all been there. It ain’t pretty.  


    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.



    Last Minute Cop Out

    Dear Lennie, should I be offended is a guy cancels plans last minute and doesn't apologize or give a reason?

    Offended? No. Extremely cautious? Yes. I am assuming he either cancelled by text or by voicemail, because you would have had an opportunity to ask him why if you actually spoke to him on the phone. While you could ask 'why' in a text, you're more likely to just say 'no prob' or something benign and non-confrontational like that. If he did not offer up a reason and apologize, I would not contact him whatsoever. Wait for him to contact you. If he does not contact you within 48 hours, assume he never will and that he was wimping out. Clearly he doesn't value you. If he contacts you later than that, it had better be a death in the family (heaven forbid) that stopped him from contacting you sooner. There is no reason for that kind of flaky behavior. And, if he's going to be that flaky and disrespectful before you even start dating, why would you want to date him?


    Get Over It?!?

    Dear Lennie: About 5 months ago my boyfriend of 5.5 years and I broke up on very bad terms (he cheated, we dont talk AT ALL anymore). How do I get over him? Its been a few months but I still get sad sometimes when I look at pictures of us and think about him. I just need to get over him but I'm not sure how...im only 20 but I feel like I wont be able to trust any guy anymore. Help?

    Dear Cheated, there is nothing harder than getting over someone. I cannot propose any quick fix that will take the loneliness away. But, you must remember why you broke up. He violated your trust! Here's what I would suggest. Take all the photos, burn them on to a DVD, put them in a box if they're hard copies, and mail them to yourself care of a friend. Delete his number, email address, etc... if you want them for safe keeping incase you want to reach out in the future, then stick them in the box as well. Tell your friend to keep the box for you for a year and not to give it back to you until a year from the post marked date. That way you will not be tempted to fawn over the good memories.  You are only 20 years old. This was your first love and it was a long one, and I do not mean to discredit it in any way. It was important. Necessary. But you are just becoming a woman, you have so much to learn about the world and yourself, and you will look back on this in years to come, you will still remember the good times, but trust me when I say you will look back and know that he was not your destiny. And, if he is your destiny, several years from now, the universe will bring you together. But assume that's not the case. Move forward, keep yourself busy, hang out with friends, date... have fun. Focus on your life, your career, and the right relationship will come.  Email me in a year. I want to know how you feel then! Big hugs. I was in your shoes once. Head over heels with my first love. Now I know it never would have worked... he was far too boring for me. And I've become more woman than he could ever handle. You are young and have your life ahead of you. Go live it! As for trusting other men... that will take time, and you will learn so much as you grow as a woman. 


    Where's This Going?

    I've been dating this guy for two months and we haven't had "the talk" yet (ie: where it's going). The weird part is that I enjoy dating him, but I don't feel like we are in boyfriend/girlfriend territory yet. If I don't feel serious about him yet, is it time to move on? Or do I need to give it more time?

    Sounds to me like you gave it two months. That's plenty of time to know if something is going to work or not. I don't think you need to "talk" about where it is going if it's not there by now. If you don't feel serious about him after two months, what makes you think you might change your feelings in another two months? Be careful not to waste time in a relationship of convenience that is not going anywhere. You can lose years of your life that way. I say cut your losses and walk away. If he's crazy about you, he'll chase after you and that may provide you with the assurance you need to feel serious.