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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

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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.



    If He's Flirtatious, Is He Interested?

    I recently made friends with a guy from my class and we are very flirtatious with each other. I want him to ask me out or make a move, but I don’t know how to bridge that next step. If he was interested, would he have made his move already, or does he just like flirting with me to lead me on?

    Dear Flirtatious, it sounds to me like he is interested or he would not flirt with you. He may have other things holding him back from asking you out; he could already be in a relationship and just enjoy the harmless flirting, or he could have recently ended a relationship and not be ready for something else. It would be important to find that out. I do think that if he is genuinely interested, he will ask you out. Give it a little more time. If it goes on endlessly, you can either stop flirting back or ask him directly what all the flirting is about. Whatever you do, do not ask him out. Flirty followed by asking a guy out communicates DTF (if you don't know the term look it up in Urban Dictionary).


    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. 


    Feeling Cheated

    Lennie: I go on a lot of first dates and I'm always paying the bill. Rarely do these dates develop into anything more. Why does the guy always have to pay? It's like a rip off and it's not fair.

    Dear Not Fair, life is not a Disney movie. The fact that women make on average 30% less than men and are subject to sexual harassment and sexual discrimination is not fair either. Men pay for first dates (and generally for all dates), because it's proper dating etiquette. I'm assuming that when you say you feel "ripped off", it's because you have an expectation to get to the proverbial "third date" or beyond and are not getting any action. If you're not making it past the first date, perhaps you are asking out the wrong women or there's something about yourself that needs improvement to make them want to take things further. Maybe they are sensing your desire to get to hit a home-run. It's easy to blame others. Maybe it's time to take a long look in the mirror and see if your hair needs a trim or your attitude needs an adjustment. If you feel you cannot afford these dates, then suggest dates that have less impact on your bank account, such as going for coffee or going on a hike. Remember, you have to be wiling to play ball in order to hit one out of the park. 


    Relationship Status: It's Complicated

    Dear Lennie: I made friends with an older man (I'm 30, he's 45) who recently ended an 8 yr relationship. He flirts, sexts, and emails daily, but doesn't want to do anything physical. We have an amazing connection and spend lots of time together, but he says he's not ready for a relationship. I don't want to give up on having him in my life, but he is in my heart and mind and taking up lots of my energy. Should I stay friends until he is ready for more?

    Dear Complicated, when a 45 year old man gets out of an 8-year relationship, he generally wants to be on his own for a while (read 2-3 years). Recently single, older men like to play the field and while he may flirt and show interest in you, he clearly does not want to play you, which means he respects you (a good thing). Don't give him a reason not to respect you by making yourself so available. At his age he may not want to have children or get married and he may look at a 30-year-old woman as someone who wants a family, so he could be protecting himself and protecting you from getting hurt. You may wait a very long time for him to be ready for a relationship, and there are no guarantees he'll choose you. I say be friends, but go on dates with other men and play the field yourself. If it happens with him, hooray! But, even if it does, I'd be very aware of addressing the age difference and desires to have/not have a family, marriage, etc early on so that you don't get your heart broken. Don't forget to think about the age difference later on, when you're 45 and he's 60.


    The Fake Wallet Draw

    Dear Lennie, At the end of a date, even if I am expecting the guy to pay, I feel like it's rude or presumptuous of me not to at least pretend to go for my wallet. What is the most graceful way to handle someone paying for you? Feeling guilty.

    Dear Guilty Girl: I don't recommend the fake wallet draw. He may take you up on it, and if you weren't actually intending to pay, you may be embarrassed if you don't have enough cash on hand. Furthermore, he may pick up on the fake draw and that's not going to impress him. I'm a traditionalist when it comes to dating and believe a man should ask a woman out and pay for the date. His manners and dating etiquette are an indication of how caring he will be as a partner. The most graceful way to handle someone paying for you is simply to say "Thank you" or, you can elaborate and say "Thank you, I had a lovely evening." If you are uncomfortable having a man pay for you, you need to examine why. It could be a lack of self-respect or self-worth that you don't feel deserving of being treated well, or it could be that you feel an obligation to take things further. Make no mistake: Your only obligation is to act like a lady. If you act like a lady, you deserved to be treated like one too.