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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 First Dates (4)


    I Thought He Was Into Me

    Hey LennieI went on a first date with a guy and it was great. He was handsome, charming, picked up the tab, dropped me off, no creepy factor, and so on. We mentioned that we would try to meet again for lunch the next week, but I never heard from him. I called once and texted a few times, but never heard from him! I want to see him again. Should I contact him again or will I look desperate? -Sleepless In Los Angeles

    Dear Sleepless,

    It's like the movie 'He's Just Not That Into You'. I wish I could tell you otherwise. Perhaps the date didn't go as well as you thought, maybe he sensed some kind of deal breaker. Could be that he's just a flake after all, or he's playing the field. Anymore contact will just make you look and feel desperate and won't likely yield positive results. Time to move on, you deserve better!




    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?


    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.