MillionaireMatch.com - the best dating site for sexy, successful singles!
MillionaireMatch.com - the best dating site for sexy, successful singles!

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

More of Lennie's books »
Book recommendations, book reviews, quotes, book clubs, book trivia, book lists
Search Lennie's Site
Follow Lennie

Now Available!
For International sales or larger orders, please contact sales@lennieross.com
Contact Lennie
This form does not yet contain any fields.

    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 Advice for Men (12)


    The next step

    Our relationship is going well and steady for 6 months, and she’s talking about taking the next step, but I’m not ready. What do I do?

    The answer to this question depends a lot on the age of both parties involved. The older a woman gets the more time-conscious she becomes, partially due to her biological clock. Men seem to think they can stay young forever; women tend to be more realistic. Regardless of age, it’s not healthy to be in a relationship just for the sake of being in a relationship. If you are not ready to take things further, you need to examine why that is. Are you not ready to get serious with her or are you not ready to get serious with anyone? You need to be honest with your girlfriend about how you feel, even if it means ending the relationship or taking some time apart to figure out what you want. Be forewarned: if you opt to take time apart, she may move on while you are trying to decide what you want, so don’t take too long.



    Shape up!

    Dear Lennie, How can I get my girl to go to the gym without pissing her off and making her self-conscious?

    Women are very sensitive about their physical appearance. You want to make sure to approach this the right way so that she doesn’t feel unattractive around you (bye-bye sex life). A great thing to do is to say that you need her to help you get motivated. Such as “I want to sign up for this boot camp class but I don’t want to do it alone. Will you come with me (insert puppy-dog face)?” Another tactic is to tell her that you want to get outside more and invite her on a hike, taking the dog for a run, snorkeling, surfing or diving lessons, a weekend trip to a national park. If she complains that she’s depressed you might want to share research with her about how exercise is universally recommended by psychiatrists, and it’s a great first step to feeling better and boosting your endorphins. This way it isn’t about her body, but her well-being.


    Why is she unwilling to commit?

    Dear Lennie, I’m dating a girl, but she won’t commit to a relationship. Why?

    Dear Dating, define relationship, would be my first comment. If you mean she won’t have sex with you, that’s one thing. That mean’s she likes you, she’s very interested and she doesn’t want to have sex too soon for fear that you will just see her as a fuck buddy. Or, it means she sees you only as a friend and has no interest in ever having sex with you. In which case, I have news for you: you’re not dating. If you mean, she won’t get serious as in talk about the future—marriage, children, and a life together—I hate to break it to you, but this means that she is not convinced you are the man for her. Maybe she can’t see herself having children with you, maybe she doesn’t feel financially secure enough in the relationship—envisioning herself having children, losing her salary for a period of time, if not indefinitely—and worries that you don’t earn enough to put the kids through college, etc. One way to find out if she’s serious is to pull out a ring and propose to her. 


    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.  


    She asks, he pays?

    If a girl asks me out on a date should I still pay?

    If this is the beginning of a relationship, and a woman asks you out, you’re obviously under no obligation to pick up the tab. However, you do want to leave a favorable impression. The reason she may have asked you out is because she is really interested in you and didn’t have the patience to wait for you to make the first move, or was concerned that maybe you wouldn’t. It’s amazing how passive men have become about asking women out. It’s as though they fear being shot down. That said, the polite thing to do is to offer to pay. However, if she insists on paying, then respect her choice. She may have her reasons—one of which could very well be she wants to control the pace of the relationship (ie: don’t expect to get laid any time soon).