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.



    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!  





    How Do I Say It's Not Working

    Dear Lennie: I've been dating this guy for three weeks. We tried to have sex for the first time last night, and I'm not interested in trying again. I saw meds in his bathroom—happy pills that make dicks limp. And I didn't like the smell of his linen or of him. So how do I say no thanks? I don't want to hurt him, but it's not working. I'm done.

    Dear Done:

    Honestly, this may sound harsh, but if the shoe were on the other foot, do you really think he'd care about hurting your feelings? It's only three weeks, you're not exclusive, you just had sex for the first time (bravo for waiting, btw). If there is no chemistry, you don't owe him an explanation, and you don't need to let him down easy. Just tell him you're not feeling it. If he ask for clarification, just say "not feeling it, is not feeling it. There's nothing more to say". You don't need to get into a whole drama about seeing the meds, or not liking his body odor, or any of that. That will become hurtful and a big heated conversation. If you're afraid of confrontation, you could do it in an email or text, but that's really taking the easy way out. Just pick up the phone and say "it's not working". 


    Do I Break It Off BeforeThe Holidays?

    Dear Lennie,

    I feel like a broken woman. I used to be so strong and held court in my relationships. But, things aren't going well in my current relationship. We fight all the time and I am miserable. The holidays are coming up and it just doesn't feel like the right time to break up. I hate being alone on the holidays and I'm too exhausted to deal with all the drama. What should I do?

    Dear Broken, There is no good time to break up. After Thanksgiving comes Christmas, then New Year's Eve, then Valentine's Day... it never ends. There will always be a reason to stay in the relationship. However, those are artificial reasons. I hate to hear that you feel like a broken woman. That alone should tell you that you need to change things sooner than later. While is sucks to be single over the holidays, it is better than being in a destructive, exhausting relationship. Why not break up, spend some time alone, with friends or with your family. The one thing about the holidays is there is plenty going on and plenty of people to drag you out of a funk and offer their support.


    Friend Date To Company Xmas Party?

    This guy I know who is a lawyer—we're friends—asked me to be his date to his work Xmas party. I don't want to date him, but I thought it might be a good place to meet someone. Thoughts?

    I can see the appeal of going to a party with a bunch of successful attorneys. Good fishing pool! However, it can be awkward to go as this fella's date to his company holiday party if you're not interested in him. First, it may send the wrong message to him. He may think you are interested in him. And, those who see you together definitely will assume that. You will ge more attention if you go to events alone or with a girlfriend. Make sure your friend is not single or likes a different type of guy than you, or you may end up competing for the attention of the same great catch and that could put a strain on your friendship. 


    Why Did You Get A Divorce?

    Lennie, I'm a divorced, single dad with greatest son in the world. I'm always asked by dates "Why did you get a divorce?" I don't feel discussing my ex would be in the best interest of my son. I try to answer honestly and tactfully: Divorce was not my idea; I never cheated / lied / ran-off with cheerleaders, etc.; further, my son knows he has two parents who love him more than anything. Dates consistently dig for more. They want a reality-TV back story. I don't badmouth, instead I say we had different values and steer the coversation to my values. I would not probe them about their old boyfriends, yet my answer is not enough for them. 

    Dear Divorced Dad,

    If a woman is looking for the drama version, she is probably accustomed to drama. Your answer to the probing is clear, concise, and respectable. It can be a threat to some women if you have a flawless relationship with your ex, but that doesn't seem to be the case, it seems more like a mutual respect for the sake of the child. Very mature. Talking about the "ex" is an easy topic (yet not graceful) when trying to get to know someone, so makes sense it would be asked often. I think your high road approach and decision to be a bit private is wise. It could be these women lack trust and lack experience with relationships that ended on good terms. Perhaps these women need to grow up a little before they are ready for a solid man like yourself.