Sponsors

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!
ebook
paperback
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.

     

    Sunday
    Nov202011

    Gun Shy

    Dear Lennie, I am in immensely in love with a woman who builds walls around herself. She dumped me 3 months ago due to external commitments, but I still love her. I really think it was that I didn't make enough money, even though I make $.25M a year.  Little by little and by charm and caring we are now seeing each other. We went out on a date last week and had a really great time again. We are now emailing every day and talking every day. She ended a letter to me by saying "I love you". As a guy do I let this go and play cool, or do I tell her I love her all over again. I do love her but I want to keep a little distance before we go any further again. A little gun shy now!

    Dear Gun Shy, its never fun to open your heart and risk getting hurt. Especially a second time! Tell her that you love her, but that you also feel vulnerable and don't want to get hurt again. Take things slow. She will appreciate the honesty, and the vulnerability, and this way you are letting her know that you don't want any more games. Protect your heart, but allow yourself to feel. By the tone of your email you sound like a great guy. It is understandable that women often worry about money, but you do well for yourself. She needs to think about what is important to her. Hopefully she is not a "material girl" who cannot appreciate that there are more important things in life (namely the love and respect of a great man) than Louis Vuitton. 

    Sunday
    Nov132011

    Is A Threesome A Good Idea?

    Lennie, my guy wants me to have a threesome. I'm scared it will ruin our relationship. I want to keep him happy, but I'm scared this will become a slippery slope of debauchery. Should I or shouldn't I? I like monogamy.

    Dear Monogamist, Your question is difficult to answer as there are many variables. I am a firm believer in keeping things spicy in the bedroom, and if adding a third party, or even a fourth party will do that, then why not. That said, it depends on the emotional security and self-esteem of the people involved. If you are easily jealous and will wonder if he's engaging in other extra-marital or extra-relationship activities, then a threesome is probably not for you. I think sex is sex and love is love, and that the two can be separate with a very secure couple. However, one often doesn't know how secure/insecure the other is until they test the strength of the relationship. Sometimes keeping someone on too tight a leash will lead to more temptation for the leashed person and ultimate betrayal. Sometimes the "idea" of a third party, and just flirting with the idea, is fantasy enough to ignite things in the bedroom. Clear as mud, right?

     


    Sunday
    Nov062011

    Once A Cheater Always A Cheater?

    Dear Lennie, My ex and I are still pretty good friends. We have been friends for forever and dated for 3 years. He cheated on me, a lot, so obviously things didn't work out, but we still hang out from time to time. Anyway, every time he sees me he tries to get into my pants. Well, long story short we ended up sleeping together and a week later I found out he has been dating some chick for about 3 months and she just found out she is pregnant with his baby. I don't know what to do. Do I warn this chick? Or just let it go and cut all ties with him and those people?

    Dear Cheated, First, let me say "ouch" that's gotta sting double hard! I think you have learned your lesson and won't allow yourself to be used and hurt by a cheater like this again. As for the other woman, if you caution her you will just come across like the scorned ex-girlfriend and will likely create more drama for yourself. You don't owe her anything, and she will learn her lesson in due time. Just be thankful you are not in her position, cut all ties, take the high road and move on. 

    Sunday
    Oct302011

    Boss Crush

    Lennie - I have a huge crush on my boss! He's never made any advances towards me, and he never talks about his private life, so I don't know what his relationship status is (where's Facebook when you need it?) How do I tell him how I feel without....making it weird at work?

    Dear Work Weirdo,

    No matter what you risk making it weird at work by expressing interest in your boss. It's never a good idea to mix work and play, but it happens all to often in the work environment. The average relationship lasts 5-7 months, so the odds are you're going to wind up working for your ex-boyfriend. So think of that first and foremost. If you still cannot help yourself, I would find out the company policy on dating co-workers, then I would try to find out his relationship status as discreetly as possible. Maybe you can find out what he does in his non-work hours and arrange a meet-cute. You know in the romantic comedy movies where the leading couple first meet in some cute way. Do you know where he works out? Where he has coffee? Coincidentally, just bump into him there while looking your absolute best and strike up a casual conversation. If he's interested, he might just give you an indication outside of the work environment. But, whatever you do don't become a stalker! 

    Sunday
    Oct232011

    The Kids Conversation

    Lennie, I've been with my boyfriend now for almost two years. We live together, get along great, and we're talking marriage. There's only one bad thing. When we first started dating, he told me he doesn't want kids! I really want kids, but I really liked him at the time, so I thought maybe over time if we were still dating, things would change. How do I bring up the kids convo again without seeming like a fake who led him on?

    Dear Kid Lover, when a man says he doesn't want kids, he usually means it. Most men speak their mind and don't waffle on important life-changing issues like that. I'd say there is no time like the present to have this conversation. If you want children, and he doesn't, that's not going to change a few years down the road. What's likely to happen is your eggs will be older, and you will be increasingly frustrated and resentful and your relationship may suffer. Get a firm 'yes' or 'no' now, before you waste more precious time. Good luck!