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 Women (27)


    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. 


    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?



    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!


    Tired Of Waiting

    Lennie, I was dating a man who is separated, but not divorced and I ended it. He asked me to wait and said his divorce would be final in six months, but it wasn't. I love him, but I feel like I've wasted enough time. I have heard of divorces taking years, not months, and it's just not fair to me. What are your thought? I'm getting old and getting tired of waiting.

    Dear Tired of Waiting, 

    I think you made an excellent decision. You know that expression if you love something set it free... well, he should have had the strength to set you free, not drag you along in the dust of his bumpy divorce road. It took strength to do what you did. You deserve better, and you basically told him so. You need to move on with your life. If he shows up at your doorstep with a ring six months down the road, and you're still available, then you have another decision to make. In the mean time, you are free to do what you want, see who you want, and live your life as the single, unmarried woman that you are. Don't give away your independence for a maybe.


    Am I A Loser 'Cause I've Never Been Married?

    Lennie, most of my girlfriends from college are married, and I'm not. It's like that saying "always a bridesmaid, never a bride." Is there something wrong with me? I just haven't found the right guy, but when I tell them that, they say I'm too picky. I want to get married, I just don't want to make a mistake and end up divorced.

    Dear Never Been Married:

    Reminds me of that movie Never Been Kissed with Drew Barrymore. If I recall right in the movie, she felt the same way about romance as you do about marriage. There is nothing wrong with being single. And, according to a recent article in the New York Times nearly 50% of the adult population in America are single. The sad fact is, as stated in the article, we miss out on all the advantages (tax, medical, etc) that married people have. I think you are wise in waiting for the right one, rather than marrying out of desperation, need, pressure or insecurity. Stick to your principles and your prince will appear.