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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 Dating Advice (18)


    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!  





    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. 


    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! 


    My X Slept With My Friend!

    Dear Lennie, I recently broke up with a guy I'd been seeing for several months. He was crushed. He's constantly texting, wanting to see me, even though I told him not to contact me. The next thing I know, he sleeps with my best friend. Only, she didn't know it was him, because she only knew him by his nickname. You know like Jonathan vs Jack, Robert vs Bob, or Bill vs William, and she didn't know his last name. She thought the guy was acting kind of weird, and after it was too late, she pieced it together and called me immediately. The next time he texted, professing his live to me, I asked him if he'd slept with anyone since we broke up and he said 'no'. LIAR. I am not upset with my friend. I believe she didn't know, but I want to strangle him. 

    Dear Strangler,

    Wow. Well, that does deserve strangling, though I still say step away from the rope! Nothing good ever comes from any kind of vengeful act. This guy is childish, vindictive, and a bit of a sociopath. Clearly, he wanted to hurt you and get your attention. Not sure why he is now denying it. Perhaps, he regrets what he did, hopes you don't know and still wants a chance to reunite with you. This sends chills down my spine. It reminds me of an old movie called Sleeping With The Enemy. I say mark his number "do not reply"  and never respond to his texts, calls, or e-mails.  Consider yourself lucky to have learned this about him now, and not years later after you're married to him and have children with him. Take the high road, walk away, and never look back.


    Snooping Through The Phone

    Lennie, My boyfriend is having intimate conversations with a woman that he works with. I discovered it by...unsavory means. I went through his phone. We've had fights about trust and privacy before, and both agreed never to 'snoop' through each other's emails and phones. However, I have suspected he feels something for this woman for a while now, and was too tempted when he left his phone out on the table. What do I do? I want to scream at him about his 'textual' tone, but I think he'll be just as livid with me.

    Dear Snoopy, the fact that you distrust your boyfriend and feel a need to spy on him says it all. Either he is not trustworthy, or you have trust issues, or both. Once that level of trust is gone, it's almost impossible to get it back. Once a snoop, always a snoop. Now that you found something, you will always be tempted to look again. I think you should work on your trust and self-esteem, and make sure that this boyfriend is someone you can trust and stay with for the long run. Maybe there is some incident in your past that is preventing you from trusting.

    In regard to discussing your feelings about what you read, that's a time bomb. If you address it, he will know that you spied on him and then he will not trust you. You see how this works?

    If you can address your concerns about the woman from work in another way, perhaps if he mentions her, and you can truly say "you know, you always sound different when you talk about her. Do you have a crush on her? Should I be worried?" But, you know, that you are never going to have a satisfactory answer.  The flirting he may have done may have been innocent with no intent on follow through, but you may never be able to believe that even if he admits to you that it's just innocent flirting.