Ask Lennie

Break Up Phobia

2012-04-01T07:01:12Z

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!

Lennie

How Do I Say It's Not Working

2011-12-18T08:02:35Z

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?

2011-12-11T08:02:00Z

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?

2011-12-04T08:01:50Z

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?

2011-11-27T08:01:51Z

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.

Gun Shy

2011-11-20T20:00:00Z

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.

Is A Threesome A Good Idea?

2011-11-13T08:02:02Z

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?

Once A Cheater Always A Cheater?

2011-11-06T07:01:14Z

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.

Boss Crush

2011-10-30T07:01:54Z

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!

The Kids Conversation

2011-10-23T07:01:44Z

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!