10/26/2013 11:32 am ET Updated Jan 23, 2014

Ask Michael Cohen: When Honesty Goes Too Far

I've been dating a great guy for three months now but I'm still in communication with my ex of seven years. We speak at least once a week, about everything from our mutual friends to how are careers and families are. Is this wrong? Should I stop sneaky around and tell my current boyfriend? Lauren K, Colorado

Aww, how sweet, you talk about friends and family with your ex; this is not the AT&T plan. I don't think you should be communicating with him like this because after all, he earned his title. Slow your roll on the phone calls and give your new relationship time to prosper. Most importantly, do NOT say a word to the current boyfriend. You may not know this, but men get extremely jealous. If you can't stop these shenanigans with your ex and hang up, you may wind up in a current break up.

I was up for a promotion at work and just found out that I got it. The problem is my co-worker who is a good friend of mine also interviewed and obviously didn't get the promotion. The position doesn't start for two weeks. Should I tell her before I get out of my cubicle and into an office with a view? Name Withheld, New York City

Get it over with and tell her quickly or whomever did the interviewing will break the news first; leaving your friend wondering who got the promotion. Of course, it's going to be uncomfortable, but it will only last a few minutes. Do it face-to-face, not over email or text. If your good friend is the person you think she is, it should go smoothly. If not, at least you will be able to go into your new office and shut the door.

My sex life with my boyfriend is not working out like I had hoped. Here is why: he has a small penis and I'm not satisfied. There are just so many times I can have oral sex and fake an orgasm. My girlfriends say I am crazy and he is a good guy. I'm torn.
Name Withheld, New Jersey

A small penis is no bueno. I'll admit, I've ditched a few guys for that exact reason. It's one of those situations where the truth is dreadfully painful. Do what I did -- tell him you just don't feel the chemistry. He doesn't need to know that you just don't feel him...literally. As for your girlfriends and the "nice guy" shtick, it's terribly boring and totally irrelevant to your vagina.

One of my friends is slightly overweight. I don't have a problem with, but I do have a problem with the way she smells. I can barely get close to her sometimes. Her car smells and so does her apartment. I noticed the problem is getting worse as she has gained some weight recently. What should I do? Liz M, New York

This question is so big and so sad. I suspect your friend doesn't know how to take a proper shower and when you're overweight you really have to wash between the rolls. The answer to this question is tricky because a good friend should never let another be embarrassed and/or ridiculed, which I imagine is happening. Just know that this may be a situation when honesty may be the best policy, but the hardest to execute. It may rock her, but I am sure (or I hope) that she appreciates the love down the road or the Marc jacobs perfume that magically appears on her doorstep!

Need advice on how to handle your next dilemma? Ask me anything. Leave a comment below or email at

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