10/14/2011 01:32 pm ET Updated Dec 14, 2011

Ask Michael Cohen: How to Have an Affair

For the past two months I have been having a full on affair with the father of a daughter at my school. I know, this is like a cardinal sin, literally, considering it's an all girl's Catholic school. The affair started because he is a divorced, stay-at-home dad who dabbles with the stock market until it's time to pick up his little girl. So, not only do we see each other everyday but now we meet at different hotels all over New York City at least three times a week and text each other 24/7. For me, it's going somewhere serious. For him, I'm really not sure and don't know what to do at this point. Name Withheld For Obvious Reasons, New York City

I'm here to give you a serious reality check sister; it's been two months. Big deal. If you were to tell me this has been going on for two years I would be concerned and tell you to do double time on those prayers. But for now, this sounds like a wonderful affair He's a hot, rich daddy that makes crazy love to you all over New York City. What exactly is the problem?

I'm tending to think your emotions and life plan are getting in the way of pure unadulterated fun. My advice is don't think so much about it and enjoy the moment. And by the way, I strongly urge you not to fantasize that this is the only guy in the world and that one day you may be this little girl's step-mom, which I feel has already crossed your mind. Have the affair, have the fun and make sure the thread count at said hotel rooms are up to par.

My girlfriend recently finalized what was a really horrid divorce. Both are big family names from the towns they come from. Now that the dust has settled, we were thinking of throwing her a divorce party. What do you think of this idea? Olivia W. Dallas, Texas

One word comes to mind: bitter. A divorce party, really? Like some victory party or is this something akin to a sweet sixteen? Not so much. Try this for celebrating. Be a tried and true friend not because she has made it through a public spectacle of a divorce, but rather because your friend found the strength and gumption to make a change in her life for the better. Getting a divorce from anyone or anything whether it's a business partner, lover, family or friend requires the utmost strength emotionally, physically and mentally and your constant applause for your friend is the best party.

But I do have an idea. And I must give credit where credit is due. A close friend (if it makes you feel better, she is a really, really big name) just had her own horrid divorce and as a little something special to herself, she bought what she calls a "divorce ring." Hers consists of three intertwined bands, one representing herself and the other two each of her daughters. Every time she looks down it reminds her of the wisdom and courage it took to change her life. Now that's something to drink too.

I recently have been out of a job for some time now and had a fabulous interview. When I was called back for the second interview it was to meet with someone who would be a co-worker on the project or as the boss said, "partner in crime." Well, he wasn't kidding. It was infatuation at first sight, on both our parts. Needless to say I got the gig and my first business dinner with my co-worker was spent in his bed. I'm very confused about what to do. Have an affair with someone I work with or don't? Layla C, Chicago

One side of me thinks like the gay guy I am, wow girl, cha-ching! You got a job and got laid and it didn't involve any street walking. I mean, seriously, you put Julia Roberts circa Pretty Women to shame. Now, my bible belt makes me question your morals, yet my c'est la vie side makes me wonder why we put so much energy into questioning what life brings us.

But you have asked whether to have an affair with a co-worker or not and the answer is no. Why? Because affairs end, and they never do so amicably. Someone is going to get hurt. I am afraid you may get hurt twice; firstly because your emotions are on the line, and secondly because you're the new girl on the block at work and a few bad words from your co-worker to the big boss and you can say au revoir to this gig.

It's time to keep it professional and honest. Tell your co-worker the truth. This isn't a healthy thing for either of you because of the reasons mentioned above. But do be thankful for the hot sex. All that flirting and sexual frustration for months to come would have gotten really tired, really fast.

Want to know how to do it right? Leave me a question here in the comments section or email me at