06/29/2010 11:33 am ET | Updated May 25, 2011

Ask Michael Cohen: Dirty With Rich Hair

I have been going to the same hairdresser for the past five years. We have always had open conversations but recently he's taken it to another level. While he has always told me about his gay trysts the last story about threesomes and penis size was too much. I pay $150 per haircut, and I don't feel I need to listen to this. What should I do? I don't want to tell the owner, who also happens to be a gay celebrity. He probably tells stories like that too. Tell me what you think and how I should handle the situation. Name Withheld, New York City

If I were paying $150 a haircut I would tell my stylist to think of me as a sculpture that was to be exhibited at The Metropolitan Museum of Art and not as just another overpaying rich client, who thinks her gay hairstylist's stories are interesting, when in fact they are so 1980s boring.

Though in theory it would be nice to say this to your stylist's face, I know in reality few of us have the courage to do so. However, I don't advise people to wimp out of situations. So if you can't go there, at least let your stylist know you won't be returning, and tell him the truth gently: you need change. In fact, this is a good opportunity to make a change, because there is always someone smarter, better and, well, bigger out there.

I moved from Ohio to the Upper East Side of New York City last year. I was so excited to be in the city, and after only a few months I met and fell for a girl that I'd been eying at the gym for weeks. For a while everything seemed to be going great, and we had a freaky sex relationship. She likes it when I say things to her in bed like "oh daddy's little girl is bad tonight," and that's just the beginning of it. Now she wants us to head out to swingers clubs. I was thinking about asking her to marry me, but this is all too much and I wanted to know if you are familiar with this type and give me some straight up advice. Thanks. Bradley, New York City

Am I familiar with this type? Yes. I grew up with girls like this, went to sleep-away camp and college with them, and finally ditched their absurdity when I became an adult. There are two things you need to know about Upper East Side girls: They are either twisted bitches or frustrated prudes. Either way, you're screwed, though with the latter, not literally.

So clearly you must understand that she has daddy issues and while her sexual behavior may be cute and hot in one of those swinger parties, where everyone bangs daddy's little rich girl, it's really unhealthy for this relationship. Trust me, it's never going to get better unless between the gym, botox and sex, she gets a lobotomy.

I think if you are looking to settle down, in this case opposites don't attract. Find yourself a nice Ohio girl in big bad New York City.

Ever since Cate Blanchett cut her hair I've wanted to do the same except my husband really, really loves my long hair. He's always telling me how good it looks and I have to admit, I do love when he pulls it. But, on the other hand, it's been years and I'm just ready for a change. I have plenty of time to plan this out since he is a doctor and not home all the time. Will this crush my husband? How to do it? Help! XX Theresa P. Summit, New Jersey

I sense you've made your decision and you just need a little boost of confidence. The first thing is don't ask or tell your husband about the upcoming sheering. Make an appointment for a Friday afternoon, and when you get home put on your sexiest outfit. I'm talking La Perla lingerie and sexy Gucci dress.

When he walks in that door, you own that haircut. Don't ask if he likes it, loves it, whatever. If fact, don't even discuss it. Just welcome him home to the new you.

You can submit your questions on my website or in the comments section here.