04/04/2013 12:16 pm ET Updated Jun 04, 2013

Ask Michael Cohen: Why Age Matters When Dating

My best friend is 42 and he just broke up with his boyfriend who is the same age. He's now dating a 25 year old guy and it's awful. They have nothing in common and I can't get a clear answer from him about what he sees in this kid. I'm embarrassed for him when we go to dinners, etc., because of the age difference. This kid looks like his younger brother. Is there a way to approach this? Sarah G, Philadelphia

This made me chuckle. The reason you can't get a clear answer from your bestie is because he doesn't want to tell you that screwing a 25-year-old is a good time. I don't believe in this sort of relationship, but putting my personal differences aside, this is not the time to say anything. Clearly the break up has disturbed him and he's having those tedious mid-life issues which for a guy, especially a gay guy, can be horrifying. This kid makes him feel better, for now. These sort of flings usually fizzle out but if in 3-6 months it doesn't, you have my permission to show him the yellow brick road.

I'm a 58 year old divorced teacher at a business school who has been in love with a female student for over a year now. I'm biding my time until she graduates in September, then I will ask her to dinner. She is 35 years younger than I am and my attraction is beyond physical. She is quite unique and somewhat my opposite in term of politics and religion. I'm the liberal agnostic. Yet, I find her so intriguing. Do I need a therapist? Thanks for your advice. Name and City Witheld

You don't need a therapist. You have me and I'm free, at least here. Did you read what you wrote? She's 23! You're 58! I know you are intrigued because she holds the opposite beliefs and perhaps you think this can make for stimulating conversation. It can also lead to knockdown, drag out fights over politics and religion, two sensitive topics. Sometimes in close quarters, we get crushes but you have no basis for a relationship. The student-teacher thing usually doesn't fare well and if she were to date you, she is either a gold digger (I'm assuming as a teacher you aren't a millionaire) or she has daddy issues, none of which are attractive. All that aside, find someone close to your own age, minus a few years if that's what you're into. You'll find a lot more security being on the same page in life with someone who shares your outlook and not discarded at 70 when you can't get it up.

Okay, this is crazy but my parent's divorced last year and both of them are dating. That's not what has me being bitchy. My mom is dating someone 25, which is my age! My dad is seeing a 28 year old girl. It's so messed up. What the hell is going on with my parents? I am about to literally go off on all of them. Tara G, Long Island

This is one of the best questions I have ever received. I want to be you. I wished when my parents divorced my dad brought home some young cool chick instead of my step-mother and it would have been even better if my mom had some hot eye candy around. Listen, you are really over-reacting and you are missing the entertainment value in all this. This is no more than each of them saying f*ck you to each other. This is what divorced middle age folk do. They have tons of sex with the young and ample to make up for the passion they presumably have been missing the past few years. I wouldn't worry about either of these romances going too far -- they always fizzle out just like Demi and Ashton. And hey, if you're single, ask your mom's new boyfriend to set you up with some of his friends, that way you can all double date. Sorry, I needed to go there. Anyway, chill out and I would be journal-ing this experience, it's a movie waiting to happen.

I'm a 22 year old single woman living in D.C. and a graduate of Georgetown University. I work on Capitol Hill and don't have financial issues, but I am not attracted to men my age, I like them older. I typically go for men around 40. I find them stable and reliable, except they don't seem to respect me. They want to use me for sex or they think I am after them for different reasons. Name Withheld, Washington, D.C.

This must be a D.C. thing. I went to American University and I too always liked older guys, reason being I had issues and so do you. Of course they want you for sex, you're 22. No one told me that so take my advice, find your own stability and enjoy making your way to the top of Capitol Hill. You sound like a smart, determined girl who should put her energies into her career and friendships, not some guy who is looking to appease his own needs and you might want to think about the "different reasons" you assume a "stable and reliable" man thinks you're after him for.

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