16-Year-Old Wants 28-Year-Old Woman

In Dating, Drama on March 8, 2010 at 8:11 pm

When Ashton Kutcher was 16, his wife, Demi, was 31!

Hi Yenta,

I’m 16 and i finish school in 6 weeks. In my last year i have had a great teacher who is Jamaican and immensely interesting, she is the most beautiful woman i have ever met in my whole life. She is 28 and has a 9-year-old kid. We share a lot in common, like we were both going to join the army and we both like the same music and stuff like that. Now i know this is wrong me asking her out but my question for you is how can i ask her out just as friends?

I know this is morally wrong but i like her a lot and she isn’t married so i would not be interfering with her life, she is not seeing anyone else either so it would be ok for me to see her. Also i would like to ask you two more questions.

Even though i am very confident around her and think i stand a chance with her i always tell myself “do not ask her out when you leave” because it will be wrong and awkward. i’m set on asking her out because i always think “what could have happened if i did ask her?” How do i remove this feeling from myself? I know full well that i have nothing to give her apart from security honesty and an un-dying loyalty but how can i convince her that although i may be a really young guy i deserve a chance at least.

Thank you in advance,


Dear Jamie,

It is not “wrong” to like your teacher, nor is it wrong to want to hang out with her. In fact, according to, “Dating someone without sexual contact cannot be considered a form of statutory rape, and is almost never illegal.” It makes sense that your beautiful teacher with many things in common with you would be someone who stirred your heart.

But just to help you understand why she might say “no” if you go knocking on her door, a few main points as to why a sixteen-year-old might not be the best mate for a twenty-eight-year-old with a nine-year-old child.

1) I think, if your beautiful teacher were to ever kiss you, it would actually be illegal. Last thing you want is to make your teacher a jailbird, leaving her kid motherless.
2) Even though she seems like the woman of your dreams now, the truth is there are twelve years of complex life between you. She has been in the world in a different way, and while loyalty and honesty are amazing traits in a man, understanding one another on a deeper level is also vital to a strong adult relationship. You may not be able to understand certain things about her life, and she might not be able to understand yours.
3) Even if you DO understand everything and have the maturity of a forty-year-old man, you still might not be the best candidate to father a nine-year-old boy. Yes, having a father only seven years your senior might be an awkward life experience. And your teacher, I have no doubt, will be shopping for a Dad in the men she dates.
4) Aren’t there a million sixteen year-old girls with no babies who want to hang out with a loyal and honest man?

Connecting to a teacher in high school can be powerful because sometimes they are the only people in your world who see you as an adult, who verbally praise your good mind, and who show great interest in your growth and well-being. Don’t, however, underestimate the force of hierarchical relationships on the heart. Somehow, these power-laden ties create strong complicated desires in both parties. This, though, may not be “love” as much as projected daddy/mommy issues.

So, my sixteen-year-old friend, this means you need to check in with your lonesome and see if you might be having trouble at home, issues with your own parents, a loss, a gap: something that ups the appeal of your prof.
My guess is that you are phenomenal. Be patient and know that while this woman might seem like the only one of her kind, and she very well may be, in due time you might find others who stir similar feelings in you.

You also might find that once the limits of teacher and student disappear, that your differences suddenly swell. All in all, I would say there is no harm in asking. You can say, “Teacher, I would like to hang out with you as a friend.” There’s no sin in that question. But be prepared for whatever answer she gives, most likely, a “no.” Don’t be broken-hearted, she needs to keep her job and stay out of jail and you need to look for women your own age, rather than mother-hen figures who might not be the romantic you are really going for.

Another thing to keep in mind: if you are, say, 23 and she is 35, then this relationship might be a wee bit more acceptable. Stress on the “wee bit.” If you think she is the love of your life, wait for her. Here, whatever you choose, use this CNN article, “Older women and younger men: Can it work?” to back up your case. She is lucky to have your devotion, even if she can’t take it home.

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