Move On From His Creepy Request -- And Him

By Dr. Robert Wallace

June 12, 2020 4 min read

DR. WALLACE: I've met a good-looking guy, and we've been dating for almost a month. We are both 17. He's pretty friendly and normal, and most of my girlfriends are jealous. But whenever we go out somewhere alone on a Saturday afternoon, he asks me to take my bra off and just go with a more "natural look."

Don't get me wrong; he has not tried to touch me in an inappropriate way or anything like that, but I'll admit I found his request pretty surprising and odd, especially the way he first asked me to do it. He stopped at a gas station to put fuel into his car and asked me to go into the gas station bathroom to take my bra off so I would only be wearing my sweater with nothing underneath!

I told him no because I was uncomfortable both with a dirty gas station bathroom and not wearing a bra in front of him. I found this whole incident creepy.

So, when we went out again the next weekend to take a walk on a hiking trail, he told me that he'd go 50 yards up the trail alone to give me a few minutes of privacy to take off my bra under my T-shirt. I did not take my bra off; I just waited a minute for him to go ahead, and then I joined him without saying anything. He glanced at me when I caught up to him, but he didn't say anything to me about the fact that I left my bra on.

What can I do to cool his aggressiveness with this matter? I'm getting more uncomfortable about these requests the more I think about it. — Fully Clothed, via email

FULLY CLOTHED: Forget about how good you think he looks, and focus instead on how he makes you feel. Your own words have indicated to me that you are uncomfortable around this young man, and since he has made this unsavory request of you on multiple occasions, it's clear this is not a mistake or poor attempt at a joke. He likely wants to see how far he can push you into doing what he wants you to do.

I suggest you follow your instincts, which are subtly warning you to stop seeing him. Making you feel uncomfortable about such a personal issue early in a relationship or friendship is very wrong.

The best way to end your discomfort here is to break up with this guy. I suggest you move on now, before he comes up with a different request, one that you would probably be better off never hearing.


DR. WALLACE: I'm 19 and have an illness that, unfortunately, is hereditary. My doctor told me that if I ever have children, there is a 50% chance my children might suffer from this very same illness.

Should I inform the girl I'm dating about this, or should I wait until we discover that we really care for each other and then tell her? — Dicey Genes, via email

DICEY GENES: Wait until at least a half-dozen dates. By that time, you will know a little more about this young lady and her personality, and she will similarly know that same amount more about you.

I see no need to rush this, but at the right time, in the near future, she does deserve to hear this from you.

The good news is that modern medicine is always improving, and new treatments and cures are constantly being developed. Since you're a young man, there's a chance some meaningful progress might be developed that could positively impact your situation.

Dr. Robert Wallace welcomes questions from readers. Although he is unable to reply to all of them individually, he will answer as many as possible in this column. Email him at [email protected] To find out more about Dr. Robert Wallace and read features by other Creators Syndicate writers and cartoonists, visit the Creators Syndicate website at

Photo credit: nastya_gepp at Pixabay

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