DR. WALLACE: I'm feeling uncomfortable about a situation I found myself in the middle of recently. My little sister is only 15, and she is allowed to date once a week as long as the date is chaperoned.

I'm almost 17, so I've been dating for quite some time now. Apparently, one of the star athletes at our high school has taken a sudden liking towards my sister. He's a senior and will turn 18 in about three months.

My younger sister wants to go out on a date with him and wants me to be the chaperone, but she doesn't want our parents to know who she's dating. I've spoken to this guy at school and also texted him several times telling him that I think it's inappropriate that he dates my sister who just turned 15 three weeks ago. He keeps pressing me to be their chaperone, and I keep telling him no.

I thought my forceful negative replies to each of them would end this and wrap up the discussion, but that's certainly not the case. To make matters worse, my younger sister is now begging me every day to set this date up for her. I know in my gut it's not a good idea, and I don't want to deceive my parents. What can I do to get out of the uncomfortable position I find myself in? — I Don't Condone and Won't Chaperone, via email

I DON'T CONDONE AND WON'T CHAPERONE: Under no circumstances should you engage these discussions any further.

It's time to go to your parents and tell them that your younger sister is interested in dating this guy and that it makes you feel uncomfortable. From there, your parents can step in and talk to her.

In the future, when you know a situation is not good at its core, such as the deception your sister and this guy are striving for, you owe it to yourself to announce this to all parties immediately, rather than letting the situation fester as if you may change your mind under the duress of persuasion.

I DIDN'T TREAT HIM AS HE DESERVED

DR. WALLACE: I'm a 16-year-old girl who fortunately has a lot of friends at my high school. I'm lucky that I've had a lot of opportunities to date, and after shuffling through a half-dozen brief series of dates with different guys, I found someone quite compatible. We've been dating for the last 3 1/2 months.

However, I've just this past week started to realize that I've been taking him for granted and being a bit pushy and condescending to him as well. He really doesn't deserve that, and although I can see that at times he's disappointed, he's been polite and nonconfrontational despite my intermittently inappropriate behavior.

After doing some deeper thinking, I think I'm realizing that in the back of my mind, I know that if we break up, I'll be able to find another date within a reasonable amount of time, but there's no guarantee I'll find someone that treats me as well and connects with me as well as he does.

I plan on adjusting my behavior, but I'm wondering if I should say anything at all or apologize to him for my past behavior or if I should just let my new behavior stand on its own. What do you think? — My Soul Searching Caused Positive Adjustments, via email

MY SOUL SEARCHING CAUSED POSITIVE ADJUSTMENTS: I recommend spending a full week engaging in what you believe to be your very best behavior before you bring anything up.

Then, when the time is right, mention that you had time to reflect upon this relationship and his outstanding personality, and let him know that you realized how much you value him and that you realized you weren't behaving very well. I feel your words will carry more weight once you've demonstrated, rather than just talked about, the new leaf you feel you are turning over.

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 www.creators.com.

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