He Asked Me Out, I Said Yes and My Sister Lost It!

By Dr. Robert Wallace

May 12, 2023 6 min read

DR. WALLACE: My older sister is 19 and she has a nice boyfriend who is 20. They get along great and have been dating for a year now.

I'm 16 and had a very unusual thing happen. My sister was out at our local mall and forgot to bring her purse, and since I was heading to the same area, I agreed to bring it to her. When I found her at the mall, her boyfriend had his younger brother with him since he had to buy him some sports equipment. His younger brother had just turned 17 and I got the chance to meet him, shake hands with him and talk to him briefly. I just turned 16 and a half, so we're pretty close in age and even though our conversation was short, it was really nice, and I liked him right away.

The next day I got a text message from this boy since we have some mutual friends who passed my number on to him. I was happy to hear from him, and we texted back and forth several times. We're now planning to go on a date next weekend.

My sister found out about this date, and she wants me not to go! She feels this might cause strain on her relationship, so she wants me to tell this boy that I'm not interested. But I am interested!

She also told me that if I don't call the date off, she'd have my parents cancel it so that her precious "serious relationship" will be "protected." I think she's nuts, but she seems serious! I normally don't want to upset her, but I see no problem with me dating this boy; this is my social life we're talking about, not hers! Do you agree with my point of view or my sister's? — I Want to Go Out With Him, via email

I WANT TO GO OUT WITH HIM: I absolutely agree with your point of view. The two of you met organically, had a nice conversation and he followed up with you later to ask you out on a date. You already know he has a very nice older brother, and this means he's likely also of good character. You at least deserve to be the judge of that, not your sister.

Many decades ago, in my own family tree we had two Irish women who were sisters, and they ended up marrying two Irish brothers. These couples met in Indiana near Chicago, not in Ireland. Both marriages were very successful and one of the two Irish ladies in this story was my own mother!

I wish for you camaraderie, compatibility and fun on your date with this boy. Do get permission from your parents to go out on any date of course, but your potential date in this case should not be disqualified simply because he is the younger brother of your sister's boyfriend.

I FEEL STUCK IN NEUTRAL

DR. WALLACE: I'll be 17 in a few months, but I already feel like a failure. I have not yet been out on a real date. And besides that, even though I asked my parents if I could start working part time somewhere to earn some money, I still don't have a job.

My parents did give me permission to work up to 12 hours a week if I can keep my grades up and continue to be respectful of our family rules and curfews. I have a good track record with my parents so far because even when my friends and I hang out late sometimes, I always contact my father by text to get permission to stay out a little longer.

So, I'm all set now to date and get a job, but I am still sitting here with nothing because I get too nervous to ask a girl out and I'm too intimidated to go into a business to fill out an application.

What can I do to break out of my shell? I'm thinking that I should just focus entirely on getting either a date or a job, doing one of them at a time so that I can at least get something accomplished hopefully within the next month. Which is better to start with? — I Need to Get My Life Going, via email

I NEED TO GET MY LIFE GOING: You should start by realizing that you need to ask for things that you want in life. Being proactive is decidedly superior to being reactive in these matters. And even if you get nine negative answers in a row on one or both topics, a "yes" on your 10th try will make you so happy that you'll forget all about the nine negative replies that preceded it, and you'll be thrilled with the positive progress you've made.

And once you get the hang of being able to apply for a job or ask for a date, you'll settle into a comfortable position of confidence, knowing that you can interact successfully in society.

I suggest that you network with your friends, family, teachers and anyone else you know to find the part-time job you feel would be best for you at this time in your life. Start with your job search first because your odds of getting a job in today's economy are pretty good currently.

Once you do secure a job, you'll start to socialize with your co-workers, which may lead to opportunities to ask for dates at an appropriate time and place as well. Also network with your friends and acquaintances and don't be afraid to start your dating career with a blind date as a first step. At this point you just need experience, and once you get started, your comfort level and self-confidence will rise markedly. I visualize you being happily employed and going on regular dates in the very near future, likely by this summer.

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 rwallace@thegreatestgift.com. 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.

Photo credit: Filmbetrachter at Pixabay

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