I Need to Find a Subtle Time to Bring This Up to Everyone

By Dr. Robert Wallace

May 18, 2026 4 min read

DR. WALLACE: I'm a 20-year-old college student and the eldest of five siblings. There is an important topic that we should discuss together as a family sometime relatively soon, but I'm hesitant to call a "meeting" because it'll make it seem more formal than it is. It's important, but nothing earthshaking.

I'd like to make sure this family discussion occurs no later than the end of the summer, so how can I best arrange and navigate such a meeting without making it seem too formal? — Anxious to Discuss this Topic, via email

ANXIOUS TO DISCUSS THIS TOPIC: Since we are in mid-May, you probably have at least three and a half months or so to achieve your goal.

During this timeframe, check your family's calendar to see if there are any events going on during this time window. Seek to find a birthday get together, an anniversary, a celebration around the birth of a child or a graduation perhaps. Whatever event may bring your family together could provide an excellent opportunity for you to casually discuss your topic later in the proceedings of that particular day or evening.

I understand your hesitancy to call a specific meeting for your particular purpose, so try to raise your topic during an existing family get-together. This should make it seem more innocuous and impromptu.

I CAN'T WAIT FOR HIM TO GIVE ME THIS GIFT!

DR. WALLACE: I'm 17 and I've been dating a new guy at my high school for the past two weeks. I'm pretty amazed at how well we've gotten along with each other so far and how much we seemingly have in common.

Four days ago, a close friend of mine happened to see him in a jewelry store at our local mall. She carefully observed him from a distance and watched him pick out and purchase a ring.

Needless to say, I have been waiting eagerly these past four days for him to spring this new gift upon me, but so far nothing has happened. Should I continue to be patient or should I just come out and ask him when he's going to give it to me? — Beyond Anxious to Receive my Gift, via email

BEYOND ANXIOUS TO RECEIVE MY GIFT: I caution you to slow your roll at this point! Two weeks is not much time to get to know someone and there's no guarantee at all that what he purchased was intended for you specifically.

If he did indeed purchase a ring for another person, it could be for a completely benign reason (perhaps for a sister, female cousin, etc.) or he could've purchased it for someone else he has a romantic interest in.

Likely it's better to change your focus at this point from any "gifts" to getting to know him better and to ask him some broad questions about his life, background and previous relationships. If the ring actually is intended for you, at some point you'll find out about it. But if it's not, you need to adjust your thinking accordingly.

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.

Photo credit: Aarón Blanco Tejedor at Unsplash

Like it? Share it!

  • 0

'Tween 12 & 20
About Dr. Robert Wallace
Read More | RSS | Subscribe

YOU MAY ALSO LIKE...