Techniques To Enjoy Comfortable Small Talk

By Dr. Robert Wallace

June 1, 2020 5 min read

DR. WALLACE: I'm a 17-year-old girl and have not yet been out on a date. I'm a pretty good student. I'm reliable, and I eat well and stay away from any and all drugs, alcohol and even vaping or smoking. I look normal, and I take pride in my appearance and hygiene.

My problem is that I don't get asked out on dates. For a long time now, I've wondered why this is, especially since I see a lot of other girls in my grade at school who are similar to me, and they all seem to go on at least an occasional date or two.

After thinking about this a lot, I've come to the conclusion that my situation likely exists because I'm really shy, and I'm not confident in making small talk with people I don't already know, especially boys my age.

What can I do to improve myself in this area? I'm nervous even thinking about having to make small talk with boys, but I'm even more afraid of going through my entire high school years without going on a single date. I have a few friends at my school. They are all girls, and they are equally shy. They are the type of girls who don't socialize too much either.

This school year is almost over, and it's been a crazy one for all of us, but I think we will likely be back in our classrooms in the fall, and I want to be prepared to have a good senior year in terms of socialization and dating. I don't want to end up as an old maid someday! — Girl in Need of a First Date, via email

GIRL IN NEED OF A DATE: If you have been miserable simply sitting out the social scene at your school, it may have been that you didn't "mix" well with other guests because of your shyness.

First of all, do some homework; study who you may wish to meet in advance of taking any action. Look around, and find a few guys or girls you'd like to meet. Learn a little about them. For example, what activities do they participate in? What do their interests seem to be? Who are their other friends? The answers to these questions can be studied via observation and speaking with the friends you do have.

Next, prepare a few (only two or three) questions in advance that you would ask once a conversation is initiated. Maybe ask them how they like a certain teacher, a certain class or a sport they play. How's their coach? How long have they played this sport or participated in this activity?

Prepare a compliment in advance. Do you like someone's new shoes or haircut, for example? Use that as a way to make small talk about how you like something about them, and then be ready to move on quickly to another topic so that things flow and your compliment does not seem out of place or uncomfortable.

Plan in advance for the whole conversation to be only one or two minutes. Explain you have to go to your next class early to study some notes with a classmate (and do have this arranged so that everything you say is true). If you initiate the conversation after school, explain you have to head home and that you'll say hello to this person again later.

Be proactive. You can't simply wait around for someone to approach you. Plan to try a minimum of two conversations with someone new each week. Over time, you will find yourself more and more comfortable saying hello to people as you pass them in halls at your school.

Best of all, the more people you meet, the sooner you will be asked out on a date! There will probably be invitations that come your way to participate in group activities or outings, and this will put you in a position to commence your dating career.


DR. WALLACE: I've written recently to several syndicated columnists to ask each which three classes they took in college that have helped them the most in their careers. I hope to be a writer someday, and I'm at the point of considering what classes to take this fall. What were yours? — Writer in Waiting, via email

WRITER IN WAITING: First of all, good luck to you! Our industry always needs fresh, enthusiastic new voices. The three classes that first come to my mind are expository writing at Knox College in Galesburg, Illinois; public speaking at the University of Indiana, Gary Center; and coaching basketball at Northern Illinois University in DeKalb, Illinois.

Remember, my early jobs were in education and coaching; I only became a columnist after first working for over two decades in public education.

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: sasint at Pixabay

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