I'm Not Sure He's Going to Be a Good Long-Term Fit

By Dr. Robert Wallace

January 16, 2026 4 min read

DR. WALLACE: I'm a junior in high school, and my dating career has been difficult to say the least. I'm a cheerleader with a lot of friends, but for some reason the last several guys I've dated have all turned out to be beyond disappointing.

Recently, a friend of mine let me know that a certain guy was showing interest in me and apparently letting one of his friends know that he might try to ask me out. I do know him already because he's a friend of a friend who has been involved in many group conversations that I was a part of before.

I know him to be lighthearted, friendly and somewhat humorously funny but in a subtle way. He's always a good part of the conversation, but to be honest, he's not the type of guy physically I normally have dated in the past. Apparently from the news I received, he's about to ask me out within the next week or two. Should I give a date with him a try based on the camaraderie we've had in a group, or sidestep going out with him in the first place since we may not be a good long-term fit anyhow? — Unsure How to Respond, via email

UNSURE HOW TO RESPOND: First, you only respond once you're officially asked out, and that hasn't happened yet. You've obviously put enough thought into this, and your sources are indicating to you that this offer might be imminent.

My question to you would be, how do you already know that he may not be a good long-term fit at this point? You only know him through conversations within a group, not one-on-one. I encourage you to keep an open mind, and if such an offer comes, accept it, and spend some time together to see just how attractive you find his personality and style overall once you actually spend some time with him, rather than pre-judging him from a distance.

SHE ALWAYS SAYS SHE IS BETTER OR HAS MORE

DR. WALLACE: I'm a girl in middle school, and a new friend that I met recently seemed to be very nice at first but not so much lately.

The reason for this is, she's always trying to compete with me, and anytime I talk about anything or show her anything I've been doing, she immediately tells me she has something better or has done something better. This is really tiring, and it also makes me feel like not mentioning anything to her in the future because I know she's going to immediately say she's done something better. Should I just accept that this is the way she's always going to be as a friend? It's actually kind of hard to put up with all the time. — She's Always "One Up" on Everything, via email

SHE'S ALWAYS "ONE UP" ON EVERYTHING: What you are describing does indeed sound tiring and not much fun. Friendships are supposed to be about mutually supporting each other, having things in common and sharing fun times and experiences together. It doesn't appear that this is the case in your situation at this point in time.

There's nothing wrong with gradually spending less time with a person that you find to be incompatible, at least for now. At your age, personalities are continuing to be shaped, and some individuals will grow out of poor interpersonal habits gradually, but there will be others who do not.

In the future, seek to spend more time with friends who support you, have a lot in common with you and who you feel you have comfortable and enjoyable conversations with. One of life's great joys is to have good friends, so select them carefully and wisely.

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: Josh Hild at Unsplash

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