Ask Shan Tell'emJET Love

Love Advice: Old School Crush

Dear Shan Tell’em,

I’m a 29-year-old relatively attractive single man who has a crush on a woman that I met at a conference a while back. I have been in several relationships, but I have got to admit that I have not felt this way for someone in years. This is like an “I get butterflies when someone mentions her name” kind of crush. Not to stroke my own ego, but I’m very confident and charismatic, and I usually know how to approach a woman that catches my eye. But this time it’s different. I’m not sure if it is cuz I am ready to settle down or what. I just can’t approach her in the way that I usually do. Also, she’s 6 years younger than me. I don’t know why I felt like you needed to know that. I’m writing anonymously because I know that my boys would clown me. What should I do?


Old School Crush

Dear Old School Crush,

Awww. Crushes are cute. And you know what? They don’t have an age-limit either. Correct me if I’m wrong, but it seems like you’ve had a past with women that was a little less difficult than most, and that’s probably because you didn’t allow yourself to invest too much into the relationship. You used your charm to get what you wanted, and honestly, it wasn’t a whole lot, if you know what I mean. I’m not sure how the women felt about your arrangement, but something tells me that you didn’t stick around long enough to actually find out.

But you know what? It sounds to me like you’re maturing. When we actually allow ourselves to change and grow, we begin to behave in ways that are different than our usual patterns of operation. We become conscious of our actions and how they might affect other people. You’re tired of just having empty connections with women, and this young lady gives off a vibe that isn’t like the rest. Or it could be that she is a no-nonsense type of woman who can see through your script. Either way, the old way of doing things will not work in this instance.

Before you do anything, I’d encourage you to take time to think about why you like her. What is it about her that catches your eye? What makes her different from the rest? You mentioned that she was 23 years old. Is she mature for her age? Or does that scare you? Six years is not an unusual range to date.

If you still want to pursue her after processing how she makes you feel and why, then just be upfront. Find a genuine connection and vibe off of that. Being honest will win. Either she will respond in a way that let’s you know that she’s interested, or she will reject you. No matter the outcome, you will be freed of any worrying that you might be doing at the moment.

Good luck and I wish you the best.

Got a question for Shan Tell’em? Email us at or simply comment in the section below! And don’t forget to join us on Twitter every Wednesday at 2PM CST for a live discussion on love and relationships. Keep up with the conversation via the #AskShanTellem hashtag. 

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Shantell E. Jamison is a Chicago-based writer, radio personality, and cultural critic. She’s also JET Magazine’s Digital Content Editor. She’s been featured on WBEZ 91.5FM, “The Monique Caradine Show,” Vocalo 91.1FM, KDKA Newsradio 1020AM, WBGX 1570AM, WYCA 102.3FM, Chicago Now, The Grio, The Black Youth Project, The Gate Newspaper and “Launching Chicago with Lenny McAllister.” Her debut book, “Drive Yourself in the Right Direction: Simple Quotes on How to Achieve Your Best Self” is available now at