Dear Shan Tell’em,

For the past 5 years, I’ve been sleeping with a woman on and off. We’re not in a relationship, and we rarely talk. But when we see each other we’re intimate. We’ve never kissed or anything, and come to find out she has a few issues with confidence. I suggested that she worked on being more sure of herself, but our routine remains the same. Recently, we made plans to hang out for her birthday, you know dinner, drinks and a visit back to her place. Every time we see each other, we have sex. This time, she’s expecting it to be no different. While I feel comfortable with her, I don’t know if I want to be intimate with her anymore. We literally go months without texting or talking to each other. But whenever we do link up, sex is expected. So I’m wondering if I’m sleeping with her due to comfort or fear of being intimate with another woman. Should I pass and save myself for another female that I actually want a future with? I’m stuck between a rock and a hard place.

Signed,

Pass or Play

Dear Pass or Play,

This is a no-brainer. You’re comfortable. At least you were at some point. Your questioning of the arrangement signifies that it is no longer working for you. I’m going to be honest. This situation sounds like a commitment phobe’s dream! To just have sex, maybe share a meal and spend and few hours with someone without all of the obligations? Sign every person who does not want a relationship up! The problem is that you are not a commitment phobe.

Pass or Play, you’ve outgrown the relationship. You desire more, and she just might not be the one to give it to you. The cycle of going months without speaking and having sex with someone the next time you see them is a breeding ground for detached feelings. Not to mention it can be dangerous for your physical and emotional health. You mentioned that she has issues with self-confidence. This makes a lot of sense. I’m not saying that confident women do not have sex-only relationships. But the fact that you have sex each and every time you see each other is a signal that she may be using it to spend time with you. Or as validation that she is valued in some way. Even if it is for a quick romp in the sack.

While you cannot have confidence for her, you can assist her in building her own. Suggest an outing where sex is not the end result. Take her out for dinner and drinks, but consider not sleeping with her. That’s IF you care enough to. It seems like you do. Note how she responds. If she enjoys the outing without sex, then maybe you can go a little further. If not, then you’ll have to decide whether or not you wish to continue the relationship. As for your issues, whether or not you fear being intimate with another woman is for you to decide. Why would you be? Are you holding on the past hurts? Do you fear actually caring for someone? To me, this whole thing sounds like a waste of time. And you know what? You could actually be blocking the blessing of finding a mate that you’re 100% invested in by dealing with this situation.

Good luck and I wish you the best.

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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 Amazon.com.