The intricacies of intimacy


Dear Dr. Jenni,

My girlfriend has had a lot of past sexual partners. I’ve only had a handful. This really pushes my buttons, and I don’t understand why! I’m actually not a jealous person. I don’t mind if she flirts in public and don’t fear that she will cheat or leave me. But every time we talk about a past partner or experience, I feel super-agitated. I think she’s starting to withhold (maybe unconsciously) information for fear of triggering me. Any tips?

—Put-Off By Girlfriend’s Past

Dear Put-Off,

You might be struggling with fears of inadequacy — afraid you might not measure up to people she’s been with in the past. Since you claim you are not an outwardly jealous person, you may not be cognizant that these feelings exist.

You might be carrying around a social script that states: Nice girls don’t sleep around. This idea stems from a social construction whereby women are not sexual beings. It’s understandable how this message may have been passed onto you from religion, family and/or media. You may want to explore whether you buy into this.

If you think she is withholding information, then tell her you want to have an honest conversation about her experiences. I wouldn’t ask for the whole history all at once, as that might make you come unglued. Rather, ask for different pieces, one at time, and keep checking in with how your body naturally responds. If you feel agitated, try to deconstruct together what about her story feels uncomfortable. Put all possible explanations for your discomfort on the table, even if you feel some don’t necessarily apply to you. You may find yourself surprised by how many sexual scripts lie dormant until they are pushed to re-emerge in relationships.

Lastly, brainstorm together what sexual things you’d like to experience together. It’s fun to start from scratch with one another and compose your own sexual script. Focus on the present and you may be able to let go of the past.

Dear Dr. Jenni,

I have a huge crush on my boss. He is over 15 years older than me and recently divorced. I sense that he has a fond spot for me, but hasn’t made a move or disclosed any feelings. I really like him because he’s smart, powerful and accomplished. The men I date my age seem like little boys. Should I make a move?

—Crushing on Boss

Dear Crushing,

In short, no. While there is nothing wrong with having a crush, the disparity in power creates a huge conflict of interest for you both. If you engage in a relationship, the way you are treated will forever be biased because you are no longer an employee, but rather your boss’s sex toy. When you get a review, he might pass you up for a promotion for fear of looking biased; or give you the promotion because of your personal relationship — which jeopardizes your professional integrity. If the relationship doesn’t work out, then you are both left with tension in the air, and the possibility of being pushed out of your job. There might also be legal ramifications relating to sexual harassment.

Psychologically, there will never be equality because he will always have the upper hand.

If you are that into him, leave your job, then make your move. If he’s not worth leaving your job, then take this crush as a lesson. If you feel that the men you date are too young and immature, consider switching your approach and dating men who are more powerful, mature and accomplished.

Send questions for Jenni Skyler, Ph.D., to Skyler is a sex therapist and board-certified sexologist who runs The Intimacy Institute in Boulder,