Dear Kiki,

Where do I begin? I do not jive with casual intimacy… and I feel like a prude for it. As a young woman I thought if I could have sex like my peers it would be fun and I would feel empowered. While the temporary connections satisfied me in the moment, time and time again casual intimacy has led to dissatisfaction, frustration, in the worst cases some actual trauma, and dare I admit — feelings of attachment and care.

I appreciate that we live in a time where people are liberated to explore their sexuality and have relationships that reflect their values. But… after a particularly heartbreaking and toxic experience I feel lost in the sea of hook-up culture and really turned off from those who participate in it. I feel like Sandy from Grease… I don’t want to hear about hook-ups, I don’t understand why it’s fun anymore, and unlike Sandy I no longer plan to throw on some leather pants and “see where things go.”

I imagine a more beautiful relationship for myself. One where I care about someone AND we have sex but it makes me feel embarrassed and frankly unhopeful. I have great friends, a good job, a lovely family and a zest for life. My life has been so much more than romance, yet a longing lingers and the insecurity of not being enough lurks. I don’t want to be a Samantha, and I’m terrified I’m perceived as a Carrie.

I know I have a lot of love to give and I am working on believing I deserve that in return.

How can I honor my desires for a reciprocal relationship while internally working through the times I let the unspoken pressure to be a “cool girl” come before my boundaries and needs? How does a young woman who’s been through a few things, and who has maybe even put others through a few things get herself back out there without completely retraumatizing herself or planning the wedding before dessert?

—A woman learning to hold her head high while she carries her baggage along for the ride

Dear Head High,

Congrats on all the difficult work you’ve done so far! It sounds like you’ve come a long way in terms of having respect for yourself and better aligning your actions and beliefs. That’s amazing: I’m sure you know this now, but the most important relationship in anyone’s life is the one they have with themself.

There’s two key things to remember as you continue in these efforts.

First: Don’t rush yourself! Our lives are not built on being, but on becoming. All of the characters you reference are snapshots, bound by time as well as fiction. They’re not worth comparing yourself to, because you are not trapped in celluloid. You are changing and growing and failing and succeeding and becoming, constantly and continuously. Enjoy the process! Even the relationship you desire is not an end goal or a credits roll, but another beginning that will change you and help you grow. 

Second: Baggage is endemic. Everyone you meet will have some. Don’t be embarrassed because your baggage is heavy; be proud because you are strong enough to carry it. When you meet potential partners, remember to have grace for their past: That will help you to hold firm in the knowledge that you deserve grace for your own. And know that we are all works in progress, and that’s the beautiful point of it all. 

xoxo, Kiki

Submit questions anonymously at littlevillagemag.com/dearkiki or non-anonymously to dearkiki@littlevillagemag.com. Questions may be edited for clarity and length, and may appear either in print or online at littlevillagemag.com.

This article was originally published in Little Village’s August 2025 issue.