Dear Kiki,

My married friend is getting separated and he’s already ready to get back out there. I haven’t been out there since before he got married. This makes me feel ashamed, but not enough to do anything about it. What WOULD make me feel ashamed enough?

Dear Ashamed Enough, 

OK, first things first: Shame and love do not mix. In fact, barring specific kinks, shame and sex don’t mix, either. So please don’t let shame be a driving factor in getting “back out there.” A relationship begun in shame will more than likely end the same way, which will set your efforts at finding a satisfying connection back even farther. 

Now, you don’t specify in your query, so be sure you’re asking yourself this question: Ready for what? You and your friend may have very different ideas about what putting yourself out there means. If he’s looking for a good time and you’re looking for a long time, it makes perfect sense that you wouldn’t be “ready” on the same timetable. He may be as gunshy as you are about making a new commitment, but more willing to explore his options along the way.

Lastly, even if your friend is getting out there, that doesn’t necessarily mean he’s “ready” to do so. Different people process experiences in different ways. For some — like your ol’ pal Kiki, in fact — spontaneity is the only antidote to calcification. We know that if we wait until we’re “ready,” our brains will lure us into circles of pseudo-logic and self doubt, leaving us unable to act at all. “Ready” ceases to be a productive marker. But for plenty of other folks, preparation is key to security, and pushing forward without being ready leads just as surely to failure.

In short, Ashamed Enough, don’t worry about anyone’s readiness but your own. And if your reticence is leading to loneliness, take time instead to deepen friendships and familial relationships. Those efforts are always time well spent.

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 November 2025 issue.