Nov 19, 2025
The holiday season is here, and with it comes a whirlwind of parties, family gatherings, and let's be honest, a lot of pressure to be "on." You’re constantly switching gears between talking to close family, distant relatives, coworkers, and maybe even a few new dates. Because yes, it's also cuffing season—that time of year when the desire to find someone special to cozy up with can feel extra intense.
Last week, we talked about how to simply show up to these events when you'd rather be anywhere else. But let's say you've mastered the art of arriving early and having an exit strategy. Now you're in the room—so what do you actually say? In all this social hustle, it’s easy to feel like you have to be an open book to connect. Maybe you’ve walked away from a conversation—or a first date—with that cringe-y feeling of, "Whoa, why did I just share all that?" If you have, please know you're not alone. We often confuse total transparency with being authentic, but I want to share a gentle reminder that has helped so many of my clients: you can be 100% authentically you without handing someone the entire story of your life on the first page.
It all comes down to a simple but powerful difference: Honesty vs. Transparency.
Think of it this way. Honesty is telling the truth. It’s saying, "I'm feeling a bit tired tonight." It’s real, it’s factual, and it’s enough.
Transparency, on the other hand, is giving the director's commentary. It’s sharing, "I'm exhausted because my partner and I had a huge fight last night about money, and I was up until 3 AM crying..." It’s the why, the how, and the intimate emotional play-by-play.
Both are real, but one shares a simple fact, while the other opens a deeply personal chapter.
This is especially important to remember during cuffing season. In the spirit of trying to find connection quickly, it can feel tempting to spill all your intimate details, hoping it will fast-track a sense of closeness. But real connection isn't a wildfire that blazes from oversharing—it’s a slow, steady burn built on trust and shared moments over time. As I talked about in my article on building connection, rushing the timeline by sharing your deepest struggles, past hurts, or biggest fears right away can sometimes overwhelm a new spark rather than nurture it.
I like to think of your personal stories like the cash in your emotional wallet. With a casual acquaintance or a new person you're dating, you might share a few small bills—that's honesty. "Work's been busy!" or "I love a good cozy holiday movie." It's low-cost and keeps the conversation flowing.
Saving the bigger, more valuable deposits—the transparency of "I'm terrified I'm about to be fired" or "My last relationship really shattered my trust"—is for those few, trusted people who have proven they’re a safe vault for your heart. You wouldn't hand your whole wallet to someone you just met, and you don't have to hand over your whole emotional world either.
So, how do you navigate this in practice? It's less about memorizing a list and more about shifting your mindset.
You can start by having a couple of gentle, truthful responses in your back pocket for when those prying questions come up. Instead of diving into the drama of your dating life, you could smile and say, "I'm keeping my eyes open! How did you and your partner meet?" See what I did there? You answered truthfully and then bridged the conversation back to them. People usually love to share about themselves, and it takes the pressure right off you.
This isn't about being secretive; it's about being selective. And sometimes, people will notice that selection. I learned this lesson myself with a social acquaintance. We worked together sometimes, and she always pushed for more personal details. I never felt comfortable sharing deeply, so I’d gently steer the conversation to lighter topics. She eventually got frustrated and told me I was "hard to know." Honestly? It stung a little, but it was also true—with people like her.
A few years later, I ran into her and went to say hello. She completely snubbed me, wouldn't even look up. And in that moment, I felt a strange sense of validation. It confirmed everything. Some people have a script in their head for who you should be and how you should connect. If you don't play your part, it's game over for them.
That's their limitation, not yours. That experience was a powerful reminder that my instinct to protect my inner world was right. We were never meant to be close friends. It also cemented this truth: being honest and kind is always the way to go. And if someone has a problem with those gentle boundaries, it just means your instincts to not let them in closer were correct all along.
The goal, whether at a family dinner or on a first date, isn't to bare your soul to prove you're authentic. It's to share moments, enjoy the connection, and see how it unfolds. By choosing honesty over unnecessary transparency, you protect your peace and save your most precious stories for the people who will truly cherish them. You can be your wonderful, authentic self without handing everyone the key to your inner world. Trust that the right people will earn it, in time.