The Ideal Date: Whiskey, Wit, and Just the Right Amount of Trouble

I don’t do boring. Dinner and a movie? Cute, but I’m not here for cute. My ideal date feels like foreplay for the mind, an experience that leaves us both smirking on the drive home, replaying moments in our heads, and wondering, “What the hell just happened—and when can we do it again?”

If you’re taking me out, buckle up, darling. I’m not your standard dinner-and-small-talk girl, and if you’re the type who spends half the night refreshing your emails or checking your stock portfolio under the table, let’s save each other the trouble. My time is valuable, my energy is magnetic, and my standards are razor-sharp.

Step One: The Invitation

First impressions matter. Don’t ask me, “What do you want to do?” Have a plan. Confidence is hotter than abs (but let’s be honest, abs are a nice bonus). A well-placed “Be ready at 7. Dress sharp. I’ve got a plan” sets the tone beautifully.

And gentlemen, let me clarify: “Netflix and chill” is not a plan. It’s an escape route.

No, I want a whisper of anticipation before we even meet. A message that hints at the edge of your intentions, a glance across the room when we finally see each other that says, “Behave—or don’t.”

Step Two: The Setting

Somewhere with atmosphere. A rooftop bar with golden-hour views, a tucked-away speakeasy with low lighting, or a dinner spot where the menu has three options and every single one is perfect. I want shadows and candlelight. I want to lean closer to hear you over the low hum of jazz and feel your breath a little too close to my neck.

Surprise me. It makes me wonder how the night’s going to unfold. Keep it unpredictable but intentional—like you’ve thought about this for over three seconds while waiting for your protein shake.

If we’re in a booth, sit beside me instead of across from me. Let your knee brush against mine under the table. I wonder if your hand might slide casually to my thigh when the waiter walks away.

Step Three: The Conversation

Surface-level small talk? Dead on arrival. I want wit, banter, and the kind of eye contact that makes the air crackle. Ask me about the most scandalous thing I’ve seen on a superyacht (spoiler: you will need another drink for that story), or tell me about a moment in your life that made you who you are.

Let your voice drop when you say something you know you shouldn’t. Watch how I react when your fingers graze mine, reaching for the same glass. Make me laugh, make me curious, and when you compliment me, make it count.

If the conversation’s good, it’s like a slow burn—a fuse being lit. By dessert, if I’m biting my lip and holding your gaze just a second too long, congratulations—you’re on the right track.

Step Four: The Energy

The best dates feel like they could go anywhere. Maybe we end up walking down the beach with our shoes in our hands, or perhaps we find ourselves at some underground jazz club at midnight. The best nights have a flow. Don’t cut it short if we're vibing because of some arbitrary “end time.”

But don’t assume anything, either. The art is in tension. The ‘will we, won’t we’ lingering in the air like cigarette smoke in an old film noir.

If you lean in close to say something and your lips almost—almost—brush mine before pulling back, trust me, you’ll own my attention for the rest of the night.

Step Five: The Goodbye

The ideal date doesn’t drag out awkwardly at the end. Maybe there’s a kiss against a wall that leaves my pulse racing and your hands a little too low on my waist. Maybe there’s a lingering silence, your thumb brushing over my lower lip before you say, “Goodnight, Ivy.”

Either way, leave me wanting more.

And please, please—don’t ghost. If you’re not into it, say so. If you are, don’t wait three days to let me know. We’re all grown-ups here; act like it.

Bonus Points:

• You know how to order a whiskey like a man who knows what he wants—and drink it like you mean it.

• You can hold eye contact long enough to make me shift in my seat.

• Your compliments are clever, not canned.

• You smell good. Like, lean-in-closer-just-to-be-sure good.

My ideal date isn’t about the what but the who. It’s about energy, chemistry, and a connection that feels like electricity humming under the surface.

So, if you think you’ve got the wit, the confidence, and the stamina to keep up with a woman like me—what are you waiting for?

Flirt. Sting. Repeat.

xoxo Ivy