Dear Anna,

I could use your help. I rent a parking space during the workweek from a very charming woman who lives in the building across from my office. A coworker connected us through the doorman when I was looking for a space.

From the first time we spoke, there was a … familiarity. She asked if we’d met before. She’s always been kind and a little formal with me — sometimes even ignoring my coworker friend, who rents a space too. She’s gorgeous. I know she’s single. And I swear I’m picking up a little queer vibration.

I’d love to flirt or maybe ask her out, but I don’t want to make things awkward — especially since I see her regularly because of the parking arrangement. How do I make a move without being inconvenient or weird? — Parking Lot Unlocks Crush Kismet

Dear PLUCK,

First of all, I support a parking lot meet-cute. Deeply. Life is short. Romance should involve A LOT (sorry) more unconventional locales.

Second: You’re right to be cautious. This isn’t a one-off bar interaction. This is a woman whose property you are actively using several days a week. Which means the stakes are higher than usual, assuming you don’t want to avoid eye contact while parallel parking for the next six months. (Or however long you’re employed there.)

So the golden rule here is low pressure, easy exit, zero cornering.

Before we even get to logistics, a small reality check: Kindness is not necessarily flirting. Formality is not necessarily tension. And “queer vibration” is sometimes just hope wearing an inner-arm tattoo of a plant. So step one is to gather slightly more data.

Has she extended conversations beyond parking logistics? Does she ask you personal questions? Does she linger? Do the chats stick to polite territory or do they delve deeper? Ask your coworker for a gut check if you’re unsure — usually we (the crush-ers) are bad at sussing out these things.

If there’s genuine conversational energy, then you have a green-ish light to escalate. Gently.

Keep it breezy and optional. No grand gestures. No dramatic confessions between bumpers. Something casual and contained.

Like: “Hey, I’ve really enjoyed our chats. If you’d ever like to grab coffee sometime, I’d love that. No pressure at all — and totally fine if you’d rather keep things as they are.”

Then stop talking.

Do not oversell. Do not explain your sexuality thesis.

See what that does. Does she hesitate or say no? If so, you smile and say, “All good. See you next week,” and you behave exactly the same way you always have. Warm. Polite. Unweird.

If she says yes? Congratulations. Parking lot rom-com unlocked. (Potentially, at least. You’ll have to see how that coffee goes.)

One more thing: Don’t flirt in a way that traps her physically or socially. No blocking her path. Keep it daytime energy. Open body language. Quick exit available.

Also to consider: Ask yourself whether you’d still want to rent the space if she says no. If the answer is “I’d spiral every morning walking past her,” then maybe line up a backup parking plan before you ask her out.

And if you are wrong about the vibe? That’s OK. Adults survive mild awkwardness every day.

Plus, it will only be awkward if you make it awkward. Rejection is only strange when someone refuses to accept it gracefully. If she declines and you continue being polite and friendly, the awkwardness dissolves surprisingly fast.

So shoot your shot — but make it a soft toss, not a full-court press. (Look at me, sportsing! Someone get me a queer metaphor trophy.)

But do do something! The worst outcome here isn’t actually rejection. It’s months of charged small talk where neither of you does anything.

And remember, worst case: You still have a parking space. (A modern miracle in most cities.)

Best case: You have a date and a story that starts with, “We locked eyes over a Kia Forte.”

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