I recently pulled a romantic comedy move and slipped a handsome stranger my digits. I was a first-timer to this strategy and it was kind of thrilling. He responded to my smooth moves and in our ensuing text flirtation I almost texted him embarrassing family photos because iPhone + clumsy thumbs = super smooth . So smooth, right?  Here’s what happened.

I was having tea in the Mission, just minding my own business. Except every time I got up, this foxy guy made eye contact with me and smiled. He was super cute— all laid-back business-y in his tailored plaid shirt, funky oxfords, and sexy beard. Yes please.

As we were leaving, I had the unexpected urge to give him my number. I normally would never, but I thought what do I have to lose? Besides my pride, of course. But I was feeling rambunctious, it was a Friday afternoon, and I was wearing big ass hoops and low-slung cords. Why the hell not?

Outside my moxie dwindled. Seems the romantic comedy scene I had in my head didn’t involve me having to actually psyche myself up for the play. For 20 minutes I screwed around on my phone, reorganized the entire contents of my bag, applied lip gloss, and gathered some courage.

For once in my life I didn’t have a pen or paper. Rummaging through my shit, I found peachy nude lip liner and a ticket stub from my de Young museum visit the day prior.

The scenario was becoming even more sexy and glamorous than the idea of actually dating him. I was enamored with my mystery note in peach lip liner. Even better than the 80’s glam of the lipstick was that the ticket stub for was for the de Young’s dazzling Bulgari jewel exhibition.

Note in hand, I marched my booty back in there, and headed straight toward him, making eye contact the whole way. I have to tell you this was very unnerving. I like attention if I’m trying to make people laugh, not if I’m trying to sultry walk them into romance. Stopping dead on in front of his table I deposited the note. “This is for you.”  He gave me a big smile and said thank you as I turned tail and bolted for the door.

Exhibit A for context:


Translation: “I think you’re cute. You should call me and see if we get along.”
(I photoshopped my digits cause I heard you shouldn’t put your private biz on the internet.

10 minutes later I got a text:

Him: Annie?

Me: Haha! You can read my lipstick! Didn’t have a pen.

Him: Yes, tough read, but very admirable job, given the medium. Flattered that you left the note. I live in Austin and leave tomorrow, so linking up could be tough. (Then he wrote more about how he used to live in SF and details, details, blah, blah.)

Me: Haha. Cool. I recently moved here from Austin! Have fun on your travels!

Him: Thanks, have we met in Austin? You seemed kind of familiar.

Me: Maybe? Who knows!

Him: It’s Austin, so probably ; ) Have a great day. Might be out later in the Mission with some friends.

This is where I was composing an incredibly cool and clever response which involved several drafts and re-reads. I was deleting draft #4 of my response when my unwieldy thumbs somehow “pasted.” The item they pasted?  A 20 photo album of a recent family hot air balloon trip. Awesome. Frantically trying to erase, I almost hit Send. That might have gone down as the most fabulously awkward flirtation attempt ever. A mere text of photos but underlain with the message that, “I know we’re just ships in the night, handsome man, but I want you to feel as close to me and my parents as I feel to you. What I mean to say is, well, I love you. So much. If only you had been part of this joyful celebration with my family and I—perhaps even proposing marriage mid-flight!” I should be a dating coach.

Instead I sent this cool Miss Cucumber response back:

Me: Sweet. Maybe I’ll run into you. And that’s hilarious that you’re from my old orbit. I’ve never done that before (the note) and it was kind of fun.

Him: Glad to be your test run. It works for you. Have a great day.

Next missive from him came in at 1:27am:

Him: Hey hey

I didn’t answer, because really, it was too late and cutie with a beard wasn’t on the menu for a 1:30am booty call. And if we’ll recall, I had instructed him to call me and he had clearly texted. Can’t stand a man that can’t take instruction.

What have we learned besides the fact that I shamelessly overuse exclamation marks and Hahas? Turns out the situation was perfect. I got to be risky and frisky with great return and no actual work of having to go on date with a stranger. Win-win-win.

Tell me your tales of random flirtation.

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