The Single Woman’s Dating Playbook: The Intern

The Single Woman's Dating Playbook: The Intern

One of my favorite flavors of men is the quick-witted variety. You know the type. He’s a conversationalist that can keep up with the best of them. A sarcastic, sharp-shooting life of the dinner party. The quick-witted individual has a keen ability to think on their toes, to read a conversation and easily adapt to the shifting context or mood.

It doesn’t take long to identify when you’ve got a quick-witted Bumble match on your hands. The back and forth is electric, he keeps the zingers coming as quickly as you’re serving them, and he doesn’t let you off the hook for a joke that falls flat.

Sometimes, if I think I’ve found a guy that can hang in the banter department, I like to up the stakes and see what he’s got. So a few weeks ago, that’s exactly what I did. I dusted off The Single Woman’s Dating Playbook and activated The Intern.

My strategy and execution are as follows.

Determine Your Audience

As we discussed last week, the most important part of employing a maneuver from The Single Woman’s Dating Playbook is the research. Repeat after me if you’d be so kind; “Proper Preparation Prevents Poor Performance.”

I knew almost immediately that Ryan wasn’t a dud. The conversation was phenomenal and he kept me on my toes. Straight away the banter was a back and forth like I’ve never experienced. I wanted to meet this guy.

I learned quickly that he was smart. He was one of those good guy government employees, the ones’ that wake up every morning re-energized to impact change from within. He was only a few years older than I am and worked excessive hours for far too little money.

If there’s anything I learned about government employees during my time in D.C., it is that they are the epitome of work hard, play hard. They grind so intensely and frequently that when they’re not working all they want is to let loose, talk about anything besides their job, and generally speaking get the most bang for their literal and figurative buck.

Ryan wasn’t looking for a girl he needed to cater to or appease; he spent 60 hours a week placating strangers. After a week of infrequent yet highly enjoyable communication (I refuse to spend hours chatting via text), I had a solid grasp of what I was working with. Ryan wanted to have some fun.

Planning and Logistics

The only preparation needed for The Intern is a strategic location. This date is not compatible with a quiet night in, or a romantic restaurant hidden away from the main drag. No. The Intern demands an audience.

Upon agreeing we should “grab a drink sometime,” I suggested Friday night at a popular bar on Main Street.

Whatever venue you choose for drinks, The Intern has to be activated within walking distance of three to five good bars. This is important.

Friday night dates are tricky. I always advise against planning anything after 8:00, in fact, a 6:00 start time is ideal. If you meet straight after work, both parties are still riding the Friday post-work high, but you can still salvage the night and pull out the old “I told my friends I’d meet them later” if the person’s a snooze fest.

Shoot Your Shot

At 5:45 on this particular Friday, I packed up my computer, grabbed a beer from the office fridge, and bolted to the women’s bathroom. I was running late of course.

I cracked my beer and took an aggressive sip as I slid off my blazer and started to take off my white button down. My pre-date office prep takes eight minutes in total, as long as I’ve remembered to wear my trusted straight-from-the-office date outfit.

I dress formal Monday through Friday, so generally before a date, I’ll wear a white button up over some sort of lace slip, fitted black slacks, heeled boots, and a blazer.

Like always, when it’s date time I strip off my white button down, shove it in my purse, and wear the lace slip as a shirt. If I throw my blazer back on over the lace number (so it’s just sticking out slightly), my outfit somehow goes from corporate ladder-climber to chic/slightly edgy/seductive. Don’t ask me how, I tried it once in a panic and it’s been my go-to ever since.

With four minutes in counting I chug the rest of my beer, take my hair out of a bun and run it under the hand dryer, re-apply my lip gloss (I’m a gloss girl), and spray myself with something that doesn’t smell like Susan’s microwaved Lean Cuisine.

By 5:55, I was walking down the street to the bar. “Be there in 10! Order me a Martini?” I texted Ryan.

I walked into the bar and spotted him immediately. He was more attractive than his photos and my stomach did a little flip as the first date adrenaline kicked in. There are few things I like better than nervous excitement, but upon seeing him I wondered if I’d have the guts to actually follow through on my plan. Could The Intern work if I was all flustered like a little girl?

See, The Intern is meant to make your date think on their toes, showcase you’re equal (if not superior) ability to banter with extraordinary ease, and to see how they do under pressure. The only catch is that it has to be activated immediately. There’s no easing into The Intern – you either initiate upon arrival or bust.

“Hi! Victoria?” he said, and stood up to kiss me on the cheek.

The minute I sat down we launched into conversation; I was trying to determine if my initial read on him was right. Would he be nimble enough to handle what I was about to dish out?

Finally, the moment arrived.

Our waitress came up to the table, looking inquisitively towards our almost empty glasses. “And how are you folks tonight? Do we need another round?” she said.

She was nice, but wasn’t overly friendly. I knew I’d have to prod her a bit.

“Yeah, let’s do another round,” Ryan said, motioning towards my drink. “Same thing, Victoria?”

I paused for a second. “Sure! Why not, it is a first date after all.”

It only took a second until I saw a glimmer in her eyes. I too was a waitress, and if there was ever a trigger word for easy customer chit-chat it was “first date.”

“Ahhh, where’d you guys meet?” she replied.

The silver lining of the whole awkwardly explaining you met on a dating app thing, is there’s always a pause after someone inquires where you met. It is in this pause that I took my god damn shot and activated the play.

“Oh, he’s my intern.”

There it was.

I looked deadpan at her, as if what I had said was complete fact.

In reality, it is absurd to think Ryan is my intern. He’s three years older than me, far more qualified and successful, and probably has two interns of his own. But, that’s the very reason this thing is a playbook classic. Flip the power dynamics on their head, throw a roleplay out there, and wait to see if your date’s quick enough to adapt. Worst case scenario, they make it a joke, laugh uncomfortably, and you look stupid. Best case scenario however, well, is what happened next.

Ryan locked eyes with me only for a second then turned to our waitress. He smiled at her and whispered, “Yeah, so don’t tell anyone. I had to beg her to come out with me. I never thought I’d get to date my boss.”

Our waitress swore she wouldn’t tell a soul and left to collect our drinks. I think she was a little hot and bothered by the whole thing.

I turned back to Ryan and raised an eyebrow. We cheersed and drained our glasses.

“I think I’ll call you ‘Intern Ryan,’” I said.

“As long as I get to call you ‘boss,’” he responded without breaking eye contact.

Oh Ryan, Ryan, Ryan. Welcome to the big leagues, my friend.

The best part about this maneuver is that once both parties are committed, the role play can and should last all night.

Ryan and I hopped from bar to bar. We’d chat with the bartender or other patrons, slowly weaving our complicated story together one ridiculous tale after the next. It was like we were testing each other, curious how far the other could take our little secret without cracking. The Intern is exciting because it’s like a heist only you two know about.

By the time we hit our fourth and final bar I was fuzzy from Martini’s and giddy off our night. We couldn’t stop laughing. The last bartender bought us a round because she said we seemed really in love. “It’s a first date!” I sputtered.

“Yeah, but when you know, you know. You know?” she winked, pouring us shots of what I’m sure was their cheapest tequila.

Full disclosure: The next morning, and a few dates thereafter, Ryan and I would soon realize we weren’t at all right to fall in like, much less love, but on that night we didn’t know that yet. We were just soaking up the high of a goddamn exceptional first date.

The only thing I couldn’t figure out was why he hadn’t kissed me yet. I knew we were feeling each other, so why, after hours of drinks had he still not made a move. He wasn’t the shy type and his hands were certainly familiar with my lower back by bar number four. Sure, I could have leaned in, but I initiated the play! I set our whole spectacular date in motion; least he could do was initiate the kiss.

We left the final bar and he hugged me tight.

“I had so much fun tonight. You’re really cool.”

I smiled back and was genuine when I said, “I had a blast. Let’s do it again.”

And that was that. I waved goodbye and turned to cross the street.

“Wait, Victoria!” Ryan called out. He was walking towards me.

It didn’t take long to realize he had concocted a little plan of his own.

“What happens now?” he said.

I knew immediately what he was doing, but I let it play out. The butterflies were back.

“What do you mean?”

“At the end…” he was close to me now.

“Do boss and intern get together after all?”

They sure do, Ryan, they sure do.

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Life is messy, let's get dirty.

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