50 First Dates: If You Wanna Be My Lover, You Gotta Date All My Friends

Unlike date No. 9, the gentleman on date No. 10 knows how to pick up the check—even when it’s for more than he bargained for.


50 First Dates anonymously chronicles the fun, romantic, wacky, bizarre and downright awful true experiences of dating in Honolulu. Check back weekly for new first-date stories, where to go to woo a boo, tips on where to meet people and more!



What I was looking for at the time

Someone who did not meet the definition of the quintessential f**k boy, college boy slut, ladies’ man, charismatic charmer—you get the hint.


How we met

Through mutual college friends. To be more specific, it was Tinder incarnate, or more commonly known to us pre-Tinder folk as Lulu’s Waikīkī.


Where we went

A dapper little speakeasy bar he works at, where he so delectably creates “artisan ice cubes.”


SEE ALSO: Creating Crystal Clear Ice for Drinks is Not as Simple as Just Freezing Water


The lowdown

I can’t remember how we actually ended up reconnecting after all these post-college years, but we had been texting back and forth to casually meet up for drinks or hang out sometime.


The plan

I worked at a bar, so we talked about grabbing a drink when I was done with my shift. Just a casual, nondescript post-shift drink, typically had by most hospitality personnel. He was going to meet me at my bar, and then we were going to his bar afterward. A bit of a quid pro quo for industry workers.


Or so I thought.


During my shift, I texted my girlfriends the game plan so they could meet up with us, since this was just supposed to be a casual get-together. They tell me they’re on the way. While shuffling about the patio toward the end of my shift, I notice a pair of shiny polished shoes. I pause. My eyes continue up to see a pair of nicely pressed slacks, then the freshly ironed dress shirt and, lastly, the clean-shaven smiling face of my date with perfectly combed hair. Never have I ever gotten dressed up for a post-shift drink. You can tell when someone is dressed to dine and someone is dressed to serve. He was clearly dressed to dine. I was dressed to serve.



“Ohhhh no … ” I think to myself. I realize we are about to embark on our first date.


As we make our way to his bar, I text my girlfriends the predicament, but it is too late—they’ve already found parking. Any Honolulu dweller knows the difficulties of parking, especially on a Friday night, and I will not hear the end of it if I demand they abort the mission. While we await their arrival, he and I sit in a dimly lit corner of the room at a tiny table with a couple of chairs. I nonchalantly tell him that a few of my girlfriends are meeting us for drinks too. Without missing a beat he asks the server for a couple of extra menus. Phewww, OK—he knows this is not a date.


It was totally and conspicuously a date.


My girlfriends arrive and the four of us sit intimately at our tiny corner table, share the small plates he has ordered and sip the fancy cocktails he so proudly concocts during his usual shift. We all graciously get along and enjoy the evening.


How did it end/where are they now?

When the bill comes, we don’t know how we should split it since he has ordered a good amount of food for us all. He reluctantly and respectfully ends up paying for the four of us, while I feel the impending awkwardness that is to follow. But we all end the night on a good note and head home separately, each of us wondering if there will be a second date.


There is. And this time without all my friends.


SEE ALSO: 50 First Dates: He Was Hanging Out Just to Get His Money Back​ 



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