Confessions of a Cruise Director

Do you have a friend that, before any big night out, is a completely annoying control freak who micromanages each detail of the evening and grills each person involved about the facts surrounding each element before it’s even started? Locations, times, back up plans, etc.? In my group of friends, that’s me.

I have been planning nights out with my friends, particularly to concerts, since I was fourteen or fifteen years old. I’d get the tickets, I’d decide who’d get to come, I’d arrange a meet up spot and if someone messed up my plan or if any aspect of the evening was taken out of my hands by the universe or simple human error, I go into action. First I freak, then I start running into the street and hailing cabs, and then I furiously text my next plan to all parties involved.

My grandmother used to constantly tell me, “Molly, you’re not the cruise director.”

But she was wrong. I am the cruise director. We could all flail about willy-nilly for an evening, or we could get somewhere on time, find the ideal space to claim and then, and only then, cut loose. I take this as my responsibility as a friend to make sure that every aspect of an evening is, at the very least, well thought out. If things get crazy once we’re at our destination and plans start to change, I can be spontaneous, but I’m of the opinion that even spontaneity takes some solid planning.

This isn’t a several hundred word confession that I am a pain in the ass with a good heart, it’s a defense of being this way. ‘Cause you wanna know why, guys? I messed up this weekend. I let Jesus take the wheel, and he steered me directly into a panic attack.

My friends from work and I had been planning to see the Robyn show together for months. There were six people going in my group, and I was responsible for three of them. The morning of the show, my friend Michelle dropped off three of the six tickets at my house and then I went about planning our picnic. That’s not true. I went shopping first and bought a bunch of clothes, and then I went about planning the picnic. The indulgence of shopping the day that I was to be responsible for the enjoyment of two of my dearest friends was probably what derailed me. I have a shopping addiction that has started to consume my sensibilities.

My roommate and I made a fabulous picnic. Turkey sandwiches, olives, apples, cheese, Madeline cookies, candies all placed into little containers and tucked inside of my roommate’s cooler. Since I had gone shopping (seriously the biggest mistake of my life), I only had about an hour to get ready, call a cab and be on the other side of town. I managed to do all of that and just barely remembered the picnic as we left our apartment to go to our other friend’s house to pregame before the show.

Once at my friend’s house, I bragged about my picnic, consumed several glasses of wine and a magic chocolate bar. As we were about to leave for the venue, my friend said, “We’re good to go! Molly, you have the tickets, right?”

Dude. You know when time stops and you can see yourself from outside of yourself. Like, you know exactly what face you’re making and what you’re doing with your body language? I knew what I was doing in that moment because I’d seen other people do it, namely my childhood best friend right after my mom and her then boyfriend had dropped us off at a Dave Matthews Band concert in 2001. She’d forgotten her ticket in the car, and as my mom and her dude pulled away from the venue, we had to chase them down the street, waving our arms, to get her to stop. It was a close call, but we made it to the show.

Clearly what I’m getting at here is that I forgot our Robyn tickets. They were right where I left them after I’d gotten them from Michelle, on the corner of our couch and we were all the way on the other side of town, buzzed and with no designated driver. Everything about the plan was right, except for the one thing we needed.

Part of the reason why I am so anal retentive about plans and evenings out is because I can’t be like, human. I hate acts of human dumbness. It drives me nuts when someone can’t find their wallet or their keys or one of the other really simple yet super important things that you need to be a functioning member of society. Someone forgetting the one thing they need is so inexcusable to me that, on the one or two occasions I can think of in my life that I’ve been that forgetful person, I go into “I hate myself”-mode, and that color is so ugly on me. Worse than pastels, and I cannot pull off pastels at all.

I went into boss bitch mode, which is just a slightly darker shade of “I hate myself”-mode. It’s basically self-hatred masked with fear masked with bossiness. I sent my friend off to the venue with the picnic and I grabbed my roommate and told her that we were going to take a taxi back to our place, flip a bitch and come right back, hopefully in enough time to see Robyn’s entrance.

It was a busy night for cabs, so my roommate was subjected to a full fifteen minutes of me sighing heavily, coming up with schemes for how we were going to pull this off, repeating the words, “I never, ever do this,” over and over again, and eventually, throwing my hands up into the night sky yelling, “What the hell?! Who cares?! What are we going to do?! It’s Saturday night! Let’s just have fun!”

Finally a cab pulled over for us and I ran up to driver’s window and said, “Are you down to do some illegal stuff, my dude?”

He nodded, we hopped in, and then we kind of lived the first scene in Drive for the next fifteen minutes of our lives. In seven minutes, our cab driver, who we learned was named Alex, got us back to our place. Alex moved to Los Angeles from Uzbekistan and he likes it okay. I told him that I felt the same way and to go 55 on the back roads because all of the police were on the main streets because of some Day of the Dead situation that was going on in our neighborhood. Another seven minutes later, we were back where we started, except this time we had everything we needed.

Alex, my roommate and a tiny crystal skull filled with vodka got me through the panic of that moment. We tipped him twenty dollars, ran up three small hills, met our buddy and then three more of our buddies, halfway through the second band’s set. I kept apologizing for messing up, but everyone knew that apologies weren’t necessary and, if you were anyone else on the planet except for me, nothing really went all that wrong that night. It was all better than okay, it was a great time.

Still, all I’ve learned from this whole experience is that I’m right to be so uptight. Sure, I can always get myself out of a situation, but it’s better to not be in that situation in the first place, and if that involves making everyone else around me completely miserable until the moment I’ve decided that the fun juice can be activated, that’s fine. Being unpleasant is easier to recover from than being unprepared, especially if your unpleasant demeanor is a byproduct of wanting to make sure everyone has a great time. And I have to do something about my shopping addiction. It will be the death of me.

Photo from

  • Lauren Nelson

    From one cruise director to another, I feel your pain, Molls. The self-hatred mode kicks in, but in the end, you do what you have to do to get back on track. Now, imagine pulling a similar stunt, but driving THREE HOURS to a sporting event and waiting in traffic before realizing your mistake. The only thing that can fix it at that point is a pile of cash. Thankfully I had enough, and a few beers and a handful of Jello shots cured the rest.

  • Leah Brannan

    i can 100% relate to this! i love being the one who organises everything and i am ALWAYS the one who organises everything…to the point where i’m expected to sort out other peoples plans without even being asked, therefore i lose it when people can’t even show up on time! it’s just disrespectful when you’re going out of your way to make sure everyone else is happy. i’m yet to experience the ‘forgotten tickets’ situation. i might die when i do.

  • Elisabeth Miller

    As someone with ADD, who constantly forgets her keys (how do they end up in the refrigerator???), I’m scared of you, Molls;) My friends and I all know what we do well and I’m never in charge of the tickets. BUT, I’m the person who, once at the venue, knows how to get the drinks quickly and find the best place to stand and I can shmooze with the best of them.

  • Kinsey Stout

    This is my life. I work in higher education, and my primary function is to plan and organize… events, processes, anything you can imagine. THEY PAY ME FOR THIS! Because I’m paid for this in my professional life, I find it very difficult not to do it in my “real” life… Though let’s be real – I was always the cruise director – I just found a way to make money at it. The point being: in most circles, SOMEONE has to have some kind of a plan, or you’ll wander aimlessly and people will get bored and super frustrated, no matter how “cool” and “spontaneous” they claim to be. In my circle, when I forego my natural tendency to be in charge, it ends in disaster, and everyone says, “Why can’t we make a decision? Why didn’t anyone bring directions? Did no one buy the tickets?” Even if it is a “let’s just get together and see what happens” kind of night, someone still eventually has to make a suggestion and a plan must unfold. So, this is our cross to bear… It might be annoying at times, but if we didn’t do it, who would? :

  • Romi Viola

    The photo is from Argentina!
    Enjoy the positive side of being organized. Cheers!

  • Emily Johnson

    Yes just reading this gives me serious flashbacks. I once had a boyfriends friends MOTHER drop me (and my boyfriend and his friend) at a bar just to realize I didn’t have my I.D. It was back at the ladies house…. It was horrifying to me. I had to make this woman (the first night I’d ever met her) drive back to the bar.. pick me up.. drive me to her house.. get my i.d. .. then take me back to the bar. It was so embarrassing and I was so upset that I did this. It was terrible! ((side note she coudln’t get the i.d. herself because it was in my purse which was in my boyfriends car.. which was locked.. and he had the keys).

  • Mallorey Bischof

    you are my hero.

  • Beth Thompson Workman

    The new rule is pack the tickets first! My husband and I travel sometimes to see bands we like and we always pack the tickets first so we can’t forget them. Everything else can be replaced or handled but no tickets is not easily solved.

  • Clare Bamford

    This is totally me. I am the compulsive organizer of evenings out. I feel like it’s my responsibility to take care of people’s “fun-having” needs, especially if it was me who planned the event in the first place. Even when I’m extraordinarily drunk I’ve been known to apologize profusely for events that are beyond my control, like jerks stealing our cab on the way home from the bar (who does that?). In any case, I know I’m completely unpleasant sometimes, but If I wasn’t the one who kept everyone in order, who would? None of the people I hang out with, that’s for sure. It’s a dirty job, but someone’s gotta do it.

  • Samantha McLaughlin Hunt

    This is so me. I feel ya girl, I feel ya

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